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As the last post on building a wardrobe - focused on Neapolitan tailoring - proved popular, I thought I'd do a second looking at shoes.

But rather than look at my whole shoe collection, which numbers more than 40 pairs and would take a long time to go through, it seemed more effective to focus on bespoke shoes.

The bespoke set is both more consistent and reflects many of themes in the wider collection.

As with the first post, the focus here is on style and building up a functional, versatile wardrobe - rather than comparing the makers.


GJ Cleverley bespoke brown oxfords waxed laces

Cleverley dark-brown oxfords

November 2010


The first thing to note about my commissioning of bespoke shoes is that it is boring. Or to put it in a positive light - practical and consistent. 

My first pair, from Cleverley, is a case in point.

The colour is very-dark brown. The kind of brown that goes with every suit from charcoal to tan. For anyone buying a pair of formal shoes, I highly recommend it.

I also recommend oxfords as a starting point if you wear formal clothing at all. It is more formal than a derby and goes with anything up to chinos and jeans. 

Having said that, the shape of the Cleverleys - with their 'Anthony Cleverley' elongated toe, makes them more formal than most oxfords, and I wouldn't wear them with most casual trousers as a result. 


Cleverley black bespoke brogues

Cleverley black imitation-brogues

July 2011


The second pair were black. This also felt practical, although as you will note down the list, they became my only pair of black bespoke shoes. 

Although black is great to have for the most formal or conservative of occasions - a lawyer's office, an evening event - shades of brown are always more useful outside of that. 

Brown is also more interesting to polish. A touch of black to the toe, perhaps even around the heel, and it can gain a lovely range of tones. Black, by contrast, is rather dull - all you can do is make it shiny. 

Which is one reason why British shoemakers have never been great at colour and patination. 


gaziano and girling bespoke loafer

Gaziano & Girling seamless light-brown loafers

June 2013


The collection so far lacked anything resembling a casual shoe, and so my next commission was a loafer.

And, in terms of shades of brown, we could call this a light brown (not tan). Inappropriate with a navy or charcoal suit in terms of its colour - and most suits in terms of its style - but excellent with everything else.

Together with the next on the list, this has become my most useful shoe.

The only thing it lacks is a casualness that would have come from a more rounded toe and less elongated shape.

This is worth noting closely, as it applies to suits just as much as shoes - the more stylised, elongated, drawn out the shape of a piece of clothing, the less it is suited to casual wear.

That's why pretty much any Alden shoe will be more casual than a G&G shoe. 



Gaziano & Girling mid-brown adelaides

March 2014


These adelaide oxfords ('adelaide' refers to the line of the section around the laces) were originally made in tan by mistake. 

They were meant to be mid-brown. Somewhere between the dark-brown Cleverleys and the light-brown loafers, and for me the most useful colour of all. 

When I travel, as an illustration, I will always take one pair of dark-brown shoes and one pair of mid-brown, no matter what else there is. That covers most eventualities. 

(And it's usually three pairs as a minimum - you should obviously rotate every day if you can, and if one starts to cause you pain for some unknown reason, you don't want to be left with just one pair...)

The adelaides were patinated by G&G for me - to turn them from tan into this mid-brown - and to give some nice variation of colour in the toe and heel.

They have become probably my favourite pair of shoes.


Stefano Bemer bespoke shoes and cream gabardine trousers

Stefano Bemer tan oxfords

July 2014


OK, so now it was time for tan. All other shades of brown had been covered. (They are slightly lighter than photographs suggest.)

Again, it was an oxford, to maximise its versatility with most of what I wear (suits and sports jackets/trousers most of the week - certainly all the working week).

And it had a slightly thicker sole than, for example, the Cleverleys, to help it be that little bit more casual. That also tends to be the Stefano Bemer style. 

I have to say, I love tan shoes and I can completely understand why so many guys want to wear them with navy suits, with grey suits, with everything. There is a lovely richness to the colour and they are great to play with polish on. 

But the rule of thumb that a shoe should be darker than the trouser it is worn with remains a good guide. Certainly, tan with navy is too far.


Tim Little bespoke boot chelsea sole

Tim Little tan chelsea boots

October 2014


Interestingly, as with the Neapolitan jackets wardrobe piece, there would appear to be few mistakes in this series of commissions. 

But these tan boots certainly fall into that category.

The appeal of tan had a role to play, and there is always something attractive about the amount of leather involved in a boot as opposed to a plain shoe. I also had a teenage association with chelsea boots. 

But these have not seen much wear.

I rarely wear boots during the week, as they will become too hot in an air-conditioned office. And at the weekend I tend to prefer a suede shoe, a split-toe shoe or my Common Projects

There is also, I have to say, something about a chelsea boot that I find I don't like in practice. It is to do with that same uninterrupted volume of leather at the bottom of a trouser leg, which has a touch of the dandy about it.

I will have them patinated to a dark brown at some point, however, and see if that appeals more. 



Cleverley Russian-reindeer double monks

December 2014


If there is an overarching theme to this post, it is of realising - again and again - the virtues of being boring. 

For me, this applies to shoes in particular because I generally prefer to experiment with tailoring rather than shirts, shoes or accessories.

My shirts are largely pale-blue, my ties mostly dark, and my shoes dark brown. It makes it a lot easier to wear toabacco linen or green flannel. 

So here, with these beautiful Russian-reindeer double monks, I should have gone with an oxford. 

