You see quite a few bankers around this part of London wearing driving shoes with their suits. They presumably think they’ve stumbled onto a great thing – like loafers, but different, and in a huge range of colours.
But then they can’t see their suit trousers piled up on the rubber nubbins that driving shoes often have on their heels. To those walking behind them, it looks just as bad as wearing chunky trainers with a suit.
Driving shoes and worsted wool (the smooth wool of most suits) are just too far apart on the formality scale. This is why they look wrong together; why suddenly the shoes make suit trousers look flimsy and insubstantial, a little like pyjamas.
Here is my approximation of the sliding scale of formality:
ShoesTrousers
Wholecut Oxfords – Worsted wool
Toecap Oxfords (quarter brogues) – Worsted wool/linen or cotton
Monk-front shoes – Worsted wool
Half-brogues – Worsted wool/linen or cotton
Derbys (Bluchers) – Flannel/worsted/cords or khakis
Smart slip-ons (Norwegian split-toe) – Worsted/cords or khakis
Full brogues (wingtips) – Flannel/cords
Suede/Nubuck – Anything but worsted
Deck shoes – Cords or khakis/jeans
Driving shoes – Khakis/jeans
[Notes: This list does not include boots, extending above the ankle makes any of these types a notch more casual; neither does it include shorts, as I think they can look good with anything but the top three types of shoe; double soles also make any of these a notch more casual, particularly monk-fronts; patent leather should be reserved for formalwear; cotton is the most versatile material and can be hard to pin down, as jeans can go with all but a few of these shoes, as can khakis arguably.]
These, to me, are the types of shoe (beginning with the most formal and ending at the bottom with the most casual) that most suit a material of trouser.
The more formal and elegant a piece of clothing the more delicate its materials and textures are likely to be. Worsted wool needs shoes with sleek shapes, slim soles and clean designs. Heavier wools need heavier shapes, most obviously flannel with brogues. The rough seams and rubber ridges of driving shoes are more suited to jeans or more casual trousers.
Within this range, combinations can work by going up or down one notch, possibly even two. But the problem of wearing driving shoes with worsted is demonstrated – the two are just too far apart.
4 Guest Comments »
1.
Aren’t “Full brogues (wingtips)” more formal than “Smart slip-ons (Norwegian split-toe)”?
Comment by Kai — July 25, 2008 #
2.
So it seems that in terms of ‘practical dressing,’ one might very well build a wardrobe around bluchers as they offer the greatest flexibility up and down the scale.
And actually I’d go even further: I’ve seen bluchers with jeans and they looked great.
Comment by David — July 25, 2008 #
Kai – I would argue that the two are very close, and that full brogues would probably be considered by many to be smarter. However, when it comes to matching textures with trousers, the heavier brogueing of a wing-tip to me is more important.
David – I agree, bluchers are probably the most flexible style there is. They can definitely look good with jeans. Half-brogues are probably the closest rival, though they are harder to pull off with jeans.
Simon
Sadly, those blasted driving shoes have been all over Italy for several years… And many Italian men wear them (though they tend to be younger). They just look stupid with a suit, and you’re absolutely right when you say it ruins the suit by making it look like a pajama.
Guess folks in London got around to copying the look.
IMHO, for all the fame of Italian dress and style, shoes have never really been a strength. We have never really produced a classic style and a quality product on market scale. Some hand-mades are okay, but American and British shoes are the “go to” shoe for a man and his permanent style.
Yes, the Gucci loafer with the metal clasp has a place, but the weejun and its brethren are far superior and less affected. So why bother with the Gucci, or Todd’s?
Initials CG –
Essentially, the problem with the driving shoe is the sole. I wouldn’t have a problem with any upper being worn with a suit necessarily, but those rubber soles, particularly on the heel, just don’t match up. Perhaps some of the driving-shoe manufacturers should offer each style in both a rubber and leather sole?
I agree on the less-affected Weejun as well.
Simon
I think the reason the Italians “get away with it” is the cut of their trousers. They are tailored higher than we wear ours and are often far slimmer and more tapered; so, no puddling on top of the shoe or catching on the nubs at the back.
I think it can work — just not for everyone. And I’d far prefer to see them worn with an odd jacket and trousers.
