In the hyper-casual world we’re living in, any opportunity to add a little smartness to everyday clothing should be grabbed with both hands. One of the most effective ways to do this, I’m finding, is wearing loafers with jeans.
Jeans are what most men will put on as their default at the weekend, and many during the working week as well. It’s then easy to follow them with the obvious partners: a T-shirt and a pair of trainers.
But a casual loafer, such as the Alden cordovan tassel loafers pictured here, immediately make things both smarter and more interesting.
Of course, it can’t just be any loafer. It has to sit some way down the casual scale, as we discussed at length with regard to trousers here.
Suede or a more casual leather like cordovan are the most obvious materials. And often in a more casual style too: not a slim, thin-welted Cleverley, but a chunkier, round-toed Alden.
My particular favourites are the two pairs from Alden pictured here: a brown cordovan tassel, and a Color 8 cordovan full strap. They’re both on the slightly slimmer Aberdeen last, but the Alden make up is rugged enough, and I still wear my jeans slimmer than some. The regular Barrie last would fit with a wider range of jeans (and chinos).
This look has a few different effects that I like.
One is that it adds personality to what can otherwise be a fairly ordinary look - T-shirt, jeans, trainers - without adding bright colours or fashion-driven sneakers. It’s still subtle.
A second is that it stops an older guy looking too young. There’s something about that tee/jean/trainer default that can be a little infantilising.
And a third is that it stops men looking simply sloppy. Of course there are other ways to avoid this, including wearing neater, cleaner versions of each piece, but substituting a loafer for a trainer is probably the easiest.
To me, there is something of the Ivy spirit in a combination like this.
To many Ivy purists, jeans are anathema; to others, a shirt will always be better than a T-shirt. But the playful combination of smart and casual, using easy, practical pieces, seems in keeping with what I take from the original Ivy mentality.
The jeans can be thrown on, and look better the more they’re worn in. The same with a cordovan loafer - quickly slipped on, and tough enough for the park, the rain and the grass, as long as they’re given a wipe down and a brisk buff afterwards.
Why a loafer rather than a boot, by the way? I think just that a boot is more common, less unexpected, and most of the time more casual than a loafer too.
One brand that does this look well is Horatio (above), which makes (to PS) mid-market loafers in Italy and in the Far East.
The marketing is very effective at showing a guy who mostly wears trainers, how good a pair of shoes can look - whether it’s a penny or a snaffle, with black jeans or blue.
Of course it’s also something someone well-dressed like Ethan (below, far left) has been doing forever. But hey, I was always a late adopter.
At the weekend when I get up and go our - often a little too early, to take a bouncing three-year-old to the park - I instinctively pull on a T-shirt and jeans.
I might wear a Cashmere Rugby over the top, often a vintage piece like an M65 or a jungle jacket as well. But it’s the choice to wear smarter shoes rather than trainers that makes me feel most like I’m wearing something interesting, something personal.
In the pictures here, that T-shirt is a PS Tapered Tee, the loafers are a Trunk collaboration with Alden and the jeans are 80s Levi’s (though let’s the argument about rips for another day - a fight like that deserves its own space).
The blouson is not an especially good illustration of today’s point, as there’s certainly nothing boring about it. But it is perhaps a good illustration of the point made a couple of months ago - that there’s some good vintage shopping to be had in Florence.
It’s a seventies suede popover from Hermès, which I bought at Desii this past summer. Suede is not the easiest thing to buy vintage, but it’s clearly been looked after well - there is a slight darkening here and there on the surface, but otherwise it’s unmarked.
Being a popover, it is quite voluminous in the body, especially the waist (see profile image below).
But as we discussed with casual outfits at Pitti, or is the case with the alpaca cardigan I featured from Anatomica, as long as the body isn’t too long, a roomier fit can be fairly flattering.
The jacket cost €700, which is certainly not cheap. But a new piece from Hermès today costs thousands, and of course the advantage of a vintage one is that you’ll never see anyone else wearing it.
I wish Hermès did more pieces like this - more playful in a colourful, Arnys manner, rather than the H stripes and robot prints they define as playful today. Perhaps there’s room there for someone like New & Lingwood to take up that mantle.
Photography: Milad Abedi
You really must offer your Oxford as a popover. That Hermes one looks great.
I have a pair of chunky-soled black weejuns for exactly this . They are great with jeans and a striped Oxford.
If you discuss ripped jeans…Friday afternoon and step away from the computer.
Ha! Alright, I’ll go on a long weekend somewhere.
On the popover, you mean the PS oxford cloth? A different use from the Hermes one surely? I like it in a jacket but it often seems a little fussy in a popover to me – not sure why. Maybe I need to get more into the Ivy side of it to appreciate the style
I think a white popover is a nice addition to a summer wardrobe and goes well with the Ivy sportswear style- although you will lose the slim fit of the PSshirts. I just love the collar on the PS oxfords.
Yeah I know what you mean. Ok maybe we’ll work on a small run. I certainly know what you mean about them in the summer – I like a white linen in that respect, I think because it feels a little like a polo shirt
Linen and chambray popovers are my go-to during the summer months – I find they work particularly well with shorts. If you do decide to do a popover using the Oxford collar, a stripe might be more versatile?
Yes, you may well be right Alex
I thought white as a top layer in summer and a base layer under a knit for winter. But,a stripe would be nice.It’totally subjective,for me-I have plenty of striped Oxford.
Yes either would be nice there
big fan of all shirts pop-over here
I finally found a pair of chunky-soled black weejuns with the price/quality/style I wanted, since you mention them. The are made in England by, they claim, that country’s longest running shoe manufacturer. The company is NPS, a name I’d never even heard of until I saw their loafers reviewed on Reddit 2 weeks ago.
The quality/price is spot on. The design is exactly what I was after: no beef roll on the ends of the strap, smooth-running stitching along the u-shape of the vamp (ie one piece of leather and not two, unlike weejuns that are based on the moccasin design). Chunky soft sole (but not too soft) with Dr Martens-like stitching, sewn with muted silver rather than brash yellow thread. They cannot be mistaken for that better-known player (NPS used to manufacture Dr Martens under license until that company went overseas). And Goodyear welted, but with a fused sole rather than a stiched one (since it’s not leather).
I’m banging on a bit much here I know, but it’s lovely to get exactly what you want (with excellent customer service for the US market) for which I apologise. Simon, you may be interested to review the company, even though it may be at a quality level below your usual target.
Would be nice if you could do a review of the horatio loafers while you’re at it simon (or this was what i expected when you were talking about horatio in the article)
Sure Shem – it’s not really the quality level we’d normally cover obviously, but if there’s enough interest I can do something
I would also be interested but also weejuns would be a very good idea to review since they are the loafers that made me start my loafers-journey. Of course not the quality of alden but if someone has 250 euro to spend a lot better than some trainers. On the cheaper loafers i never use trees and i really dont care to do so so they stay always ready to be worn everywhere (like the common projects pair you used like that). Would the crocket jones shell cordovan loafers fit the style too or are they a bit more formal ? Could you post the link of the alden shoes on the photos ?
The Crocketts do work well in that context, yes.
I didn’t post a link to the Aldens because they’re no longer available from Trunk, sorry.
Are they the cigar cordovan ones? If so, that’s my favorite cordovan color and on an Alden tassel it’s perfection. If they were on the Copley last, I wouldve purchased right away. Enjoy in good health.
Yep, and thank you
A ‘stay away’ judgement can also be pretty helpful. The mid-market space is a real minefield. It’s hard to know what you’re sacrificing…
I’d certainly be interested in a review of Horatio’s. Their loafers have a somewhat different look from Alden’s and they have been enthusiastically endorsed elsewhere (e.g. Jake Whigham).
Cheers Evatt, noted.
I guess it’s pretty obvious to tell the quality – some are welted, some are not, the welted being made in the far east. But more importantly, the price shows the quality level you’re largely working to. They’re not going to be the same as a Crocketts or anything above, which are 100 pounds more. It’s really up to you how much you care about that quality angle?