I do like monk-front shoes. My first ever pair of good shoes was a single-monk Oundle from Edward Green, and I am very fond of them. 

These Cleverleys were also beautifully executed, with the antiqued brass buckles and hatchgrain of the Russian reindeer. 

But they would have been more frequently worn, and taken travelling, if they had been oxfords like my Stefano Bemers.


santoni fatto a mano su misura2

Santoni dark-brown derbys

July 2015


The next commission, at Santoni, learnt from that lesson. 

Although derbys (the first bespoke pair) the colour was that super-versatile mid-brown of my G&Gs and they have proved very useful as a result. 

The high shine and patina makes them a little less casual, but the derby construction is arguably more important. Great with dark-green cotton trousers, as shown. 


Foster & Son bespoke shoe london

Foster & Son dark-brown oxfords

April 2016


Readers will be familiar with the issues I had with my Foster's in terms of the finish - which was patinated to a dark brown but quickly came off. 

The mid-brown it was replaced with was much better in terms of consistency, but lacked the variation in colour, largely as a result of it being an aniline leather. 

It is a conservative oxford in other respects, although also not the best fitting of the bespoke shoes I have had, and so they are used largely as a back up.

(Having said that there is plenty of toe space, which is the area I most commonly get pain if I'm on my feet all day. So they can be useful for travelling.)


Saint Crispin's  personal last shoes

Saint Crispin's croc wingtips

May 2016


Picking this design as my first pair of Saint Crispin's was a good compromise. 

Although they are best described as a mid-brown, it is a rather greyed brown that is a little unusual (one of the benefits of Saint Crispin's dyeing their own uncoloured leathers). 

And of course there is the crocodile around the laces. Altogether it makes for a shoe that is just about as unusual as I can wear with most things. 

I should mention that I also keep three or four pairs in the office, as I cycle to work most days and change when I arrive.

This is another reason for versatility - and the SCs just about qualify for inclusion. 


Stefano Bemer bespoke suede oxford

Stefano Bemer tobacco-suede oxfords

July 2016


Suede! The one material clearly missing from my bespoke collection thus far. 

In the past year I have found I wear suits less during the week, and more of those Neapolitan jackets. This has created a focus on more casual shoes, such as suede, and less on long-toe Cleverleys.

Controversially for me, I went with a light-brown tobacco suede rather than dark brown, and they have had less wear as a result.

But they were beautifully made - as I reported at the time, my best fit yet - and are a pleasure to have in the collection. 

Indeed, there is a point here about wardrobe building that we haven't touched on yet.

When you're investing in clothing for the first time, it makes sense to start conservative.

It's hard to do (I splurged on a pair of calf/suede Corthays as my first very expensive shoe!) but is more rewarding. Start with something you know you'll get a lot of use out of, and build up.

Tobacco-suede shoes are a much more sensible buy as your eighth pair of shoes than as your first. 



Saint Crispin's brown-suede chukka boots

December 2016


Finally, most recently, my chukka boots from Saint Crispin's. I'm including SC in this list of bespoke, by the way, as both pairs involved an amended last and a hand-sewn welt. 

These boots have proven a very good choice.

My feet don't get as hot - not being a full-height boot - and they are dark and smart enough to be worn in the office with some outfits. 

In fact, in some ways these chukkas are a perfect illustration of my preferred, always subtle, style.

They are, at first glance, merely a dark-brown boot, and if worn at the weekend with chinos or jeans, get few second glances.

But the curved shape of the quarters, the two-lace fastening, and of course the hand-cut waist that curves in beautifully underneath, elevate it in a very subtle way.

Rather like the best bespoke tailoring, most people would say they thought they looked great, but would struggle to put their finger on why.


Gaziano & Girling fitting bespoke suede slip-ons copy

There are other bespoke shoes in the works, of course, which pushes this collection out more prospectively. 

Continuing the suede theme, there are some brown-suede slip-ons being made at G&G (above). Norman Vilalta and I have been working on a boot project that has taken (a very enjoyable) five sessions in two years. And I have just commissioned a pair from Stivaleria Savoia in Milan. 

They are dark-brown oxfords.


Photography: Jamie Ferguson, Horst Friedrichs, Luke Carby, Jack Lawson and myself. 

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Adam Jones

Although I have not built my shoe collection on Bespoke pairs I have been doing it with high end MTO and RTW, replacing many of my old Crocketts etc. The hard thing is always picking something conservative over something you love. My First Pair of G&G’s was a Navy wholecut oxford and my second a tan spectator.. shoes I adore, but wear twice per year. I have added more sensible items since then, brown brogues, adelaides etc Its always a tug of war between love and practicality.

I still have not learned my lesson. Last year I got a polo suede tassel loafer, lovely shoe but so hard to wear day to day, and too formal to wear easily and casually on holiday.

Don Ferrando

A very nice colection of shoes.
Which pair of them – if any at all – would you wear with you ES grey flannel suit?

A. Keller

I noticed that Bordeaux/burgundy/etc. is absent from your collection. Is there a reason for this or just a matter of taste? As for me, I have a pair of imitation brogues (oxfords), with a nice patina in those tonalities, that are among my favorite pairs. I find that they go well with blue suits/trousers, with jeans, and even with certain shades of brown.


do you think burgundy shoes match very dark green and dark brown flannel trousers?

Matt S

I find that burgundy shoes can go very well with grey suits too, just as Cary Grant wore burgundy shoes with his grey suit in North By Northwest. Pairing them with certain browns is what I find most challenging.