Good point, EAEL, the cut of the trousers is just as important as the material they are made from.
While the heavier material of cotton trousers will puddle less on the rubber, the cut will also keep them further from the rubber in the first place.
May I ask where in the scale would you put the austerity brogues(wingtip toe cap without any broguing) to?
Would you answer this question? I have been waiting for several days. Thanks
My apologies. I would put them just below cap-toe oxfords.
Thanks for your quick reply. would the austerity brogues go with linen or cotton?
Potentially. They would need to be casual brogues though in terms of colour, and formal cotton/linen trousers in terms of cut and colour
Can you please clarify what you mean by derbys as they can span the whole range of plain, quarter/semi-brogue and wingtips? Does your scale refer to the plain derbys primarily?
If I have a derby shoe, should I approximate its formality by referring to your scale for a derby, or by its brogueing? Thanks
In general, a derby is more casual than an oxford. But you’re right, the broguing etc also affects its formality and needs to be considered.
I would refer to the scale for a derby, but also bear the broguing in mind. A scale with everything taken into consideration (lacing style, broguing, colour, sole thickness, welt width etc) would be rather too complicated
Hi Simon, over the past few years I’ve built up a nice RTW shoe collection (C&J/Cheaney/Church are brands I usually lean towards) compromising of usual Oxfords/Derbys/Brogues and boots of various kinds, but I now want to branch out and try a pair of double monk straps.
It’s not a style of shoe I’m familiar with, but I wonder if monk straps such as the C&J Harrogate or Lowndes are suitable to be worn with dark slim fit denim? My instinct is telling me that the Harrogate is the more casual of the two but I do like the elegance of the thinner ‘City’ sole on the Lowndes.
I really want to try something different that can be worn in a variety of situations smart casual/formal but not sure if the Monk Strap is the way to go?
I do think they can work, but it is a little showy a design – so go for the most subtle and conservative
Thanks Simon, really appreciate your feedback. Enjoyed the article where you discuss your own shoe collection, and interesting to note how adaptable and useful you find your oxfords. Love your Gaziano and Girling loafers. I’ve always considered loafers to be a ‘summer’ shoe. Do you wear these as much in the winter months?
Oh good.
I don’t wear them as much, but I still wear them. As long as it isnt very cold, or wet, they’re fine
Simon, would you say a tassel loafer is quite formal and hence appropriate for a worsted suit?
It’s not that formal, and is just OK with a worsted suit. If the event were quite smart or important, I’d wear an oxford instead
In Your opinion what would a dark brown suede captoe be useful for ?
Flannels
A finer pair of Cotton trousers
Or ?
Lots of things. A casual suit (eg flannel) and most trousers that aren’t smart worsted and are smarter than a chino.
See this post for examples.
Hi Simon
I am interested in your insight about pairing fairly roughened suede brogues and trousers. The link did not quite give the answer.
Between the basic criteria of likeness and contrast I feel the former to make more sense. So seem to endorse a majority of authors. But that narrows down pairing pretty much to flannels IMO (I also feel denim right but cannot quite explain why; maybe roughness too but from a cultural approach, not texture).
What else would you say is good pairing, and why?
Thanks in advance
I think you’re on the right lines with the similarity of texture and casualness Nico, and therefore flannels and things more casual sound like the right choice. Denim, certainly, then casual cotton trousers like canvas chinos, perhaps washed chinos as well?
Hi Simon,
I’ve got question about the formality of a classic penny loafer.
By a “classic penny loafer” I have on my mind one particular model, for example Duke by Edward Green, Hudson by Joseph Cheaney & Sons, Boston by Crockett & Jones. All in black calf, slender, with leather sole, round toe and no decoration.
I’m not from the UK and wonder if this classic loafer is perfectly acceptable for any important business in the City.
I’d think that except for the most formal events (any “tie” event) where a classic oxford is mandatory, this plain penny loafer would be wholly acceptable with dark worsted/mid-heavy flannel suits for all daily business, even if smart and important (banks, corporate boards etc.). Or is this a wrong assumption?
Thank you very much!
J.
Hi John. Yes you’re right, that kind of black loafer would be acceptable for pretty much any business in London. There might be the odd person who would see them as casual, but that’s about it.