I hope that makes sense. I always feel like people think they’re going to be surprised by a review – eg saying that despite the price they’re the same quality as a shoe twice that price. But that doesn’t really happen.
I would be very interested in a review and interview with the Horatio boys. They’ll have a great story to tell with a history going back to the original Duffer of St.George shop, Timothy Everest, and the Present shop in Shoreditch. Some great London institutions. Subverting high end brands and mixing them up with vintage and casual gear since the 80s. Get Tony on the case!
The shoes are well made and great value.
Cheers Paul, will do
The shirt looks nice, but can it even be washed or dry cleaned?
The popover? Yes a specialist dry cleaner would be able to deal with it
Not the right post for it maybe but just wanted to say how happy I’ve been with my PS Tapered T-shirts since you mention them in the article, Simon. Very robust cloth, flattering fit. So much so that I hardly ever reach for my Warehouse ones anymore. It would be great to see a grey-coloured version sometime soon. 🙂
Cheers Teo, always lovely to hear. We are working on a grey, don’t worry
Another thumbs up from me – I’ve had numerous compliments on mine
Hi, totally agree on loafers with jeans, however prefer a little chunkier and definitely penny loafer. In my case wine colour Bass Weejuns (repaired countless time!) and tan nubuck but not for wet weather. I do struggle with no socks (one for another column!) though only because of comfort, so tend to go with a tonal pair. Also a couple of old beaten up Sebago dockside’s nicely salt marked – but not really for in town – which I have had for many years and for me are a worthy of ‘how great things age’.
I’d say this look is definitely an authentic interpretation of Ivy.
You can probably tell you’ve hit on a long standing personal favourite on mine!
Regards
You can buy true “no show” loafer liners. They certainly don’t offer any support, but they’re cut specifically for various loafer shapes, if you’re just trying to avoid rubbing or bare feet.
Btw sorry forgot to add I think the whole look Ethan has put together in the photo is great. I just never seem to quite pull it off myself!
Yeah that’s a different level of execution
Simon, what kind of sole do you favour on these loafers? I ask because while leather has a certain ‘something’, it wears through really quickly if one wears the loafer a lot / casually. But then rubber soles have a certain ‘stodginess’ if you will..(!)
I wear leather mostly, and I find if I’m not wearing them every day (so the leather generally can dry out) they last pretty well. But it also depends on the size of your wardrobe.
I don’t mind rubber when it’s the thin, ‘city sole’ kind of one, and I can see the practicality. But given the choice I’d usually for leather.
Although not exactly the topic covered in this article, PS readers, what would be brand recommandations on mid washed jeans, mid high rise, tapered leg (not too slim) ?
P.A. Drakes or Anglo-Italian’s house styles are exactly as you describe.
I recently bought a pair from Drakes and like them.
Thanks David, although I really like the Anglo-Italian ones, these are completely out of budget for me.
I can’t justify paying 250€+ for denim, it will get beaten up, stained, and I don’t care that much about it being selvedge or not.
You could try some Levi’s 501s. Way cheaper than Drakes or Anglo (obviously won’t be as nice, but they’ll do the trick).
Something I really ought to do more. I’d love to get an Alden LHS. I tried looking for slightly more budget ones, but none of them come close enough I think. Will check out Horatio later for sure.
Would you consider these loafers to be too smart to go with jeans?
Probably yes, Aaron. They don’t look like a particularly rounded last, or cordovan or suede
They look very much like Loake Whitehalls. I have that exact same pair and don’t really like how they look with jeans.
Hi Simon,
Beautiful styling, as always. Your eye for colour combinations really is great. Also agreeing on the harmony between loafers and jeans – perhaps best championed by stylish Japanese men (as illustrated by the Ametora cover) and the L’Etiquette team. And especially effective in casual offices.
As a fellow dad, however, I find cordovan leather soled loafers deviate too far from standard dress in the park, and especially so with tassels. First, because cordovan is so shiny that people easily remark ”oh, you are wearing dress/patent leather shoes”, being prominent just as a conspicuous trainer would.
Secondly, because of them being ineffective for the occasion: going to the park involves impromptu running, climbing, loafing around in sand, mud and other activities which require more traction and flexible shoes that stick to your feet. I prefer paraboot-style derbies or Rancourt-style mocs instead. Perhaps a rubber-soled chromexcel penny loafer would work.
It might also be that my neighborhood is less conservatively dressed than yours (appropriateness being relative etc). Nobody wears oxford shoes nor dress shirts in the park, instead people lean into gorp-core, workwear and similar styles. Lots of pile fleece, chore coats and blundstones.
Yeah, I know what you mean RKM, and my neighbourhood certainly isn’t that smart. I guess what I’m saying is that (aside from those practicality points) I like cordovan loafers in that context because everything else (tee, jeans) is so casual, so it largely goes unnoticed, or only very subtly so.
On the shininess, by the way, that’s up to how you look after cordovan. You can just brush them and rub them down now and again, and they’ll never have anything like a real shine, but still be looked after well enough
Thanks Simon,
I guess I will have to take my Aldens to the park and try! And thank you for the tip. I try to aim for a sheen rather than a shine, if that makes sense.
It does, absolutely. All you really need in terms of care is to brush them down now and again (maybe wipe too) so they’re clean, and then rub so the oils come up. And that not very often either
Hi Simon, what do you usually use to wipe the cordovan?
I have noticed there are some water spots. They disappear once I put cordovan cream on, but it would be good if I could remove them after every use.
Many thanks,
Jack
The wiping is more for actual dirt or dust.
For the water spots, try rubbing pretty hard all over with a polishing cloth – it brings the oils back up. If that doesn’t work then you need the cream, but then hopefully that’s only the case when it’s been raining. Also, if you do use polish on the cordovan, it should get fewer of those spots over time
Loafers and jeans have been a default combination for me, on and off, for many years. With a smart blazer and shirt back in the day although that did look a little too “rich European playboy” at times!
Yes, very true! One reason to go for a T-shirt rather than a shirt if you want, but also I think a salutory lesson in the difference that fits make. I’d bet those playboys wore their jeans and their shirts and their blazers pretty tight. Whereas Ethan in that picture is loose everywhere and has none of that association.
Yes it is all about the fit! And lets not mention bootleg jeans circa 2000, way too Jeremy Clarkson in hindsight (yes I was guilty of this).
A PS Friday polo, battered jeans and loafers feels a nice combination.
loafers with jeans is a great look that I employ often, and imo alessandro squarzi is the OG of this fullstrap + jeans look.
where did you find the jeans and what model are they?
They’re Levi’s, late 80s. Bought from a French vintage site, though for the life of me I can’t remember the name. I’m sure it’ll come to me at some point
What watch is that with your t-shirt and jeans?
Details on Wednesday…
Hi Simon! It would be great if you could help with a couple of questions.
1) I had recently purchased a couple of popover shirts in view of it being a good replacement to normal t shirts. What is it specifically that you do find fussy about it and whether than should somebody opt for a normal Oxford shirt rather than going for a popover?
2) Would dark brown suede derby shoes look good dark denim?
1) I haven’t thought about it much, but I guess the question is, why are you wearing a popover rather than a regular shirt? It could look a little bit gimmicky. They can certainly look great, but I wouldn’t recommend them as a replacement for T-shirts for someone without a fairly large wardrobe.
2) Yes absolutely – see here for example. I just prefer a loafer or boot generally
T shirts i have found is one thing I am not particularly comfortable in because my arms are not that built and therefore I try looking for alternatives to tshirt just to respect the social propriety as you have always suggested. Now I have realised that regular casual shirts like Oxford or chambray if dressed with sneakers and jeans would not be huge step away.
Thank you for your advice.
Would your dark brown suede derby look good with mid blue jeans?
Yes, though you might find boots in the same material easier
“In the hyper-casual world we’re living in, any opportunity to add a little smartness to everyday clothing should be grabbed with both hands. One of the most effective ways to do this, I’m finding, is wearing loafers with jeans.” Or not wear denim which is the epitome of hyper-casual?