Along this spectrum, I have a pair of shoes with a definite purple cast (Vass plum museum balmorals). I think the blue tones allow it to sit more quietly alongside most trouser colors, while still being a bit unusual.


Simon, have you noticed that the colour you find most useful (very dark brown) also tends to be the least commonly available rtw – at least in London shoe shops? To me it seems to be mainly a case of black or mid brown throughout the rtw market – do you have any suggestions of where to find this colour by any chance?


Good point. I have been looking recently for a dark brown derby. Very difficult to find in a plain calf which is a shame given, as Simon points out its versatility with a variety of colours, tones etc. I did see some in the Cleverley shop but like many others you see they were a very ‘chunky’, country style of shoe; great for some contexts but not particularly elegant.


Sam, try Crockett & Jones for some very dark brown RTW styles. I recently purchased their ‘Teign’ dark brown suede loafers from the store in Royal Exchange. The shoes are excellent and the staff were extremely helpful.

Kev Fidler

Firstly, my apologies for previously appearing as ‘Anonymous’. I agree fully with comment re C&J at Royal Exchange. Excellent service (they remembered me from 6 months previously). Also I agree there is good dark brown suede available but not a lot of that deep tone in plain calf. Some cordovan covers it but is often burgundy.


Tim Little has a lovely walnut oxford that is a darker brown. Lovely variation in tone too.


Thank you for this great article, Simon! This is alctually a good guide for a novice like me on how to select shoes according to their usefulness. I understand that you here are talking about bespoke shoes, but would you mind on commenting about different approaches to get started in the well made shoe game (by that I mean switching from glued shoes to sewn shoes)? I my case, I could set aside a small montly budget (about 150 GBP) solely for shoes, but should I start with the entry level goodyear-welted shoes (like, Carlos Santos, Carmina, Meermin), or would you advice to save up a bit for the medium level shoes (Crockett&Jones, Enzo Bonafe) and then aim for the top level a bit later? Any advice from other readers would be appreciated as well. thanks!


Thank you Simon! There is a decent rotation of shoes at the moment (but mostly for amount, not quality). Could possibly recommend some shoemakers in the mid-market i should definitely take a look at? (as I understood from one of your older posts, it is better to spend some time to compare the fit or multiple makers).




Hi Justin,
This is a very sensible plan. In your … shoes, as it were, I would start by taking a look at Bodiley’s London Collection and Alfred Sargent (A Fine Pair of Shoes could be a retailer to consider).
Bear in mind, though, that your biggest challenge at this stage actually is to know exactly the MOST VERSATILE shoes you would need (styles, colors and suitability to weather).
I guess that Black oxfords shouldn’t be your first pair of shoes.


Thank you both, Simon and John, for your sugestions! I will take a look at the mentioned schoemakers. C&J Handgrade looks very promising at the moment, but will also look at the other two. My problem, however is, that all my business trips are either in Germany, Austria and Switzerland, therefore I hope I can find something there to try on, as we dont have anything like this in the Baltics (at least as far as I know).


Did not want to by anonymous here, sorry


I would have one follow-up question regarding C&J handgrade shoes. I price was not an issue, what would be the key differences between C&J handgrade and Edward Green shoes? Is there such a big diffeerence as the price for RTW states? thanks!



Further to Justin’s comment, what are your views on the likes of Meermin Mallorca, Carlos Santos, etc? Not as good as C&J, presumably, on the basis of your response – but would you say that they represent less good value, even taking into account that they’re normally a fair bit cheaper?

While articles on bespoke shoes like this are interesting, I often find them somewhat academic (inasmuch as I am unlikely to be able to justify buying bespoke shoes from the likes of G&G, Cleverly, et al, on many occasions in the future, near or distant). More coverage of the lower end of the market would, I would have thought, be quite useful for a lot of your readers. Or are all 481,999 of your other readers buying bespoke?!


Felix vL

I have a pair of Churches and a pair of Carlos Santos, and I must say I much prefer the latter. Would definitely buy again.


If you had to chose one shoemaker, which would you chose? If you need criteria, best value for money.


This may appear to some as an odd question and is certainly a little off topic but one I feel I must ask. How do you all deal with the issue of leather soles in the rain? Perhaps it is just me but even with light rain certain pavements turn into an ice rink. Ive always thought it may be to do with my walking style but and have always wanted to ask if others also suffer. Any responses would be appreciated. Thanks


Alex, I definitely have the same experience. A lot of people on menswear forums (fora?) swear by SWIMS, which are a kind of rubber bootie you put around your shoes. They certainly keep your shoes dry but I always felt it was a bit of a hassle putting them on and taking them off all the time (and you feel a bit silly doing it in public!)

My solution has been to get shoes made with a thin rubber sole. You need to get them properly soled vs. the hack job most cobblers will do that involves glueing a strip of rubber onto regular leather soles. EG, Vass and Saint Crispin all offer this type of sole MTO and I think it works on all but the most delicate styles (although some iGents seem to hate them on principle!)

Matt S

The Santoni brown derbys are one of my favourites here. Three-eyelet derbys are very comfortable, and I find that they pair well with suits as well as casual clothes. The detailing on yours gives them a more casual look, but with the right balance I think they can work well with almost anything.

I also have to say I wish there were a better selection of ready-to-wear shoes in dark brown. Everything these days is light brown or tan, and it’s common to see these shoes poorly paired with navy suits.


