Wearing black shoes with jeans

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This is something I’ve had questions about recently - I assume because fashion generally has taken a turn towards black and, combined with the general casualisation going, black shoes and jeans have become a more common styling choice.

So the answer is yes, obviously you can wear the two together. But not as easily as something like brown suede, and not in as many ways. 

On Permanent Style we tend to assume two things about readers:

1. They want to appear ‘simply well-dressed’ most of the time, in those words we’ve used so often. They want to look good but not stand out. On the spectrum of subtle to showy, they lean heavily towards the subtle. 

2. They want clothes that are versatile. This won’t always be the case, but a lot of readers are in the process of figuring out what they like to wear, or upgrading their wardrobe, and in both cases virtually starting from scratch. Versatility is often highly prized. 

For these two reasons we tend to suggest something like a dark-brown suede loafer or boot as the smart option with jeans (examples above). 

A brown-suede chukka works with every shade of blue jean, from dark to light, off-white and black (with a little bit of fading). And also with a range of smart trousers - greens and tans, grey and navy; cold and warm, muted and strong. 

Plus there's versatility with the rest of the outfit. The knitwear or jacket could be anything from a raspberry shetland to a taupe cashmere, the jacket a cold urban navy or a warm rusty brown.

The result is a classic, traditional look. Brown suede creates less contrast - in terms of colour or texture - with the trouser than almost any other type of shoe. 

You get subtlety and versatility. 

Black is different. It’s not great with warm colours, like that rusty brown, and it can make bright colours look cheap. 

The colour of jeans has to be more particular: rich blues usually aren’t great and white can look stark. The easiest colour is a dark indigo (perhaps in a colder, greener wash) or a much more faded blue, like my jeans above.

And it makes demands on your other clothes. Wearing a similarly dark navy top, as I am in these images, can work, as can black itself. Very pale colours are often good, as are some browns or greens. But fewer things work than with brown shoes. 

Black shoes are not as versatile.  

Nor are they as subtle. Black shoes contrast more with these pale blue jeans - they’re not the normal or expected choice. Of course, that’s why some people find them refreshing, but it will suits fewer conservative readers. (It's no coincidence that classic tailoring is more about harmony and has less of this dissonance.)

Black shoes with black jeans creates less contrast, but it’s still more of a look. I like it and I wear it, but the same things apply as above: I wear it less, only with specific things, and when I want a specific style. 

How much of a look it is depends a bit on the type of shoe. The suede Sagans (first image below) are more of a look than the Galway boots (second image). 

But still, my default is something subtler like Color-8 cordovan. 

When it comes to the type of shoe, more casual styles like boots and loafers are generally easiest, as are derbys. But the material doesn’t necessarily have to be that casual. 

While I normally go for my black Utah loafer from Edward Green (a waxed and tumbled leather, a bit like a grain), black calf isn’t necessarily bad. It just creates more contrast and probably requires something a little smarter on top. 

The only thing to be careful with is black suede, as the way it sucks the light can make it quite unusual. That's best in particularly casual styles, like a derby. 

The loafers I'm wearing are vintage Ralph Lauren crocodile loafers. Blake-stitched, probably from the late 1980s, I picked them up on eBay having seen a pair on a friend. They’re not something I’d wear all the time, but the super-low vamp is quite appealing. It might have been good to lengthen the jeans by a fold though, given how low they are. 

Lucas (on the left) is wearing vintage Gucci horsebits. The fade of his black jeans is a good example of how good that shade is with navy, as well as how much easier faded black is to wear in general (being basically grey at that point).

Clothes shown with my blue jeans:

  • B&Tailor bespoke overcoat in Fox cloth
  • PS watch cap in navy
  • Rubato navy lambswool crewneck
  • Vintage Levi’s 501s
  • Rubato black alligator belt
  • Vintage Ralph Lauren crocodile loafers

Clothes shown with my black jeans:

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Hey Simon – what size do you wear in the Rubato knits?


I have a pair of black suede chelsea boots that I sometimes style with black denim, black alligator belt, black leather jacket and a black denim shirt. Its definitely ”a look” but the different materials make it quite good. I could – havent yet – added the black PS watch cap.


Evil cowboy’s day off


On the subject of jeans what cut to you advise for middle aged men (over 40) ?
I’m at an age where I think I prefer regular to slim to avoid the Jeremy Clarkson look .

Any particular cut in the Blackhorse Lane jeans you’d recommend for a 6ft tall, 13 stone , 50 something ?