“To many Ivy purists, jeans are anathema; to others, a shirt will always be better than a T-shirt.” Many stylish men, not just “Ivy purists”, would agree. It’s just as easy and smarter to wear well-cut trousers/chinos and a collared shirt, e.g. a OCBD or Sea Island polo.
I’m fed up seeing the boring and bland, “uniform” of Dad’s jeans, t-shirts, overshirts/chore jackets, sneakers and even baseball caps. To fight it, I try to set an example by wearing smart alternatives at all times. I thought that Permanent Style shared that view but it seems that, sadly, I was mistaken.
Hi Gary,
Wearing loafers with jeans is only one way of course, but one which I know will be relevant to lots of readers. It is also substantially different, to my eye, from the uniform you describe – as one reader has already commented above.
Wearing chinos or tailored trousers would of course be another way, but I think if you’re fighting against denim full stop that’s a little narrow minded. Denim has its own beauty and its own quality and craft.
In terms of setting an example and fighting against the norm, my view was set out here. I will dress how I like but I also never want to be disconnected from my age. That’s how things become anachronistic.
Finally, it is of course perfectly possible to enjoy and wear both a T-shirt and jeans, and the tailoring featured last week. Indeed, some people would say that true style requires that kind of breadth. That was true of Gary Cooper – at home in a tuxedo as in a flannel shirt and jeans – as it is today almost a hundred years later.
S
Hey Simon,
Do you think a similar effect can be achieved with derbies? Perhaps of the more casual chunkier variety?
Jackson
To an extent. A chunky derby is probably more casual and therefore a little less unusual with jeans. They have their own style of course, but it tends to be one of bigger, rounder shapes all over
I personnaly love the raw denim and chunky derbies look, especially the kind of Weston demi-chasse.
You don’t mention your Alden LHS for wearing with jeans. Any particular reason? I’d have thought they’d have been perfect for that purpose?
No, they’re great too. Especially in the sand colour with either mid-wash or white jeans.
I just mention the leather/cordovan ones here as it’s a bit more of a contrast as well, having that slight shine.
How about the LHS in cordovan? If the suede version is great as a casual option in the summer, wouldn’t the LHS in cordovan look great and just as relaxed with jeans, but a notch above trainers?
Yes that’s nice too. Personally I prefer the slightly slimmer lasts in cordovan – like the Aberdeen – but that’s partly personal and partly because I prefer a slightly slimmer silhouette still. Friends wear looser fits and that loafer is beautiful
Sand = milkshake or tan?
Or did Alden used to have sand color as well?
Sorry, tan
Love this piece Simon. I’m just not a trainers guy, but that doesn’t meant that I want to look like an elderly history teacher either (I’m only in my 40s). It’s a hard balance and I find loafers a much safer bet than shoes.
On a similar note, I love the Ivy look and the modish style it gave rise to. I recently bought a Baracuda harrington, and my wife isn’t a fan. She thinks I’ve strayed into costume and I look like I’m trying to hard to force a “look”. I get what she means, but in my head it’s a slight extension of other items I’ve enjoyed for years, like trickers boots, selvedge jeans*, Oxford Button Downs etc.
Any ideas? What is too far, and does it even exist (answers on a postcard).
*(yes, I know that some mods hate jeans)
It sounds to me like it might not be the jacket itself Charles, but what it’s worn with? I.e. all things from the same tradition or style, rather than mixing things up a bit
you may well be right. Much as I like the ivy / mod look and style, I’m not a mod (and I suppose few are). I’ll mix it up more
Swap the Harington for a parka.
Small steps before you get the vespa ,Charles.
I am not convinced.
Jeans signify a rough/sporty/cool look. As such, I think, they work well with sneakers, chukka suede boots and rough derbys with a Vibram winter sole (see the winter edition of Crockett and Jones in rough out suede).
By contrast, loafers are fine, light and somewhat feminine shoes that, in my opinion, work only well with dress-trousers and rather fine chinos.
Further, I find that loafers are typical summer / late-spring shoes but jeans really are late-autumn winter pants.
Thanks Markus.
Each to their own style of course, but it’s that very slight contrast in the styles that I find attractive. Casual clothing is a little different to tailoring in that respect, in that fewer things are clearly appropriate together or not so.
I also don’t mind loafers in the winter, but then my feet never get cold, the shoes may well be cordovan, and I wouldn’t wear them if it was bucketing it down.
Sorry Simon, I did not want to sound that absolute and I see your points on wearing loafers with jeans, just not for me.
As to the winter issue, I have a more “objective” opinion considering my background and I guess the reason is twofold: (i) Our winters are very different from English ones, snow, snow slush, salt and gravel (or ice) on the streets on most days, often needing somewhat higher shoes that snow does not come in from the top, etc. This makes loafers – and anything with a smooth sole (slippery surface) – quite impractical on most days. (ii) Probably due to that background, nearly nobody wears loafers in Austria (and as far as I am aware also in southern Germany or Switzerland) in the winter, these being considered (Italian style) summer shoes. So you would likely stand out with loafers in winter, likely not in a good way because a lot of people would think you misdressed (like wearing only a light cotton sweater when it has 0 degress). But this, of course, only applies here.
Thanks Markus, that certainly makes sense.
Oddly enough, when ice enters the equation loafers work surprisingly well. My absolute best pair of “walking across ice” shoes (outside of my hockey skates) are a cheap pair of boat shoes! Several of my loafers work almost as well. Quite ironic that my snow boots are horrible on ice but my dress shoes grip like a gecko.
I’m good with dressier shoes worn with denim IF the denim isn’t too… ahem… well-loved. If they’re worn and faded, suede is the way to go. Otherwise, I’ve worn cognac captoe Oxfords with (my one pair of) jeans to good effect before. A proper pair of shoes can make denim look fantastic, but no pair of pants will dress up trainers.
I disagree. Your comment may be true for some loafers. But when you look at Alden cordovan loafers, they are really chunky and not feminine at all and cordovan as a material screams „autumn“ for me. Therefore such loafers are the perfect match for denim to my liking. (Btw: in my opinion Alden prices, especially for cordovan have gotten way too high recently. I myself would not pay Edward Green prices for their shoes. So I am glad, I already have two versatile pairs from them.) Cheers
I looked at them and still find – from the photo – rather filigrane for jeans. Maybe loafers are not so popular, where I live (too many thoughts of overweight poorly dressed tourists with cheap loafers, shorts and white socks spring into my mind), or it is just my own personal bias. I wear my two pairs (a tassel loafer loafer in dark brown suede and a mid-brown leather penny loafer) only in summer or late spring, preferably with cream or beige linen trousers.
Are you also from Vienna? Yes, loafers are very unusual there. Except for some gentlemen in their 70s. But I still find my loafers and my styling of them distinctly different from those older men and even more so from the tourists. (Btw: I feel that also our Austrian winters have gotten a lot warmer. The loads of snow that I remember from my childhood in the countryside are long gone.)
The loafer idea with jeans is interesting, but I would restrict it to plain suede with no tassels. I really like those Alden full strap loafers, but regular leather or cordovan is too shiny for this purpose in my opinion. So I’d wear those Aldens with nice chinos or linen pants only for example during the warmer months with or without socks depending on the venue of course.
I appreciate the perspective on loafers. I would be interested in an article devoted specifically to loafers. It’s something that you have been writing about more, and is particularly relevant given a more casual wardrobe. Loafers have come up in many contexts, and as a part of many other pieces, as well as reviews of different styles and makers. My thought would be something like a buying guide, where options, makers, price-points, and uses could be discussed. The idea would be for someone who is looking to buy a pair (or another pair), a summary of the different choices available.
Thanks Justin, noted
Seconded. Something a step down from the Aldens (the price always gives me palpitations) but still durable. Love the look of the Horatio but Simon marked it down on its quality. Am I correct?
And maybe a paragraph about the different options: grain, suede, leather (tan especially) and cordovan colors: #4, #8, whiskey, and cigar.