What a fantastic collection of shoes, I’m very jealous! Couple of thoughts:

1. I’m surprised you don’t get much use out of the chelsea boots. I can see how they might not work with more formal outfits but wouldn’t they look great with well-worn denim and a chunky sweater at the weekend?

2. I know I’ve mentioned this before but I still can’t fathom how you manage with so few rubber-soled shoes. I probably need them 70% of the time during the winter months and it rains much less here in NYC than in London! (I did try using SWIMS but it felt a bit precious putting them on every time I wanted to go outside!)

3. Those reindeer monks are stunning. They would definitely be my most worn shoe if I had a pair…


Some beauties and some shockers. It may just be the photos but some look like they are from a period dressing up box. The SCs are scary.

You miss some classics too. No tasseled loafers?

Matt S

I’m with you on rubber soles. NYC’s frequent and heavy precipitation demands that I often resole with Dainite or add rubber half soles over my leather soles. NYC is actually much rainier than London, though London is cloudier and gives a drearier impression. London has a lot of light rain, while NYC gets more rainstorms and snowstorms. Because of this, leather soles can work much better in London than in New York on a regular basis.


Matt, you’re absolutely right (I even checked the MET office website to be sure!) That said – at the risk of getting us way off the far more important topic of fine quality menswear – even though NYC gets more rain in terms of inches per year, both cities have almost the same number of rainy days (106 and 122 to be precise) so it definitely seems like there’s still a need for more rain suitable footwear. Agreed it could be an interesting separate post…


Interesting, hope I’ll be able to upgrade to bespoke one day. I recently bought some lovely tan brogues from Cleverley in their sale – 250 quid, quite a bargain I think. However, to be honest, they killed my feet, a problem I have had before with high end footware. They were definitely the right size, I was measured before I bought them, and I wore them at least a dozen times, but was on the point of writing them off when, as a last resort, I took them to my friendly neighbourhood cobbler, who subjected them to steam treatment and stretched them slightly at the points of chafing. They look no different and are now perfectly wearable. I’d recommend this to people with fit issues who aren’t in the bespoke league.


I understand the issue of conservative commissioning (of laced shoes; seven Oxfords, one Derby) but there seems to be a good deal of repitition (esp. brown of shoes). It would be similar to commissioning many blue suits. Some budapesters, norwegians, bluchers, saddles, woven, balmorals etc. (…OK maybe not the saddles) would be welcome and add some dynamic flair to the range. In terms of building a shoe wardrobe variation is key (given the relative limitations in overall styles). I think wholecut (oxford), toe cap (oxford), wingtip brogue (oxford or derby), plain toe (derby) and monkstrap shoes in black, brown, tan or suede are key and supplemented by horsebit, moccasin, penny and slipper loafer styles. For the great outdoors chukka, chelsea, wingtip and officer style boots might complete the collection whilst remaining elegant.

l d t

Simon – No mention (not so much as honorable mention) of sneakers/trainers in your collection. Are they separate and apart from the 40+ “shoe” count, i.e. do you consider them shoes?


Hi Simon,
You didn’t mention the dark brown suede loafers made by Stefano Bemer, which I personally find very very appealing!
Yet I’m flabergasted at the sheer number of your shoe wardrobe! Way too much! Recently, I’ve read a post by someone who boasted having … 60 pairs of shoes! Frankly, whereabouts are you guys going with those shoes!
I really believe in the soundness of Michael Drake’s philosophy with respect to shoes too. Indeed, VERY WELL crafted GY shoes, even the RTW ones, could last years, if properly taken care of. And above all, they age beautifully! So frankly, I don’t see the point of having, say, 12 loafers!
Unless one is interested in building up a shoe collection like the one Imelda Marcos had.


Hi Simon

I agree with your reasons for creating the above collection, but why no split toe such as the EG Dover? I always thought that it was a very versatile shoe especially when worn with neapolitan jackets and for bridging the casual/formal outfits.


Split toe shoes have to be one of the ugliest things in existence…


For the most part I agree with you, although I do rather like the Edward Green Dover…


Well, G&G Hove comes pretty low on my list of ugly things


Simon- I really enjoyed reading your piece. Reading your blog has been an important guide in starting my show collection. I have very recently commissioned my first pair, a dark brown oxford from Bestetti. For my second commission I am leaning towards a black oxford from George Cleverly using their elongated toe style during their trunk show to Singapore. What would your advise be on style, sole, material, patina and finish. Anything specific to Cleverly you would advise? Also, would you advise getting initials on the sole on such a pair of shoes?
Thanks- KB


So what are you supposed to wear Tan shoes with if not Blue or Grey? I love the look they give with those color pants but I can see what you are saying.

Bobby B.

I disagree that Oxford shoes are for chinos and jeans, they certainly are not! That is what derby’s are for, as well as odd jackets and trousers.

Adam Jones

Like with anything there is a wrong way and a right way. Highly polished cap toe (like the Cleverley’s above) are not going to go with your stonewashed denims (not that it doesn’t stop people doing it) But a brown brogue, or even the Bemer oxfords above would certainly go with dark dressier jeans and well fitting Chinos.


Simon, I wrote the comment re. variety (budapesters), your response was interesting and not one I had considered (the key being greater variation of other elements). Expanding on this do you therefore see elegant shoes as an anchor to an ensemble (vs. something that brings its own attention). If so how do you see the choice of shoe supplementing the variable aspects (tie, hank, shirt), conversly, do you see them as a background element not included in this consideration?