If you were concerned at all, a slightly slimmer and longer last might look a little more formal, eg the 184 last from Edward Green rather than the 137 the Duke is on
Hi Simon,
On the formality of shoes, I would say the following is true:
Black is more formal the brown
Oxfords are more formal than derby’s
Less brogueing is more formal then more brogueing (plain toe is more formal then brogues)
Darker is more formal than lighter
Laces are more formal than loafers
Please correct me if I’m wrong on any point.
But if all of this is true would you agree there is a contradiction in the fact that oxfords are more likely to be brogues? It seems to be the case and I personally think that in terms of style, oxford’s are better suited to brogueing with their cleaner lines and (usually) slimmer shape. I find that the open lacing combined with the wingtip makes the design a bit busy.
You’re right on all those points.
But I don’t think there’s a contradiction that brogueing looks better on oxfords. That’s not related to formality. It’s just a question of space for a design to work.
Some people might think, similarly, that a whole-cut is the best thing for black suede, as it looks so elegant and dark/deep. But of course it’s a fairly casual material on a smart shoe.
Formality is usually the most important factor in deciding on shoes like this, but it’s never the only one.
Thanks for the reply, Simon.
I think I meant the contradiction lies in the fact that oxfords are more formal the derby’s and brogueing is less formal, yet brogueing is normally found on oxfords. So, you have the most formal shoe design, barring whole-cuts with the less formal design element of brogueing.
Brogueing on oxfords looking better is just my opinion.
No worries.
Yes, but I wouldn’t say brogueing is very informal, particularly if only a half brogue, and an oxford isn’t necessarily the most formal style, as you say.
It’s no different, really than having a suede oxford rather than a leather one – it’s just taking an oxford down a level in terms of formality.
Thanks for the reply, Simon.
I think I meant the contradiction lies in the fact that oxfords are more formal the derby’s and brogueing is less formal, yet brogueing is normally found on oxfords. So, you have the most formal shoe design, barring whole-cuts with the less formal design element of brogueing.
Brogueing on oxfords looking better is just my opinion.
Cheers
A lovely read! I needed your advice on couple of questions and it would be great if you could help.
1. Can i wear dark brown leather double monk strap shoes with dark indigo slim fit jeans? Do their formality match?
2. I actually do not have a single pair of loafer and was thinking of buying one Simon. Most of the days i am in chinos or jeans and so would ‘leather’ be more appropriate or ‘suede’?
1. No, not really. The monk style is quite smart, as is them being leather
2. Suede probably
Thank you so much Simon!
Would leather penny loafers go with jeans or do you consider it as smart as a leather monk strap?
Not as smart, and they could go, but suede would be safer and more versatile
Thanks Simon!
One last question if i may ask.
Do you have any other ‘leather shoe style other than leather sneakers’ in mind which would go with jeans or would leather loafers be the maximum you would go with jeans?
Loafers or boots probably
Simon i have A couple questions. I buy my second pair of leather dress shoe. After black cap toe oxfords i buy mid brown(burnished) derbys. Because i hate brugging and love more “sleek” style they are plain cap toe. Can i match them with my dark wash denim ? Indigo and very dark blue. Also if They work with medium blue jeans colour.? All my jeans are straight slim and tailoring for my person. I want buy derbys with ligter colour of bronze but the contrast with dark denim was to big for me even i like sonetimes wear white sneaker with black denim. Mid brown looks more versatility i think. Sorry for my english, greetings from Poland.
Hi Lukas,
Mid-brown leather can be OK with denim, but if the jeans are very dark it might not work that well. You’d be much better off with brown suede in that regard.
A pale brown can look great with denim too, but suede you will find more versatile.
I hope that’s helpful
Hi Simon,
I was wondering if black half and quarter brogued oxfords would work with medium to dark wash denim and if not, what would you recommend that has a similar style if possible?
No, I wouldn’t wear any oxfords with denim really. I’d want to wear a suede loafer with something like that, or a leather loafer at the most
Do oxfords also not work with beige chinos that are in the same style as jeans?
I don’t think so, no
Thank you for your response.