I find the amount of options overwhelming, and I cant narrow it down to what I “really” want. Unlike with other types of shoes which I find it much easier.
Can anyone help with UK/London suppliers of Alden loafers? In particular the LHS; I see a lot of overseas online stockists are limited in where they can ship the shoes.
Trunk, Clutch, End – the latter certainly has the LHS
Drake’s got some Aldens too. One thing to add is that they all stock different widths of the LHS, so worth checking before buying. For example, Clutch only has narrow width LHS and End only has wide width LHS…and this is not entirely clear from the website.
Cheers Zo, very helpful
Thank you, Simon.
Alden doesn’t allow overseas shipping for most stockists.
What about the 180 by J.M. Weston? Good with jeans?
Yes – not especially my style, but it’s great with jeans
This is only my personal opinion of course, but I feel like leather loafers with jeans are a bit of a stretch for me. Like the equivalent of trainers with a suit. I also kind of associate it with that old Italian Stallion moneyed, but not particularly tasteful, look, That’s probably unfair and limited to the Gucci loafer with gold buckles. Also I’m never sure in our cold climate, with leather loafers, whether sockless is just too naff or with socks is too formal
I think my first step on that ladder would be a soft suede penny loafer, which would be a step up from my casual canvas slip on shoes. Otherwise, for leather, I’m a big fan of Edward Green boots with jeans. Yes, less formal, but quite rugged and can be smart with a high shine (black) or an interesting patina (brown). I’m willing to be persuaded otherwise, so on my next trip to London, maybe it’s time for a suede loafer to be part of my wardrobe.
I get that association Malcolm, and the boots are certainly a safer bet.
With the associations in particular, I think it’s about being self-aware about them, and then either leaning into it if you want to, or changing little elements – like the comments above in regards to fit of those types of clothes.
On socks, I don’t think a short cotton socks is ever going to look that formal really. You could even play with a white sports sock if you wanted, though that might be too unusual for you
I do love this type of look – the Hermes popover is a great piece as well. I would recommend JM Weston loafers as a great silhouette to pair with jeans. Resolute Denim’s instagram channel shows great examples of pairing loafers with jeans in an ivy way. I think the fact that vintage jeans often have more of a mid rise and straight hip pairs well with the loafers also.
Good point George
Suede brogues can perform a similar task (and have the added benefit of surviving the sand they put everywhere in the playgrounds I have to take my toddler to – the Alden’s got pretty scratched up…).
P.s. I’d still love to read a piece on toddler friendly tips.
Hi Simon , I really enjoyed this piece , one of my favourites so far and Its great to read that someone else is wearing jeans and loafers ! I’ve been wearing this combo since the early 90’s when I bought a pair of Gucci snaffle loafers in chocolate brown leather which was, massively influenced by large parts of my childhood and teenage years in Italy.
I wear Alden tassels too and have about 10 pairs, in cordovan and suede , with a few pairs from brooks brothers which are distinguishable from normal Alden by having heel foxing . Your picture of the cordovan full strap, inspired me to try that style and I have been very pleased with that model and now I want a cigar coloured pair of tassels .
I love jeans and wear them all the time with button downs, in a variety of materials , blue and white Oxford, denim ,linen, seersucker, chambray and some stripes , always with a box pleat , or a pique polo in marine , navy or white for the weekend. My London wardrobe is small and everything is frequently worn . I have some navy cashmere jumpers, a few Cushman sweatshirts in white and navy and some outerwear . Some would say my wardrobe is boringly unimaginative ,but its simple effective , comfortable and certainly not contrived .
Your comment about trainers/style and the infantilism on grown men is very true and there’s a lot of older men wearing the latest air Jordan/McQueen/colour combo shoes and more than likely own many pairs and to me they come across that are fighting to stay young stop ageing which is part of the hive/sheep mentality. Which if that’s what they want , great for them , live and let live.
I wouldn’t be seen dead in the same shoes as my teenage/twenty somethings ! And I don’t think I’m that old .
I own one pair of monochrome ecru converse 1970 chuck taylors and that’s enough for me .
Lovely to hear Dan
And my wife thought I was crazy for having 3 pairs of Alden tassels in different colors. Aren’t the Brooks Brother’s ones great? I have mine in #8 shell. My favorite pair!
How do you feel about Belgravia loafers with jeans? I think you’ve worn this combination in the past, would you do so now?
I would, but perhaps more with a dark jean or a white one – slightly smarter jeans essentially
Hi Simon,
Before reading this post, I had expected to see a mention of JM Weston famous 180 loafers, as you previously mentioned here:
https://www.permanentstyle.com/2021/05/what-is-french-ivy.html
A remark on the cultural dimension of this topic. French men, for instance, do not wear the Horsebit laofers, whereas or because, they are usually quite ubiquitous with older women. Even though, nowadays a brand such as Celine does offer them for men. But I guess, they are intended for foreigners.
John
Hey John,
I’ve never personally been a fan of that style of loafer – a little chunkier still, high walled at the front. But it’s largely personal. With styles like that and indeed the horsebit (which I don’t tend to wear either) the cultural side is all important. In the sense that, what you think about the style is almost entirely based on what you associate with it
thats it! thats what i like about my casual footwear ive realised…the ‘high front wall’. thanks for putting words to it. jmweston 180, allen edmond patriot, paraboots reims, even old skool vans slip ons.
I am somewhat of a loafer addict myself. I also think that with jeans, it’s useful to wear loafers with some personality. Of course suede, chunky or red brick soles, horse bit, unusual colors (I have 2 in green), spectators, or pebbled grained. Or even battered to death or close to. Anything to dispel the notion that you are wearing your semi-formal work shoes with your frayed and weathered jeans.
Simon, Please defend the style choice of cuffs / turn-ups on jeans. If the hems are simply folded up, why not have them hemmed to the correct length? Respectfully, to my eye, the look, with retro antecedents, I appreciate, seems effected for work wear. Thank you.
I’m going to do a separate article on this Fred, as there are so many questions about it. But briefly, I think it doesn’t look affected these days because it’s worn by 90% of people. And in terms of hemming, you wouldn’t do so on a vintage pair such as this because you’d lose all the fading on the hem
As someone who owns no sneakers, this is a very natural thing to do, particularly in spring or summer. I have two pairs of Crockett and Jones Harvards, in dark brown suede and cordovan, which I use almost interchangeably with this t shirt and jeans look.
As I write this I am wearing the same white t shirt and jeans, but with dark brown suede Chelsea boots.
Nice. I’ve worn suede loafers, suede chukkas and suede monks with jeans for as long as I can remember (since my 18th actually, I vividly remember my first pair of suede loafers) but I only started wearing my Alden cordovan tasseled loafers with jeans when I saw a very stylish gentleman pull this off in Hong Kong in the middle of the summer and without socks. In fact, this is the reason I went into Tassels to buy my first pair of Alden loafers a couple of days after that encounter! I think it works best when everything else is super casual, so a worn pair of jeans and a t-shirt or very casual shirt
Loafers with no socks (at least in Italy) is considered by punduits of classical style a mistake except for summer unlined models but cordovan shoes do not fall in this category
I think we’re straying a little beyond the stricter traditions of classic style here. Also to be clear, this is with invisible socks, not no socks at all. And the cordovan can also be unlined and very soft (as the Crocketts are for example)
Was going to ask about this! I’ve always found the loafers and no socks too uncomfortable (apart from my Belgians, which I wear a lot). You always do invisible socks? What brand is your favorite? I’ve always found they slip down too often
Yes, pretty much always. Only a tennis shoe and some other lightweight shoes in the summer. Most people do really.
I like the ones at Mes Chausettes Rouges, or Uniqlo for the cheaper option
One problem I found with wearing the Alden full straps is that invisible socks don’t really work due to the low vamp.
I know what you mean, but there are versions of the invisible socks for any height of vamp – the Sagans are pretty low too. If you’re struggling, look at women’s socks too – their ones go so low they only cover the toes
There is an article in today’s Wall Street Journal on a pair of Levi’s from the 1880s that sold at a vintage auction in New Mexico for $76,000. There’s vintage. Then there’s vintage!