Simon- could you please advise what colour/material one should go with for their first loafers in their collection? Would you recommend any of the makers for penny loafers with an elongated toe. In the warmer climates in Asia I tend to wear the loafers to work a lot with chinos and sometimes with a suit. How would you suggest loafers be used in combination with clothes? Are they strictly casual and don’t belong with a suit?



I looked at your collection above, and found all the shoes that appealed the most, had one thing in common – they did not have those little holes (especially on the toe) that for me – detract from a clean design..

I have somewhere north of 30 pairs (but that includes cycling shoes, etc., ) and the only ones that have holes are athletic..(for breathing, I suppose).

I forget, what are they called again, and why are they still around? (on dress shoes that is.)

Your Santoni, and Foster and Son shoes provide a great contrast to the St. Crispin’s …so much simpler a statement…

The holes to me are a hallmark of the most obnoxious office shoes offered by mid-level American brands…The slip-ons with tassels, a tongue, wing-tip details, all topped of with a myriad of holes on every surface..They could pass for golf shoes if they were white, and had cleats….

Best(?) exemplified by :


or even better with an additional strap :


Nicolas Stromback

Hi Simon!

An aspect of buying shoes that is not covered in this article is the issue of what sole to go for. I understand that this may in general be relative to where in the world one lives; an italian most likely would not go for rubber soles given their climate, whereas we in Sweden have some of the most demanding climate for shoes.

I myself have both leather and rubber soles but find that Im leaning more towards rubber soles for those high end shoe purchases so as to not ruin the shoe should weather hit us.

How do you approach this? Maybe this is grounds for a whole new article 🙂



Simon, the odds of you not having answered this question before is close to zero, but since I could not find it maybe you can still give me a brief hint: How come in all your excellent articles on shoes I never seem to come across a note on cordovan? Is there some hidden terrible thing about those we should be mindful of?

D. Thompson

Simon great article. A few points though: 1. my understanding from those on Styleforum more educated than me on the point is that monk shoes are a variant of Derby shoes. That would sit the Cleverley Russians into the Derby category. 2. I note that you write in the shoe review that your Foster shoe had the best fit of any first bespoke shoe… that is lost in your article above. 3. Related to 2 above, I note from Foster that they have changed their patination program (and that in his review Will B. of asuitablewardrobe thought Foster did colour very well). Do you revisit makers for responses to any criticism you may legitimately have? That might help the reader better assess a product and means the maker too benefits from your review. 4. Given the rise in visibility on the internet of Japanese makers, do you have plans to review the likes of Messrs Fukuda, Suzuki, Ann bespoke, etc? 5. Any plans to cover the London use of out workers and compare with in- house production models? 6. St Crispin categorised as a bespoke is controversial. Does a modified standard last plus a hand welt make a bespoke or should a bespoke shoe start with a bespoke last cut from virgin block or smaller last shaped block and whittled down? This is the classic last with fit modifications, no? I should be grateful for your thoughts. DT


Thanks Simon. I have seen the Japanese coverage, but meant a full product review, including a commission. I take your point regarding outworkers, but I disagree. I think that there can be a palpable difference in the input of different outworkers. Thanks for your clarification regarding St Crispins and whether you consider them to be bespoke. As to the next poster’s point on bespoke shoes: “I find absolutely no sartorial or qualitative advantage in bespoke shoes when compared to the high end RTW brands”, I too have bespoke and MTO and RTW shoes and note that even though my foot is easy to fit, the bespoke shoes fit better in that they hold better around the heel and instep than MTO/RTW. Further, the shape that can be achieved in bespoke seems far better (again subjective) with bespoke… I think due to the high level of handwork in the hand welting etc. I don’t think the difference is as noticeable as with a good bespoke suit, but I do think from close range the difference in shape that can be achieved is clear. DT


Doubtless posters in this hallowed cyber style hall will have very different financial means and happily folk can spend their hard earned wonga as they like.
That said, unless somebody has difficult feat that can not find comfort in RTW, I find absolutely no sartorial or qualitative advantage in bespoke shoes when compared to the high end RTW brands and I say that as the proud descendent of cobblers and tailors.
For a third or for a maximum of half the price of bespoke, you can find the equal in RTW and put the balance towards a bespoke suit or coat where the advantages are omnipresent.
Excluding summer casuals, I have 3 pairs of high end RTW shoes and 2 pairs of boots that can handle any sartorial challenge thrown at them and they are all incredibly comfortable.


Fully agree.

Crockett make a great shoe, and there is little to differentiate in quality frankly with a bespoke apart from a nice warm feeling. Get real Simon. Compare their Edgware or Monkton with one of your bespoke alternatives and try to justify the price difference please.

Reuven Lax

Although compared to St. Crispins the aesthetic differences seem more minute. My Crispins have a fine welt and a beautiful waist. While there are a few minor areas where I suspect bespoke shoes would fit better, they are indeed fairly minor. For someone without difficult fit issues, St. Crispins do seem to provide many of the aesthetic benefits of bespoke shoes.


I can’t agree with this one Simon.
Some years ago I was seduced by either Olga or her patina, I can’t remember which, and commissioned a pair of bespoke Burluti’s. They arrived as if fitted by the Gestapo and I went through a level of pain akin to self harm trying to wear them in.
The added value qualitatively or quantatively just isn’t there versus the likes of RTW Crockett, Lobb and the like and I’m afraid your own photos support this point.