I imagine that black calf loafers would work from jeans to charcoal wool twill pants along side a black leather biker jacket all the way up to a navy blazer. Am I correct in my statement?
Also, what would be an equivalent for winter when it is cold and wet?
I think you’ve asked this question again lower down?
What style of loafers would you recommend that can be dressed down to black leather biker jacket with jeans all the way up to a navy blazer and charcoal wool twill pants?
I’m not sure anything can go that far. I’d wear boots or canvas trainers with a biker jacket as well.
But at a push, perhaps Color 8 cordovan loafers
Would dark brown suede derby or brogues go with dark denim?
Yes they should do. If in doubt, go with derbies not oxfords
Simon! May I ask two questions regarding shoes.
1) Can I wear dark brown suede driving loafers with navy chinos?
2) Would dark brown suede derby shoes look good with button down Oxford and dark denim?
1) I wouldn’t wear driving shoes outside at all, personally. It’s an odd look – the shoes look very chunky and not that elegant. And they wear down quickly.
But yes, dark-brown loafers are fine with navy chinos.
2) Yes
Hi Simon, between black cap toe oxford – rubber sole and black single leather derby – leather sole, which would you say it’s more formal?
Many thanks,
Jack
Probably the Oxford. The sole doesn’t get noticed as much
Thanks, I am actually considering investing in a cap toe oxford between Edward Green’s Chelsea 202 and Crockett and Jones’s Audley from hand grade collection.
I assume Edward Green would have better quality in terms of price (£345 more expensive), as I remember you mentioned ‘you get what you pay’ regarding Northhampton’s shoes. However, it would be really helpful for my decision if you could expand a bit more on their difference in terms of value for investment.
Many thanks,
Jack
Yes, that’s broadly right Jack. The difference will be mostly in materials – the leather used for the upper, the lining and so on, which will polish better and look better over the years. There will also be some small places where the finishing might be better.
Thanks, Simon.
Hello Simon, if I mostly wear dress cotton chinos, wool fresco, wool flannels, what would you recommend between brown suede and calf leather?
Also, would the double monk strap fall into that category level of formality?
Many thanks,
Jack
Both would work Jack, I’d go on which you prefer.
A double monk would work, but they are a bit flash, and haven’t been trendy for years. I’d avoid them if you don’t have a large shoe collection
Thanks, Simon. If I choose a suede cap-toe oxford rather than calf leather, I assume it won’t fit into the formal suit, am I correct?
Also, if it is brown suede with a rubber sole for the double monk strap, do you think it would work with mid-blue jeans? For a more casual weekend look?
Yes that’s right on the oxford.
Yes that would be right on the monk too, just with my caveats above
Thanks, I may be wrong, but I haven’t seen you wearing brown suede shoes in cap-toe oxford but rather in loafers, chukka and split toes. If I observed it right, is that because you believe cap-toe oxford looks and works better on calf leather?
No, I do have a pair, even if I wear them a little less. See here
Hi Simon,
I regularly wear sports jackets and dress pants. For this purpose, I’ve been trying to decide if my toecap oxfords or derby shoes would be more appropriate. I feel both can be used in the instance I’ve described, but for my purposes, is one more suited to my outfits than another?
Thanks!
Probably the derby, Dean, that would be the classic choice. However, it does also depend on many other factors – the problem with these kinds of questions and rules is they oversimplify.
For example, the toecap oxfords will look much better with a navy jacket and grey trousers, than a brown tweed jacket and tan cav twill trousers.
And if the oxford is brown suede, in a rounded last, with a thicker sole, it will look a lot more casual than a black calf on a long last with a thin sole and bevelled waist.
Does that make sense? Just bear all these things in mind, then look at the outfit and consider whether you think the shoes look too smart or casual
Hi Simon,
Would you be able to get away with wearing sharp full brogues (wingtips) with a high twist woolen trouser, due to the texture of the wool? Or is it best to stick with half/quarter brogue for a high twist match if you enjoy broguing?
That would be fine. With all these things, remember it’s just something to bear in mind – the relative formality and informality of things. It should build into how you think about outfits, not drive them. Small differences between one category and another are not the most important thing
Which toe shapes are most appropriate for morning dress and business suiting?
Subtle, understated. Usually round, not too elongated