Jim Bainbridge

Jeans fall into three extremes for me, they’re either very slim and tapered or very wide (neither my style, but it can work), or a classic 501 style that’s comparatively slim particularly in the hips, but mainly straight – and having the appearance of being made for hard work rather than to be overly stylised. Anything that can’t decide which of the above it wants to be, is likely to look bad.

I find that jeans are most likely to look old man-ish if they look as though the wearer has bought them as tailored trousers, not realising that they don’t drape in the same way. So instead of being roomy, they’re baggy, and they have a half or full break which just ends up being a crumpled mess.

Andy Spade looks amazing in jeans – and usually in a simple and timeless way rather than an older person dressing as a younger one.

Tim J

Hey Robin & Simon,
The E5 Relaxed Tapered cut in BHL may also be worth considering. The taper below the knee is not at all dramatic and the cut is quite generous in the thigh. I fit precisely into the same category Robin and can certainly vouch for the E5s

Max Alexander

Robin, my personal take as an older guy is that jeans are one area of menswear where I shop with (and trust) my girlfriend. Although she’s a clothing designer (womenswear), I generally make my own sartorial decisions; we have a truce that way. But with jeans, I find another eye is helpful for finding the best fit. In my experience the biggest issue with jeans is the seat; depending on the cut and your personal butt, they can fit great down there, or look too baggy. I would advise trying several brands in person, with someone else in tow, or at least at a shop with knowledgeable salespeople. Best of luck!


A great Easter read, thank you. Your oft’ reference to cordovan loafers is always in the positive and very much inadvertently pushing me in that direction. If you did a PS collaboration with Alden it would be a big hit I’m sure..!!! Thanks again


Simon, it would be very interesting to hear more about the lack of capacity at Alden. Not sure if it is correct, but I have heard that Alden had to lay off some workers during covid and now cannot cope with increased demand and have more than a year leadtime on e.g. the LHS loafers. Are those loafers really that unique that they cannot find new employees to sew them? It does not really make sense to me. Many thanks in advance.


Yes, that make sense. It is interesting that the theory of increasing prices, and salaries, until demand equals supply does not work in practice. I am desperately looking to buy a pair of Alden loafers myself.


I think this is tough to pull off with a low vamp with kilties. I would prefer a clunkier JM Weston if one doesn’t mind the French Ivy vibe.


Simon, may I ask what your opinion is on the JM Weston 180 loafers? I am torn, since I used to find them too clunky, but they are groing quickly on me. They also seem to be of high quality and to have a true cult status in France.


I would say the 180 is great with chinos and jeans but too clunky for more formal outfits. I have two pairs, in brown and burgundy and I am thinking of getting black ones two wear black shoes more casually.


If you have 7-10 other pairs of loafers then there is a place for them in your wardrobe. But it’s also cultural, the French men and women alike love their high vamps..

Eric Michel

Black loafers and black boots work very nicely with dark jeans, and I wear this extensively when going out in the evening. Personally, I never wear oxford or derbies (black or brown) with jeans. Why? I just do not like it and much prefer loafers, boots or more relaxed shapes like paraboots (great in black..). Only exception: monks! And again I do not really know why but it kind of work for me…


Thanks Eric for your thoughts. The comments are super educational IMHO.

If I may ask – so monks work with jeans for you? Sorry not clear from your comment to me.


Eric Michel

Sorry if it was not clear, but yes, I can wear monks with jeans, as an alternative to my preferred options of loafers and boots…


So your boots are oxfords? Or Chelsea?

get into boots each winter but all mine are derby


My humble take on this: my shoe collection has gravitated mostly towards the poles of black calfskin and brown suede. I have no problems wearing an informal style of shoe (penny loafer, long wing blutcher, split toe shoe, etc.) in black with a more casual outfit, and prefer it to brown calfskin. The primary thing is the style of shoe: for example, I wouldn’t wear a captoe shoe with a casual outfit. And I’ll always prefer suede to calfskin when I want to wear a brown shoe. Admittedly I never really wear blue denim jeans; all my denim is black, grey, brown or tan.

Jim Bainbridge

I love this look. A faded and battered 501 with a sleek loafer or boot in polished black leather is the ultimate in high/low, for me – certainly the one that has the most potential to be rakish if that’s the intention.
Also, great one for womenswear parallels – where wearing black shoes with denim is often very natural and not overthought.