Richard Jones

Lovely collection Simon. Are you just polishing the heel + toe in ‘black’, or the whole shoe on your G&G Adelaides? These have always been my personal favourite from your wardrobe / collection. I hope on Saturday when putting together your outfit you consider wearing these – would love to see them in person.

Good luck!


Hello, may I ask if the quality of Saint Crispin’s leather is good? I have heard quite negative reviews on the choice of their leather. Thanks!

Mike Yates

Hi Simon
What are your thoughts on Fosters RTW line?


Simon- I notice you have not used Bestetti. Is it because you don’t like the style or because smaller shoe makers such as Bestetti don’t get the quality say a Cleverly or a Stefano Bemer usually get? Because Bestetti definitely prices in over say a Crispins that you clearly admire for quality.

Ahmed Bashir

this SCs with the croc laces … next level!


Very nice collection. Wish I could afford it. I´m also building up a shoe wardrobe, but based on english RTW or MTO, since that´s as far as my budget stretches.

Regarding the MTO´s, I have a question. They are handmade by a reputable maker, and while I do like the general results and finishing, both pairs have notable imbalances between the left and right shoe. In one case, the toe caps on the right and left shoes have different length, and slightly different shapes. On the other pair, the aprons have different shapes. On the left shoe, the apron is pointing more to the outer side of the shoe, and on the right shoe the apron generally follows the shape of the sole. Again, the differences are not large in actual millimeters, and difficult to measure, but it does create a visual imbalance when looking on the shoes from above. How large differences between the shoes do you find acceptable, and when is it a question to discuss with the maker?

Generally this question also comes up with MTO clothing, but there alterations may be possible. How large differences to the ordered/expected measurements are acceptable?



Simon, I have been reading your blog for several years and this post in particular has raised a question. I am planning on purchasing either a pair of Allen Edmonds 5th Avenue Captoes or Allen Edmonds Warwick Monk Straps. They are built on similar lasts and each fits my foot well. I am looking at both shoes in similar Dark Brown shades. Thank you for all the work that has gone into this blog, and I look forward to what you have in store for the future.


Hi Simon,

One of the issues I have with my leather-soled shoes is that the toe area gets worn a lot faster than the rest of the sole, which leads to an earlier than needed resoling. I’ve seen that some people use metal toe tabs (sometimes referred to as lulus). Both C&J and EG install them. What is your opinion of this solution? Have you ever gotten it done?


Simon – can you recommend any London shoe shops that carry a good stock of various English made shoes? I’m not in a position currently to go bespoke but would like to get a well-made pair of shoes such as Crockett & Jones but ideally would like to be able to view and try several brands under one roof.


Hi Simon

Would you ever wear leather loafers in winter? Or is autumn the latest time to wear loafers?


Hello, may I ask what outfits may work with blue shoes? This color seems to be a popular option for bespoke shoes, but I can’t think of any suit color to match with. Thanks!

Andrew Walker

Thanks for this Simon.
On re- reading the article and the comments it occurred to me there was little discussion of wingtips generally (save your AC croc wingtips and one comment). Are they a useful addition in a dark brown leather with broguing, or are they a confused or dated shoe do you think? As context, I tend to wear navy or grey flannels with a jacket in grey, navy or brown. Thanks in advance.

Andrew Walker

Thank you Simon,
Best wishes


Happy New Year Simon!

I have long struggled to find shoes that fit me well–my heel is disproportionately narrower than the forefoot, so I’ve never found an RTW brand that works. I’ve decided, therefore, that going bespoke is probably worthwhile for me. I’m also not one who wishes to have a large shoe collection–a small, versatile collection is all I’d like.

The only major centre I can reasonably travel to frequently for fittings is Toronto, Canada. It appears my options are George Cleverly (seems to visit maybe 3 times a year) as well as a couple of local bespoke shoemakers. Cleverly likely will cost me on the order of $6000 while the local bespoke options are closer to $2000.

Obviously at 1/3 the price, the local options won’t be equal to Cleverly. However, is there something significant you’d be suspicious that I would lose out upon (e.g. akin hand-padding in a jacket)–is there something I should be sure to look into before potentially committing to one of them?

As well, for a first bespoke commission, is it wise to go straight to one of the best (Cleverly), or is it better to start with less expensive options?

The appeal of the local shoemakers is largely to support a local industry as well as to save on the investment. However, a well-fitting shoe that will last me decades is the first criterion if I’m to be spending that kind of money.

Your insights, and those of other readers, would be most welcome!


Thanks Simon, that is very helpful.

One follow-up: what is the problem with a machine-made last, as long as it is original? Is it that machined lasts are made around a standard pattern of proportions constrained by the measurements taken, but they don’t take into account individual subtleties of fit (akin to made-to-measure v. bespoke in a sense?).

Overall, I don’t think I have a great eye for most finishings and don’t value them as much as other readers, with the exception of burnishing and patination–but I seem to remember you saying that this is the one point where Cleverly falls short.


This was the comment on machine-made lasts: “the first risk is that it is not true bespoke (perhaps an original last but machine made, for instance)”. Reading it again, I think I must have misunderstood–you probably meant a machine-made shoe on an original last.

The two local makers both apparently use original lasts. One seems to have them made by Springline, the other has them made offsite in plastic. So I assume part of the benefit of Cleverly then is an in-house last production. Otherwise, it seems they are hand-made, including hand-sown lasts.