Each to their own, but there’s too much contrast in the formality equation between loafers and jeans.
a well written article, as always
just a question about the 5th pic from the top – I am struggling to “like” the denim cowboy cum Italian Stallion shoes look, especially when combined with the limp wrist posture
Can someone explain to me whether this is meant to be “ironic”?
No Higgins, some people just stand like that – including me. And you may not like double denim but that’s just somebody else’s style
‘….. is that it stops an older guy looking too young.’ I’m afraid I’d apply that phrase to the older guy who might do well to avoid having rips in his jeans. Even on women’s jeans, rips look like sprezzatura gone too far. But maybe I’m just old fashioned.
Simon – your timing on shoes with denim is either well researched or insanely coincidental with Mens fashion week being a showcase for the recent onslaught of influencers abandoning sneakers for chunky derby’s like the Alden 990 and others like it
Really? Well what do you know
Simon,
What are your thoughts on horsebit loafers? For some reason, I’m finding them more and more appealing, especially in the black grain leather.
Also, where can I find a good pair of light wash jeans? In my opinion, the look is best executed with a lighter wash as compared to a dark wash or raw denim.
I’m not a fan myself, but I think it’s one of those styles that’s hugely dependent on associations. One other reader here said that where he is, they’re heavily associated with older women. For me, it’s cheap Guccis in the 90s and a rather flashier style of dressing.
At the very least, I think it’s fair to say that it’s a style that you might go off in a few years, or might seem less trendy
And sorry, on denim, mine are all vintage Levi’s 501s pretty much – from Le Vif, from Broadway & Sons, and from Japan. But I’d look at the options in Clutch, at Orslow and Levi’s Vintage Clothing
I have been in love with Alden tassel loafers, both with jeans and dressed up, for a few years now, ever since getting a pair in black calfskin 3-4 years ago. Recently I got a long lusted after pair in Shell Cordovan color #8; they are the famous Alden for Brooks Bros tassels, which have the foxing on the heel. These immediately became my favorite pair of shoes. For a long time, I had preferred the sleeker, slicker look of an Italian style penny loafer, but Aldens slowly crept to the top of the heap, and the beautiful deep burgundy of that #8 shell pushed it over the edge. I have worn them with all levels of tailoring, but especially love them with jeans and an unstructured blazer on the weekend. I have to say, though, they do look great with a suit as well.
Just as you say, they are a perfect amount of chunkiness, while also being fairly sharp, with the tassel being the only adornment on the shoe (besides the foxing on the BB pair). When I got my first pair of Alden’s tassels, I was surprised by how comfortable they are all day long; I think this is due to a relatively long vamp. Not coincidentally (as I wear one or another pair of them all the time), I am wearing my pair of black calfskin tassels by Alden today. I also have them in a light brown color as well, which also go great with denim.
Side note for Simon: great suede blouson! Very cool look. I appreciate the tip that a baggier fit is a good look, so long as it’s not too long of a piece. Excellent advice to heed!
Cheers Ben
Im sitting dressed almost the same in Loafers, jeans and t-shirt. Im a fan of Real McCoys and now your tapered t-shirts but this week I bought a few t-shirts from Uniclo (always good for wear cheap alternate) to keep me going. Then I also bought a few (because I liked the colour) from Gu (Another Japanese(?) cheap shop) and sitting here in the tea-house I have just discovered they have no side seams! As thick/solid as RM and tube knitted all for around $10 or less…. Maybe it will fall to pieces when washed but then Uniclo dont so maybe this wont. Time will tell I guess.
I would have never thought jeans and loafers as particularly unexpected or groundbreaking, but the article and comments seem to suggest otherwise. I’m baffled.
It’s certainly not groundbreaking, but perhaps it has become a little unexpected just in recent years, as so many people wear trainers/sneakers
simply because they have flat feet and have to travel long distances
As I have been understanding Ivy more and more I have been mostly wearing kakis/chinos instead of jeans. Now you are discussing wearing jeans again. Oh my. I gave up on wearing loafers years ago. They would not stay on my feet properly. Florsheim had loafers that had elastic inside that would keep the loafer taunt. Those worked for me back in the day.
I love the look of loafers, but alas, don’t own many, as most models don’t fit my feet well. The problem is probably quite common – high instep, slightly wide toes, narrow heel. I have, however, found a style that is incredibly comfortable, by the company, called Meermin. The loafers are completely unlined and incredibly soft, while still featuring the Goodyear welt construction method. What’s also worth noting is how incredibly versatile they are. Because they’re soft, they can be worn with more casual attire; however, their last is so elegant, they look perfect with tailored clothing and even a suit (unless the occasion is very formal, in which case I’d only wear oxfords). I wonder, why such a style is so difficult to find. So far I only know two or three brands that offer such soft, unlined, “unconstructed” dress shoes. I wonder if, perhaps, the style will become more popular, just like the “soft, unconstructed” tailoring has become mainstream, while only a decade or so ago, such soft tailoring was only available from custom tailors. I’m sure that if more young people tried wearing such incredibly comfortable shoes (it should be noted that any style of dress shoe can be built using the same soft, unlined design), they would certainly wear dress shoes, instead of sneakers or the horrendous “hybrid” styles we see everywhere these days. Speaking of hybrids, do you, Simon, believe it’s just a ridiculous fashion that will pass, or is it here to stay?
I think the hybrids will eventually pass. They’ll become like an old man’s shoe, seemingly for comfort and nothing else
Give Alden loafers a try. If the heel slippage is too much try a heel pad.
I had a success with Carmina for my high instep, even thought the internet says the last is more suitable for low instep. The last is Uetam, but it’s more on the elegant side.
Thanks Simon for IVY insights into jeans and loafers.Its lovely to read your posts.
Any alternatives to Alden full strap loafers.
Alden is difficult to get especially in UK.
I don’t know another good maker of full straps – was that the only style you were interested in?
Would you consider wearing the Harvard in this particular outfit, Simon?
I’d prefer a slightly more elongated loafer probably – this isn’t quite the style for it. But you don’t have to dress for every casual style/aesthetic, there are so many.
All you’d need was a slightly wider jean and a cotton or linen jacket maybe and it would fit right in
May I ask why not?
Sorry to ask quite so many questions on this show across different articles! It’s just probably the priciest shoe I’ll ever buy so want to get it right.
Definitely looking for something that can be worn with jeans and a t shirt and with flannels and a jacket, but at size 12 I don’t seem to ever find aldens in my size
No worries at all, it’s what PS is here for.
The style of them is just more rounded, a little chunky, more at home with a more rugged style of casual clothing. The Alden classic penny is like that too, but different from this longer Aberdeen-last loafer. They’re just different paradigms of casual clothing, as we talk about here. It doesn’t mean yours won’t be wearable with a huge range of clothing
Do you think the cavendish still Crockett and Jones would be a more suitable fit?
The Cavendish in a suede would be a more similar shape, yes, but for how you describe dressing I would still go with the Harvard
Thanks Simon, a always, I appreciate the advice
Do you think a Cavendish in brown calf would be too dressy for denim worn with an OCBD or something like a Friday polo?
Yes I think so
Anglo Italian has a full strap. They used to have it in color 8 cordovan too.
What is the pocket on the left chest of the popover? Is it a large pocket that just sits with the seam going across? Is there one on the right or is it just closed?
There’s one pocket on the left, buttoned. It’s fairly large, but not having the support as you’d have in a jacket, it’s only really useful for something light, such as a cardholder or a pair of sunglasses – not a phone
Sorry, my loafer knowledge is poor but I am wondering whether an Edward Green Picadilly in Mink suede would work with jeans, or is it too smart/pointy? If not, is there an Edward Green loafer better suited to this sort of style?