Nice article. Very relevant at the moment. Most of my shoes are brown at this point but I find myself gravitating towards my black calf C&J Bostons all the time these days. I dress more casually and I feel this is the easiest way to dress up an outfit and make it look a bit more interesting and fresh. Heavily washed jeans or some dark denim feel quite easy to wear but I have some black faded jeans and I find it difficult to make a nice outfit with them. I usually end up doing an all black outfit or just wear a dark navy or brown Rubato knit on top.


Thank you for this post, Simon. I had been looking forward to it. It all makes sense. I tried to wear my EG black calfskin Piccadilly loafers together with medium wash blue jeans, and they are too smart for these, despite being loafers. The loafers do dress up the jeans, but so much so that they stand out. My color 8 cordovans or perhaps a black suede or Utah calf would be more aligned.

Michael Powell

I’ve worn black shoes with jeans since the invention of black. But it was always black gym shoes, black casual shoes or black desert boots. Never black dress shoes. I’ve also worn brown, green, or red shoes with jeans. And when I;m feeling daring…BLUE.


In my opinion the best footwear for jeans is to pair a black leather chelsea boot. Second would be a heavy lace up. Personally I’ve never cared for jeans with loafers, regardless of the colour.


I feel similarly. I wear loafers more than any other shoe but with jeans they just don’t feel quite right to me. Jeans are rugged trousers designed to withstand abuse and loafers are basically just slippers made for wearing outdoors. I know most people don’t wear jeans for cattle ranching or manual labour these days, just as most people who wear dive watches don’t go scuba diving, but I think it still looks better if jeans are worn with something that harmonises with their rugged origins like Chelsea / chukka / desert boots.

Tim J

Hey Simon,
Separate to my response to Robin’s denim dilemma, I thought I’d write and say how satisfying I find the 2 x outfits you’ve used to highlight the points you’re making re: black shoes.
I have one of your Bridge Coats and often wear it with a navy crewneck and faded blue Jeans. Somewhat of a staple for me over the colder months.. But I really like the combination of the Rubato knit, black jeans and Tweed in the other images. They’d look great with Lucas’s faded black jeans too, but I think it’s something about the particular colour of the Rubato knit that ties it together so nicely.
Both outfits would work with dark brown boots or loafers too, so I still think you could pitch that there’s versatility here given there are other uses for the black shoes and both outfits.


Could the socks be the natural wool socks from Rubato? Would be funny, as I love wearing them with my light blue jeans, and I thought about them immediately when I saw this post.


Ok, I thought the colour would be neutral enough. https://www.atemporubato.com/products/rubato-wool-socks-natural
To be fair, I was usually wearing these socks with alden colour 8 shoes and the dartford-wash jeans from fullcount. Might not be equally good with black shoes. I will try and report.


Speaking of jeans simon, I think workwear style bottoms are really all the rage with high low combos (e.g. bryceland double knee pants). Have you tried carpenter jeans simon? I see a couple nice ones on etsy/ebay but am hesitant to pull the trigger as I have never tried one. I like my pants high and wide (e.g. army chinos/ olive cargos) but not sure if wide legged denims in such soft fabric looks odd.


Hi Simon, sorry if I missed it but what are the black boots shown in the imagine before the one of you and Lucas? I’m sorry to say that I’m not keen on the RL loafers. I think the low vamp combined with your relatively small feet is not a flattering combination.


My personal view is that black leather shoes with jeans doesn’t work. The only thing that could make it even worse would be to add in a pair of white socks.

Eric Michel

Loafers always need to be a bit smaller than other shoes to feel comfortable, especially with low vamp. It always hurt for few weeks when bought new! I find those RL loafers beautiful, but impossible to find anything comparable at a decent price!


I’m over 60 so I never wear sneakers, blue jeans, sweatshirts or baseball caps to avoid looking tragic. But I do wear denim in other shades (black, white, brown, green..) and I’ve discovered Solovair shiny black penny loafers go perfectly even with black and with white. They’re an epiphany, and IMHO they go so easily because they have a perfect commando sole – not ridiculously high, just right and therefore definitely not formal.
[just to add to the comment about the style of the shoe being key, even within the sub-category of penny loafer]


Not to make you feel old, indeed we’re all headed down the same path… but my father, now in his ’80s, has also never worn a pair of jeans and I appreciate the associations you have with them. I’m in my fifties, and… what I can say is that at this late date they have zero rebelliousness left in them, their anti-authority aspect is long since worn out, decades ago… and yet, they’re not bad looking. How’s that for a compromise? Ha, ha!
As for denim in general, I think denim jackets (say some ’50s or ’60s era Lee Storm Rider) look great with corduroys or wool pants and more casual leather shoes of some sort. Keep the denim above the waist in other words, though Simon’s outfits here are difficult to criticize.