Thanks for your advice and I will explore further.


Both adjust the last with piece of leather to improve the fit (assume the plastic one can’t be rasped), but I’m sure the Cleverly lasts are superior representations of a foot.

Many thanks for you advice. I feel much clearer now on what the trade-offs with the less expensive options are.

Reuven Lax

It appears that Saint Crispin’s does occasionally visit Toronto. I have a similar issue (narrower heel, wider toes), and have been quite happy with the fit I was able to achieve with Saint Crispin’ss modified last. Also the difference in cost between Saint Crispin’s and Cleverly far exceeds the cost of a ticket to NYC where Crispin’s has a showroom. I wouldn’t equate SC with full bespoke, but for me the fit and quality have been great.


Thanks Rueven. Saint Crispin’s would be of interest to me. They were visiting Toronto once or twice a year for a while, but it’s been over 22 months since their last visit and they don’t seem to have another one planned. So, sadly, it seems they may no longer coming to Canada now.

Reuven Lax

In your original Foster’s review you said that “it was the best fit (in a first shoe) I have had from any of the bespoke shoemakers I’ve used,” but you imply here that the fit isn’t great compared to other shoes. Did your opinion of the fit change with wear?


Hi, Simon. How much do you have to wear a pair of first bespoke to get a feel for the fit? Does it vary from maker to maker?

Adam jones

I have found my way back to this post remembering what you said about The Chelsea boots. I have one pair, black G&G which is strictly a dark denim boot for me but thinking of adding another one, in a dark brown or maybe polo suede.. in your opinion would a Chelsea or Chukka be a more sensible choice. As you know with me it is going to only be a denim/ very casual trouser shoe.



What are your thoughts on the below loafers with jeans? Too formal a shape?



Tan or brown in leather ok? I already have them in a mid brown.


Hi Simon

In terms of formality, where does cordovan leather sit? Given they’re smooth and shiny, are they as formal as calf?

Mustafa Hirji

Hi Simon,

Revisiting the post, I notice (1) you haven’t commissioned anything in oxblood/burgundy, and (2) you have commissioned only one derby amongst many oxfords.

I’m wondering why you didn’t do any shoes in oxblood–do you find that to be a colour that isn’t versatile enough (some seem to swear by this colour’s versatility)?

As for derby shoes, I assumed they would be pretty versatile, being appropriate from casual polos and casual shirts all the way up to blazers (and maybe even suits if it is a very formal colour of shoe).

I’m curious to learn more of your thoughts on the oxblood colour and the derby style.


Simon – when it comes to proper fit, my understanding is that the heel should be “hugged” whilst the toes have some freedom to move. If this is correct, how do you gauge non-bespoke fit when first trying a pair on, i.e. I’ve often been told that when first trying on a pair they should be quite snug, almost tight as they will loosen somewhat over time. I’ve had mixed results with such an approach.


So if I understand, if you were trying on a non-bespoke pair and they didn’t fit with a snug heel and freedom of movement in the toes, you’d move on to another size rather than hope the fit corrects over time?


Hi Simon,
I am interested to hear your opinion on RTW makers on purchasing a pair of shoes. I’m looking to buy a pair of black oxfords and / or loafers and I’m deciding between a few makers. I was wondering if you could have anything to say on the construction / quality of Cleverley RTW vs Crockett and Jones Benchgrade. I am debating between those, Carmina, and perhaps maybe grab a pair of Ferragamo Lavazione Originale when they go on sale. Interested to hear your thoughts on them or are they mostly similar just down to personal taste in style.


Hi Simon,

So given that Cleverly RTW is priced at 525£ you would say they are better than the 415£ priced benchgrade Crockett and Jones? Thanks for your comments on the brands, to be clear, I don’t intend to pay 500+ for a pair of ferragamos as they currently charge, but they do go on frequent sales for 250 or so which I think is a much better value proposition. I’d be interested to hear what other brands you’d recommend within the 400-500£ range if you feel there are better options.


Wonderful article! I could use some advice – I live in the Midwest U.S. where winters are snowy and salty, which I found will destroy shoes instantly. Any thoughts on smart boots that are up for the challenge?


Hi Simon,

Regarding suede Belgian loafers, what would be the three most versatile colors, in order of versatility? Would you day it would be dark brown, black, then midnight navy?

How do you pair black & navy suede loafers? Do the same principles apply for dress shoes?


Why two shades of brown? Dark brown for darker trousers/outfits and oak brown for lighter color trouser/outfits?


Looking at the Baudoin & Lange loafers and the “Oak” color seems dark, just a tad lighter than dark brown. When you say oak, would the “Tobacco” B&L loafer be the shade you are referring to?


I see – is it because you want the shoes to be darker than the trousers?


Following up my previous comment I’ve purchased two Cleverleys during their sale. They go nicely with the PS bridge coat might I add. Just wondering if you could comment a little bit on the whether you regard handwelted shoes such as Enzo Bonafe or Vass better than handgrade good year welted from Crockett and Jones or Cleverleys for about same price at retail?


Thank you Simon. I would also for the purposes letting other readers who might follow this thread know, Cleverley’s current RTW mainline also includes their previous semi-bespoke models that (I believe) predate the Anthony Cleverley line. These include the finer outsoles, elevated heel, and a very narrow waist with fiddleback as opposed to their regular RTW with a bevelled waist.