Yes I think it’s a little smart myself. The Earl or Duke are rounder and have that higher wall at the front. Also a tassel (to me) looks a little more casual
Hi Simon, love your take on this. It’s very topical for me as I have just started wearing this look too. Do you have any thoughts / rules around socks vs no socks with this look? Also do you prefer a cuff or no cuff? And how long should the cuff be? Presumably less fussy compared to trousers but keen to hear your thoughts.
I wear no socks when it’s warm enough, socks when it isn’t, basically!
On cuffs with jeans, article coming soon…
Looking forward to it!
Simon, a great article, really enjoyed reading it.
A question: would you ever wear a tassel loafer with black tie? E.g. a highly buffed slim black cordovan?
Another question: do you ever wear a classic Barbour, e.g. Bedale or Beaufort? They appear a good match for the jeans-loafer outfits.
I wouldn’t, but I can see how some would – it would come under the heading of alternative black tie really, being deliberately unusual.
No, don’t wear a Barbour, but I do wear our Wax Walker. To me I’d always want to wear boots with it though. Maybe it’s because I only wear mine when it’s actually raining quite a bit
Thanks. I can see it being deliberately unusual, but to my eye not more than opera pumps, which I know are super traditional but still look a bit weird and deliberately different today.
Yeah the Wax Walker fits the same bill and do go better with boots, although I do wear a Barbour more often, it’s my main casual jacket in late autumn and early winter and spring.
I’ve been doing this as well, though not really as a conscious decision, more like, “I don’t feel like wearing sneakers, what’s the most casual shoe that I can wear with jeans”.
Mostly because it was (and still is) too warm for boots. I’ve worn canvas sneakers a bit in summer, but for the most part loafers, tassel or belgian (dislike pennies).
I guess I bought the minimalist leather sneakers trend, because I remember I was excited to acquire a first pair (which turned out not fitting too well), then second, then considered replacing the first. But actually meanwhile I had started wearing welted shoes exclusively in the office, and got used to them to the point I now feel most sneakers are too flat, with no heel. So in the weekend I mostly ended up wearing loafers instead.
Hello Simon, just wondering since you mentioned what you put on early in the morning… Don’t you dress a lot more casual in general since you have kids? I pretty much only wear sneakers, jeans and flat front chino’s. I enjoy it a lot because I still wear quality pieces and find it fun to try different things. But having kids really changed my way of dressing a lot.. Wondering what your experience is. Thanks.
It hasn’t changed that, no Jasper, but then I’ve had kids for almost 15 years!
Hi Simon
Hi
I read all of the topics on your page regarding Alden and it’s very informative.
For long time I wanted to buy Alden Aberdeen last tassel loafer and split toe 2210. But I am very confused about the width.
crockett and jones cavendish fits me very well but Edward green Belgravia is bit tight on the arch.
I am wondering if you could suggest me from you experience which width of Alden teasel loafer should I order.
I do apologise for any inconvenience if it may cause. My size is uk 9E for EG & C&J
Kind regards
Gulam
The Aberdeen last on Alden loafers is often quite hard to fit, because the vamp is low and the heel cup fairly large, so it’s easy to slip out of it.
Personally I wear an 8.5E or 9E Edward Green and find the 9.5D works well for me in this loafer, but I may have different foot issues to you, and I don’t own the Cavendish
Hi Simon,
Got a pair of Alden 664 from Clutch Café. I ordered colour 8 in size 9.5US but bit snug on the toe, luckily, they had size 10US in black cordovan. So, after long discussion and suggestions slid it and keep wearing. Its tiny bit loose on the heel but apart from that arch and toe fits in good proportion, don’t get the sliding on hill when put long socks but with no show loafer’s socks, I put insole which help me to hold the heel tight.
Thank you for your suggestion and sharing the knowledge with us.
No worries at all, pleased that seems to have worked out well for you
Hi Simon,
There are two things I found especially interesting about this article.
First of all, I like your loafer and jeans look. I think, at times, we who enjoy clothes can get too bogged down in the minutiae: Last is too slim for jeans! Tassels aren’t casual enough! Jeans are workwear so they shouldn’t be “dressed up”. And on and on. Isn’t there a saying about those who know a lot about wine know everything except how to enjoy it? I think sometimes it’s the same thing for clothes.
Jeans are easy. Loafers are easy. No need to overthink it. It all makes for a relaxed, yet elegant, ensemble which you have ably demonstrated.
Secondly, you made an excellent point when you said the look “stops an older guy from looking too young”. I think a lot of guys fear looking (or being) old or stodgy and that keeps them from embracing more classic (and often much more flattering) clothing, which is a shame.
-Richard
Thanks Richard. I certainly agree on your last point, and on part of your first one – that people often get too bogged down in minutiae.
But I would say that some loafers certainly look better with jeans than others. I think the better way to avoid overthinking things, is to do just as much looking at your clothes and how they go together, and so developing your own eye, as reading about principles. Those who enjoy wine or clothes in that way know just as much, it’s just they’re easier in how the knowledge is used
Hi Simon,
Thank you for another great post. Partially because of it I made the decision to pull the trigger and buy a brown cordovan Harvard from Crockett Jones. I’m having a bit of a challenge finding good socks to pair it with. I like the cream/ecru but I find it hard finding one these days (mes chaussetes rouges and Berg&Berg are out of stock), so would you recommend a place to buy them?
Also if you have a recommendation on which socks to pair with the shoes besides the ecru, I’m all ears!
Last thing, when you say you pair the shoes with white socks, are they truly white or off white?
Thanks!
Tamaki
They’re off white.
But I wouldn’t wear those a lot of the time, Tamaki. Most of the time I’d wear something like a navy or a grey or a tan, whichever was close to the colour of the trousers, or harmonious with it. They would be a short sock (mid calf) and not the finest either. Something like Rototo or AnonymousIsm
Thanks Simon!
If I may still ask: does you mid calf socks not often fall? I feel that all that I previously had ended up falling after a short while, which I don’t find is an appealing look. Does it not happen often with the Rototo socks for you (fyi, mine weren’t from Rototo)
Thanks
Tamaki
It happens less with socks that aren’t that fine, and that are better made, like the Rototo. But it will always happen eventually – that’s one of the appealing things of longer socks, but I think they’re out of place with more casual trousers
Why? The top isn’t visible for both otc and mid-calf socks anyways?
Well, most of the time sure. But half the point of a longer sock is that you don’t show any leg, as that’s smarter and so on. But if you cross your legs such that the skin would show, you see it’s a longer sock, which looks to me out of place. Also the material of an OTC sock itself would often be finer and look a little smart for jeans etc
Hm, I agree for sneakers, where I also prefer to wear retro sport socks, but for any other outfit with long pants and decent shoes – lets say jeans and loafers as the most casual variant – do you really believe a generic pair of socks like these (https://www.falke.com/uk_en/p/bristol-pure-men-knee-high-socks/15415_3000/) would look “out of place”?
For the sake of a simple wardrobe, I have for a long time limited my socks to identical navy and dark grey OTC socks, some off white sport socks, and some invisible socks for shorts weather, and I feel this has served me well.
Personally yes, I think so Ferdinand. I feel strange wearing long socks like that with jeans
Interesting, I guess it’s a personal thing. Regarding appearance, with jeans trouser legs don’t move up a lot anyways so I guess it doesn’t matter. But just to be sure: when wearing chinos with loafers, you want your skin to be visible when crossing your legs? That sounds a little odd to me.
Yes, I can see how it would sound like that. No, it’s not that I want skin to show, it’s that long socks just look odd with trousers like that – bear in mind how many people in the world wear them (tiny) and that their main point is to appear smarter by virtue of being smoother etc
Sorry to insist, I am afraid i don’t understand. Are you suggesting only a tiny proportion of men wear otc socks? Because to me whenever I go to a sock shop it seems rather like at least a third of their offerings is otc. Also, the combination I suggest looks exactly like this (https://www.permanentstyle.com/2019/09/how-great-things-age-the-belgravia-loafer-from-edward-green.html) – aren’t these otc? And otherwise what you are suggesting are midcalf socks that however sit high enough to not reveal any skin?
