edward green falkirk wingtip
Edward Green Falkirk – casual, in its wingtip layers and punching

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:


Wholecut OxfordsWorsted 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 shoesKhakis/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.

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initials CG

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?

Easy and Elegant Life

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.


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


Thanks for your quick reply. would the austerity brogues go with linen or cotton?

Kevin Lee

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


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?


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?


Simon, would you say a tassel loafer is quite formal and hence appropriate for a worsted suit?


In Your opinion what would a dark brown suede captoe be useful for ?
A finer pair of Cotton trousers
Or ?


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


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!



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.


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.


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.



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’?


Thank you so much Simon!
Would leather penny loafers go with jeans or do you consider it as smart as a leather monk strap?


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?


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 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?


Do oxfords also not work with beige chinos that are in the same style as jeans?


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?


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?


Would dark brown suede derby or brogues go with dark denim?


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?


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,


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,


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,


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?


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?


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?



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?


Which toe shapes are most appropriate for morning dress and business suiting?


I’ve recently been on the hunt for a pair of smart-but-casual shoes that I can wear with light wash jeans, chinos, grey flannels and the like.

Permanent Style is very loafer heavy (and I can understand why), but I’ve recently given up on trying to find some that fit me (very sadly).

I’ve turned to suede derbys, bluchers and the like instead.

However, I’m struggling to get over the idea that smarter lace ups just look out of place with casual trousers.

They just feel so long! Reminds me a bit of the boys who would wear school shoes with jeans on own clothes day…

Any tips / recommendations for getting smarter lace ups that work with jeans? Or any pairs you’ve had success with?

The best I’ve found is the Paraboot Avignon in suede, but the visible green tag makes them a little bit too casual/flashy for work.


Totally, and I hadn’t actually seen the Alden’s before but they do definitely look more appropriate than something from Edward Green, for example.

But I don’t know, there’s something about it that I’m not confident I’d pull off. Maybe just a hang up I need to get over. I’ve seen a few shots of you in split toes with jeans and thought they look good.

I do tend to wear light wash jeans as well, which could be part of it, I guess, given they themselves feel like the most casual kind of denim.