Amen to keeping the blue denim above the waist – I regularly wear (blue) denim shirts. I also came across a very cool denim sports jacket which I really enjoy.

Tom in New Hampshire USA

This article was particularly interesting to me. I am 72, so not interested in high fashion or standing out, but discreetly looking good is still important. I frequently wear well worn Levi 501s in a dark wash. I have plenty of dress shoes, and I hate to see them unworn. I have discovered that some black shoes work. Specifically, low vamps seem to work, as they do on you. Bit loafers seem to work, as shown on Lucas. I also find that a pair of very beaten up tassel loafers work, because they are creased and adapted to the shape of my foot., and have lost any chance of being mistaken for a dress shoe anymore. I also find the high/ low aspect important. The shirt and jacket matter. Black shoes with good old New England flannel shirts don’t work, but they seem to with well weathered Oxford button downs and a country sportscoat. Granted, I live in a rural setting and only dress for forays into the nearby market town or Boston. Thanks for the insightful article, helping me parse out my own wardrobe choices.

Prince Florizel of Bohemia

Regarding Galway boots, did you ever have an issue with metal eyelets? I have got several pairs of winter cotton trousers and metal eyelets ofy boots tend catch the folded fabric inside the trouser leg. My trousers are not tapered, they have regular to slightly wider opening. Is there a cure? It’s rather annoying and I had to have the folded fabric sewn back on. Thank you

Prince Florizel of Bohemia

Yes, speed hooks. I’m sorry, English isn’t my first language. Thank you for replying. Will try to do that.


I don’t really know whether this qualifies as permanent style in the sense you use it, although it certainly is a popular cultural classic, but for black shoes with jeans I think you need to go chunky. Conveniently this matches the sort of casual black derbies and loafers which are (dare I say it) in fashion at the moment. They are also consonant with slightly wider jeans.

I admit to being parti pris as I simply do not like low-vamp, slim-soled loafers; but even making all due allowances I think they are at their worst here as they are out of balance in style and proportion.

Peter Hall

I pair black RL moccasins with mid blue or dark jeans. I think black works much better when it has lost a little of its sheen and is edging towards well worn.


Interesting article thank you. Good to hear your default is more colour 8 cordovan, as that’s exactly where I am with my Alden split toe.


It’s fascinating how many people still think black shoes can never be worn casually—including a certain prominent blogger who thinks of black penny loafers as necessarily too formal to wear with jeans. And a lot of people just told me you can never wear black and blue together at all, which… is so confusing, that’s a rule specific to certain contexts in tailoring, people just hear a “rule” once and take it out of context and treat it as gospel.
Anyway… Yeah, I think a good black pair of loafers or tyrolean shoes or chelsea boots or galways can be much more versatile than a lot of people think. Your crocodile leather, or suede, or any pebbled grain, or black shell, or any well-worn black like those Guccis… you really *can* dress it down.
I’m not personally a fan of your cap toe derbies, though… not that they are necessarily formal, but I just find them boring, they don’t add anything to the outfit except their generic dress shoe last. Maybe because so many men buy generic derbies from… Marshall’s, or Nordstrom Rack, or whatever, and wear them with everything, or did in my childhood. Loafers have more character to them, they feel more fun. Maybe that’s just me.

Max Alexander

Fun story Simon! Definitely a trend as witnessed by Ethan Newton and others. Reminds me I should wear my black tassel loafers (Johnston & Murphy from 30 years ago when they were still made in USA and good quality) with jeans more often. That said, with denim out on the town (Rome) at night, I sometimes wear these derby spectators I had made by Rozsnyai in Budapest. Buffalo hide (blue) and deerskin (beige). Granted not a look for every day, or for everyone…


Obviously a matter of taste, but I’m unlikely to wear low vamp loafers at all. And certainly not with turned up ”wide” jeans as in the first picture. Disregarding any high/low combinations, the proportions are just to off for my taste. I’d rather wear red Balenciaga sneakers to black tie. But then I’m a humble worker who’s never been to Pitti and will never make a living in means wear.

I do wear black boots with jeans though and quite like it.