No worries.
Yes I am – I don’t think I know anyone that wears them, even with a suit, apart from me.
No those aren’t OTC, though they are looking pretty sheer. Also, I have moved slightly in my preferences there – I used to sometimes where OTC socks with jeans, but don’t any more.
In the article, you commented they were Bresciani knee-length socks from Mes Chaussettes Rouges though.
I support your shift in preferences — they don’t look great with jean and Belgravia.
Yeah I got that wrong, they were only half calf
How about this kind of loafers with same outfit of t shirt and jeans?
Looks OK, just consider yourself whether they look a little smart or not
This is my first time investing in a nice pair of shoes and therefore wanted to be sure about the purchase.
1) When we talk about smart slim suede penny loafers then do this shoe fulfill that criteria in terms of its design and structure?
2) Is there any flaw which you could point out if possible by looking at the image?
No, that looks to fulfil those criteria
Just received my loafers and while trying it out with t shirt and jeans the combination becomes a little smart but at the same time it also come out more matured. Quite happy with that look. A couple of questions if you could answer.
1) Would you rate the cardovan tassel loafer and your dark brown suede Edward green loafer on the same scale in terms of formality?
2) Your opinion on combination of polo t shirt, mid blue jeans and smart suede loafers?
1 – I’d say the cordovan is probably a touch more casual
2 – fine, it all depends on the execution
Hi Simon,
Thanks for this post – great read. I was recently reviewing your “If you only had five shoes” article and note your fourth item was a black leather penny loafer. Would this still work in your above examples or would the black clash in this instance? I’m interested in picking up a pair of black leather loafers to compliment my brown tassel pair.
Kind regards,
Black leather can work with jeans, but it’s tricky and more of a look. If you only have those two and want to wear them with jeans then I would consider something else
Wow! I’ve been wearing the Alden Cordovan loafer just like yours with my dark selvage jeans lately AND my dad had the exact same Hermes Suede popover shirt.
I remember “borrowing” it a couple of times when I was in high school.
Thanks for reminding me of the past.
Made me think back in time again.
What would you say to wearing Edward Green’s Piccadilly loafers in antique oak with a pair of jeans? Too formal do you think? I have almost completely stopped wearing suits or formal clothing since I no longer work in an office, but have these lying around. The rest of my loafers are casual. Not sure what to do with them though. Pic is from Google, not my pair. Same colour though…
I think it falls into the category of a little bit showy or unusual, but that doesn’t mean it couldn’t work. Wear a white casual shirt perhaps, a smarter watch, but perhaps a beaten up casual jacket – play around with it essentially, as it’s something where the look is deliberately breaking, or at least toying with, more classic dress
Simon – to be clear, would you feel ok with an Alden 986 cordovan penny loafer in this case? I was considering those or LHS suedes, but I already wear suede chukka boots and wanted a little more diversity in footwear.
Ah sorry, yes I would be OK with that, even though I’d tend to a slimmer Alden myself. The 986 might suit a slightly wider leg jean or chino
Hi Simon,
Are your two pairs of Alden’s in the same size? The Cigar tassels look like a more comfortable fit than the full strap penny’s so I wanted to get your thoughts on sizing! Thanks.
No, the full-strap pennys are a half size smaller – and I’ve actually sized up on a new pair since then! (Selling the old pair)
Interesting. I’ve done the same with my latest tassel loafer and I do get a more loose fit, especially in the collar, like yours above. While this is the case, the length is actually more correct.
Hello Simon,
How do you feel about the collar gape/flaring on your tassel loafers, especially prominent in the second image in the article? Is this something that is determined by the width of the shoe and how much heel slip do you experience on this pair vs. the pair a half size down?
Hey there,
That isn’t ideal, but yes is pretty inevitable with this shape of shoe and my foot shape – the instep and back of my foot is pretty narrow, and the loafer is wide through the middle, and low with a low vamp at the front.
There is definitely a little heel slippage, but over time I’ve come to find I prefer that to my toes getting crushed, and with RTW loafers that’s often the trade-off. Slippage isn’t a big problem if you’re not walking long distances etc.
We discussed this more on this article on Anatomica as well
I might try going down a C width next time. Have you ever used tongue pads?
I have, yes, and they do make a difference, but not a big one. Also make less of a difference the lower the vamp is
Hi Simon, have you ever had to get any of your Aldens resoled? If so, who did you use?
I understand Trunk can arrange for them to go back to Alden, which would obviously be ideal, but is expensive and slow. I’m based in London and can get to the places you recommend in the ‘repair’ part of the site – but the look of the welt is such a key element to an Alden and I worry they’d just do it as a standard resole.
Thanks in advance.
I haven’t, I’m afraid, but I would trust those places listed. I know they’ve done Aldens for others – just mention perhaps that look of the welt, to be completely sure
Thank you!
Dear Simon! Do you know how the tassel loafers from Anglo Italian (made by Crockett) compare to something like the ones from Alden? From what I can see online I would guess the AI ones are slightly more sleek? Still casual enough for jeans but maybe better with casual tailoring than the Alden. I guess there are no big quality differences between crockett and Alden since in the US Alden shoes are not really more expensive. Am I right? Thank you!
I don’t own any of the Anglo, but I think you’re on the right lines, yes. Presuming we’re talking Aldens on the Aberdeen last.
One thing the two definitely have in common is that lower vamp.
Yes, I had the Aberdeen last in mind. Thanks
I went with the Anglo loafers and I like them, but I don’t really see the low vamp. My Belgravias (on the left) are low vamp loafers too then.
Good point, I hadn’t ever compared them side by side. Is the Anglo a bigger size? The shoe looks bigger
Both 8 UK. Probably appears longer because of the stitching?
It’s not really the size I was asking about, more the actual length – one 8 might be longer than another if it has a longer toe shape
You are right. Measured at the sole, the Anglo one is about 0,5 cm longer.
Do you have a recommendation for a
Slightly slimmer loafer with a wide toe box. I am currently wearing the Boston, in a EE fitting, and it still pinches my little toe.
Hi simon on the topic of loafers have you tried sebago? I know its not at the level of many brands covered here but it could be as part of a range of shoes on ivy styling (loafers/boat shoes) like what manish covers because i think everyone needs beater shoes and boat shoes are uaeful to have in the summer. I know jason jules endorses sebago too though not sure if he’s being paid by them to do so
I have and it is an OK make, good for beating up as you say. Still I’d probably go for something like Rancourt or something like Yuketen
How about wearing a t shirt and some white canvas sneakers with some linen trousers?
Does it help it not fall to the lowest casual le el?
Sure, that does help. Depending on the linen of the trousers, I might want a smarter tee, maybe a knitted one
Hi Simon, forgive my silly question but what socks to pair with the loafers? Or without socks? Thankssss!
Invisible socks if it’s hot, so hidden, otherwise something like a mid-grey
Hi Simon,
I really like this look and have been trying to find the right loafers. I think Alden pairs well with denim and I’m between two models: full strap Alden with Aberdeen last in color 8 or the Alden grain LHS in black
https://www.thearmoury.com/products/grain-lhs-ithaca-loafer?variant=32616053440583
I know much of this is personal preference, but what is your opinion between the two? What do you think would pair better with denim, primarily vintage light wash Levis.
Definitely the color 8 cordovan – black is much harder to wear well with lighter denim
I noticed in your Japan capsule collection, you took the Alden LHS and a pair of dark brown Edward Green. Ignoring formal requirements, and assuming you were going for sport coat/denim which pair did you chose most?
Seems you, and others you have profiled, wear the LHS with more casual non jacket looks. And then Edward green/dark brown loafers more typically with sport coat. Each serve a purpose.
Think the question I’m trying to ask is do you find yourself reaching for the LHS with a jacket ever? With faded denim/casual sport coat wonder if the LHS, or <insert style here> is a less elevated, more user friendly aesthetic?