Of course the fact that black footwear works so well with navy sweaters or coats is no happenstance. It has an awful lot to do with the associations we have with clothing. Black footwear has a centuries-old military uniform past as does the navy pea-coat. Gray pairs well with black for the same reasons. Meanwhile the jeans with black footwear is classic ’50s grease monkey/ rockabilly stuff… revived a bit too heavily in my teen years in the ’80s… but it still works nicely I think.
Sorry if I’m stating the obvious here, my only point is I think the reason certain clothing/ footwear combinations work is just as much for some mystical, out of reach, color theory reasons, as for clothing history. And, yet, maybe — history aside — there is something magical about certain color combinations.


Ah, a great article in your link, thanks.


Absolutely true regarding associations! I decided to wear my black Belgravias with a pair of British Army Lightweights after realising that olive wears well with black boots (something I should have known considering I was a conscript).


Quit hogging all the clothes, Simon.
The poor fellow behind you, statuesque as he may be, doesn’t have a thing to wear!

Ben R

Conversely, do you think you could wear a brown suede loafer with light grey to mid-grey trousers and a black jacket?


On a vaguely related point… I have made the occasional impulse buy from C&J sales and have ended up with two pairs of shoes similar to the Westgate model, one in a tan calf and the other in what was supposed to be dark brown but more a mid cold/dusty brown and I struggle to pair them with trousers.

The calf I wear occasionally with light grey tropical wool in summer but really struggle with the suede given the informality of the colour/material but formality of the last. Any suggestions would be appreciated as I still like them but would rather wear them than admire them on the shelf.


Basically yes… too formal for very casual trousers/jeans, though have worn them that way, and too informal for smart/dark trousers. I’m sure white/offwhite works but feel that look isn’t very fitting for London and hence limited to light grey tropical for calf but not sure suede even works there as they are formal trousers.

Had hoped they may work with things like Drakes games trousers in olive/sand as these appear often on eBay/Vinted so within my budget but I’m bad with colours and concerned they may be too similar tone to work


I have a pair of Westgate in dark brown suede and actually find them very versatile. I wear them with grey flannels, beige cotton trousers, etc. Could also work with jeans, unless they are too wide or too narrow, I believe.


We often hear that in traditional menswear the word “sexy” is frowned upon. I cannot think about black low vamp alligator loafers without this term. It is also distinctly “french” to my eye. I immediately think of those well dressed french women like Emmanuelle Alt. They seem to wear black shoes with jeans far more often than anything else.


Great article Simon, love the outfit. Also, you wear the Rubato black alligator belt so often you might have to do your own PS version of it! It’s rather difficult to find an equivalent belt that nails all of the different elements so well.




Hello Simon,
I really like how you’ve paired the faded denim with darker colours like navy up top; it helps the black shoes “recede” in the context of overall contrast (whereas something like an oxford shirt in classic white, blue, or stripes-would make them far too conspicuous an element.) Articles like this that explore combinations of smart/casual, texture, colour and contrast are my favorite things to read on PS.
I have full-strap loafers in black and dark brown calfskin, but I feel the style, lack of surface texture, and elongated last might make them challenging to pair with denim – something a bit more casual with a slightly rounder toe more along the lines of Lucas’ vintage horse bits or an Alden LHS would probably be easier. My jeans are also (by necessity) a bit wider-legged to fit my cyclist’s calves and thighs, so that’s a consideration too.


Enjoyed the article and although not directly relayed i realise that despite the love of loafers on the site, i feel very much an outlier as i don’t own a single pair of loafers and haven’t since i was 18. Maybe it’s an age specific thing but as a child of the 70’s/early 80’s i associate loafers with travelling salesman and mods. Penny loafers in particular i find very prissy. Am i on my own?!


Thank you Simon, very useful article! I think Horatio Footwear also does a great job on their Instagram showing styling options for black shoes (mostly loafers).

Kintil Kuntul

Informative and practical guide on how to style black shoes with jeans. Breaks down the often-daunting task of pairing these wardrobe staples effortlessly, providing valuable insights and tips along the way.


I really like all the suggestions, especially the one with the woolen coat. I noticed that even the socks match the entire outfit perfectly.


My Yuketen camp mocs in black chromexel have become a staple item. The pull up is more brown and with brown laces it doesn’t read as flat black which may help their adaptability but I find I can wear them with just about anything casually- black or blue jeans, shorts, etc. I happen to have been wearing them to your NYC pop up last fall where I found the perfect non matching belt to pair- the Rubato brown suede. Dark enough to “go” but not straight black to be too matchy.


Hi Simon, how do you feel about the sockless look with black loafers? Would you consider them too formal or could it work in this context? Thanks!

James Scott

In the photo with the bicycle, what trousers are you wearing please?