I very rarely wear the LHS with a sport coat, you’re right, but it can look nice – more with a very casual, unbuttoned and unstructured jacket, and a less sharp aesthetic. More of a Drake’s look. They were the LHS style with dark jeans too, which I don’t tend to do, and that looks more casual for the contrast.
I probably wore the LHS more on this trip, but less so with the sport coat and denim where I’d prefer the slimmer EG
Geography teacher chic. A look I like. Indiana Jones crossed with Ralph Lauren.
Thanks for the reply.
Pleasure
Hi Simon – I love this look of popover + light-wash jeans + loafers. It is casual without being sloppy and Ivy without being stuffy.
I know your popover/blouson here is vintage, but if I were to purchase something like this new – i.e., long-sleeved, collared, with a blouson shape (though not necessarily suede)- are there any places you’d recommend? Something similar I’ve been eyeing is the Stromboli from Anglo-Italian.
Congratulations on the 15 years, by the way!
Thanks Andrew! Anglo did do a popover suede jacket – is that what you meant? That would be nice
Hi Simon! I was relating this oldish article to the more recent one on ‘If you only had 5 casual shoes’ and wondered if horsebit loafers that you mentioned here would qualify (obviously not as part of your top 5 or even 10) as a casual shoe. Would you also have a view or information on which horsebit loafers would be the best alternative to the overpriced Guccis? You mentioned Horatio here; would they be better than Carmina or TLB Mallorca’s horsebit versions? Many thanks!
Hey Julian,
I’m afraid horsebit loafers aren’t really my style – they’re a little too fashion – so I haven’t tried any. If the style works for you, though, then they could certainly work in these scenarios, yes.
Hi Simon,
Can you tell me the name of the jeans in the 3rd image? The dark pair worn with the black loafers (assuming it’s you in the photo!)
Cheers
They’re from Blackhorse Lane, the NW1 cut. The loafers are actually Color 8 cordovan – see article here
Hi Simon
Do you think that the new lighter blue BHL jeans would work here (E9 Modern Straight Light Washed Indigo 14oz Spanish jeans | Blackhorse Lane Ateliers – Blackhorse Lane Ateliers)?
Thanks, as always.
Hey JP,
To be honest, my first reaction is I’m not sure they would – that’s a pretty light wash and without that much variation. I’d want to see it in person before having a firm view though
Thanks, Simon.
I really like the colour but agree that it’s a little “uniform”. I guess that I hope that it would fade/crease in nicely with some wear.
It probably wouldn’t do that much if it’s already gone through a fairly heavy wash
Thanks, Simon – I wouldn’t have considered that point,
Love the loafers worn barefoot! Very bold and hot look!
What do you think of that fashionable contemporary look popularised by brands like Blackstock and Weber of wearing a chunkier soled loafer with jeans/chinos and a white sock?
It’s a very coherent style, but it’s not my style. It’s part of a different paradigm of casual clothing with much bigger fits in general, and mostly sportswear
1) In one of the comments you have mentioned that you don’t like colour 8 cardovon in LHS and prefer a slightly slimmer version. Would you say the same about dark brown loafers in LHS design also.
2) Would tan suede loafers look good and casual with darkwash jeans?
1) Yes, but what do you think Tamesh? They’re just different styles, which do you prefer and why?
2) They can do, yes
I am thinking that i would be able to create a much varied and versatile casual wardrobe if i have an Alden LHS shoe in dark brown rather tan but now i am in a bit of a dilemna after hearing your perspective.
What style jeans are those? The cut?
They’re Levi’s 501s, I think 90s, but seem to be a slimmer leg than others I have. Nice high rise though
Thoughts on John Lobb LOpez ? The shape looks quite versatile, and I thought they’d llok as good worn with jeans as with a suit. Kind of like Alden Aberdeens but more original
I like the shape of the Lopez and they can look nice with jeans, yes. I never quite liked the shape of the cutout on the strap. Looked a little lacking in finesse
I see what you mean but to me that’s part of the charm too. Someone not particularly onto menswear will never notice it, but that shape is quite distinctive. Also, they are way better value second hand as Aldens, way more under the radar
Very true. I think you’ll find quite a few people will recognise them, they’re fairly well known, but you’re absolutely right about the shape it’s quite personal whether you like it or not
I also do love the Weston 180 but that’s a cultural thing I guess (a bit less versatile)
True
Hi Simon – I have an old pair of black Gucci horsebit loafers. I bought them because I read that they are regarded as a classic, but I get very little use out of them because I never know what to wear them with. Can you steer me a bit? Can I wear them with jeans? I assume grey or navy trousers are ok, but a suit? Do I just treat them as any other black loafer or are they inherently more casual? Also – they have brass hardware. I know I need to match my belt to them but what about watch?
Hey Bryan,
I won’t be the best resource here as I don’t wear them myself, but I would say you should largely treat them as a regular black loafer, just with an added element which is a bit of extra style or a little more showy/unusual in that way. That also makes them a little less formal, as you say. Fine with a suit or tailored trousers most of the time, but a bit like wearing a jazzy tie – it could be quite stylish, but you wouldn’t wear it to an important meeting.
I will also be writing something on black loafers with jeans soon, so that should be helpful in that regard.
On the hardware, no don’t worry at all about the watch
Great article! Do you know what shop you bought the Alden Brown Cordovan Tassel Loafers from? I’m guessing they are cigar and a special makeup. Thanks.
Yes, from Trunk as part of an anniversary edition with them
Hi Simon,
Appreciate what you’ve said about the Horatios being lower quality, but the Alden tassles are a bit out of my price range.
My bigger concern than quality with the Horatio tassles is the shape – do you think they’re perhaps a bit pointier than the Aldens are? Know it’s hard to judge from a photo, just really want to avoid that awful look of wearing overly formal shoes with jeans!
Thanks
Here are the Horatios: https://www.horatio-london.com/products/tassel-loafer-chocolate-suede?pr_prod_strat=e5_desc&pr_rec_id=97122a7ef&pr_rec_pid=7488808714432&pr_ref_pid=7488808878272&pr_seq=uniform
Hey Charlie,
Yeah I know exactly what you mean. I haven’t seen them in person though I’m afraid and hard to tell from an image as you say. Maybe give them a go, you can always return them?
Thanks Simon, yes totally fair enough.
Just thought I’d check with your expert eye first!
Simon hope you’re well! I’ve searched thru the comments as well with Alden & about 6 Alden retailers and it seems the brown tassel loafers you show us here are the cigar brown? They seem to be an “exotic” model which is only made from time to time and nobody seems to have any in stock or planned. Does that sound that correct? I loved them and was hoping to get a pair but am finding it tricky! I just don’t love the Harvard shape so I might go color 8 or wait… I’m hoping you have a magical solution haha!
That’s right, and yes they are quite unusual I’m afraid, sorry. This was a special make-up for Trunk
Bummer.. but maybe it’ll make the reward all the sweeter! Thank you!
Hi Simon,
I really like this look, but sometimes I struggle to figure out what to wear on top. What suggestions do you have for thinking through this?
What issue do you find Rob? I think an oxford shirt, a T-shirt, a cashmere crewneck and a sweatshirt could all work, smart and casual. You might just change what the jeans and loafers are – from a ripped-knee washed blue to a dark indigo with no turn-up, for example
I live in California, and the style is inherently more casual here. May I ask why you would suggest a darker wash denim with no turn-up?
I think it is a little more challenging in the warmer seasons like spring or even summer evenings. Especially when jackets are not an option
In terms of a t-shirt, do you just wear a thicker cotton t-shirt or finer materials similar to those produced by rubato or stoffa?
Hi
I think the suggestion of a dark denim with no turn-up was mainly for versatility – it’s something that can be dressed up or down.
However, if you’re looking for a decidedly more casual style then Simon’s looks with the paler jeans would work well.
For the t-shirt, if you want to keep it casual a nice thick t-shirt like the PS Tapered T-shirt works well. However, the knitted t-shirts work in a similar way to the dark denim – they have the potential to open up both casual and smarter options.
Love seeing you Simon wearing the dress loafers in jeans. Very hot look! Please do more !