Simon, I have arthritis in my big toe which, as well as being painful, has created a large, bony lump on top of the joint. This makes wearing leather shoes for any length of time very uncomfortable. As such, I am forced to wear trainers around the office, only putting shoes on when going into meetings.
This is depressing as trainers with chinos (or worse, suits) look ridiculous. It is doubly depressing as it means wearing my G&G or Edward Green shoes for any length of time leaves me hobbling for 24hours.
Do you have any suggestions as to what I might try when wearing a suit or chino, shirt and sports jacket? I currently wear black trainers – the most plain I can find. The only other option appears to be the awful, cheap looking shoes that offer cushioning and comfort – as offered by Rockport, among others.
Thanks and keep up the excellent work.


That’s helpful, thanks. White trainers would be ok with chinos but a no go with a suit. I have come to the conclusion that when wearing a suit I’ll have to suffer wearing leather shoes while in meetings and switch to trainers otherwise.
One further thought – for the office, might some bespoke slippers substitute for shoes? From what I can tell, these look shoe like, but would obviously have a much softer and more forgiving construction for padding around the office.
It is very depressing indeed to see my carefully collected and looked after shoe collection gathering dust. The same with all of my suits, which I try not to wear now unless absolutely necessary.
Thanks for taking the time to reply.



Not sure if you get to read this, but it sounds like you have hallux rigidus. If it hasn’t progressed too far, you can have a cheilectomy. I’ve had the procedure and it made a massive difference. If it has progressed very far, you may have to fuse your toe.

Good luck with your toe.


I see that you have rubber soles on the chukkas. What is your general opinion on soles for formal shoes? Leather or thin rubber soles?


Hi Simon, thank you for this post! As I’ll be starting work next year, I aim to rotate a few versatile shoes. I will be working in healthcare and the attire is a dressier business casual (i.e. dress shirts with the sleeves rolled above the elbow and slacks) and suits are not worn at all. For this situation, I am deciding between a pair of dark brown punched captoe oxfords, Norwegian split-toe derbies, or penny loafers. Eventually, I’d like to purchase all 3 but I’d love to hear your thoughts on which to prioritise.

If it helps, I currently have a pair of black captoe oxfords and burgundy cordovan tassle loafers. Thank you for your help!


Thank you for your advice. What is the most casual attire that the oxfords can go with? I’m unsure if it will go well with oxford cloth button-downs and tailored chinos/cotton trousers if I do not wear a jacket.

As I may be getting it bespoke, I was thinking of getting it with a fiddleback waist and seamless heel. How would these details affect the versatility of the oxfords and what they can be worn with?

Lastly, would you recommend the loafer or the Derbies after the oxfords?


Richard Jones

Jimmy, it would actually be the opposite for me, in the environment you’ll be working in. For your work 3 x penny loafers will be the most useful: brown suede, cordovan, and a grain – no need for fiddle waist or bespoke. Going from suits to dress down last year, my dark brown oxfords aren’t getting any wear (unless I choose to wear a suit). In terms of formality, you’ll be smarter than your colleagues if wearing ‘good’ OCB shirts, cotton trousers and penny loafers.

If bespoke shoes is something you want to try (something I do not have experience in), go for the seamless heel, slim fiddle waist dark brown Oxford.

Choosing a selection of versatile styles, is less versatile than picking one that works.


Very nice shoe collection!!
I am from Spain, where it seems that dressing properly, particularly in an office environment, isn’t as important as it is in the UK… which leads to my inquiry: in all your posts you recommend wearing oxford shoes when you are intended to be dressing smartly with suit and tie, but is it actually necessary? I mean, provided the case you were wearing black tassel or penny loafers with suit and tie, which is in fact very common, conservative and accepted in Spain, would you actually feel ashamed or outstanding? Would it be such a big error?



Between snuff suede and polo suede, which do you think would be a more versatile shade. If it makes any difference, the style of the shoe is a Norwegian Split toe and I’m intending on wearing the shoes with jeans / chinos.

Thanks in advance.


I noticed that you prefer dark brown calf over museum calf? Are there any particular reasons? Also, is black adeleaine oxford as versatile as cap toe? Thank you,


Simon, thanks for this helpful post.

When ordering a first bespoke shoe with a maker at a trunk show, does it really matter whether one goes in in the morning or later in the day to be measured for the last, or is that only something for RTW?

And on a related point, assuming one ultimately wants to use the last for loafers, lace-ups, and boots, is there any advantage to ordering one vs. the other for the first pair?

I’m in particular interested in ordering a St. Crispin’s custom last, and just wondering whether being fitted in the AM for a loafer or the PM for an oxford will make any difference for future orders of boots, loafers, etc.


Apologies that I’m late to be posting a response to this. From personal experience, I can advise that Saint Crispin’s strongly recommends one get a lace-up shoe as a first commission, and leave a loafer as a later commission. I assume this is because getting the fit right on a loafer is much more difficult, and lessons learned with an earlier, more forgiving, fitting will help get the loafer right. I assume a bespoke shoemaker who may do multiple fittings can go straight to a loafer as a first commission.

John Goodmanstein

Hi Simon,

In terms of classifying the colours of some of your brown shoes, at least based on the photos in this article, I would have thought that the:

– G&G bespoke loafers are medium brown not light brown.
– G&&G bespoke Adelaides (after the patina treatment) are dark brown not medium brown.
– Cleverly bespoke quarter brogues are very dark brown (almost black).

Would you agree with the above?


Interesting article, as always. I have exactly the same issue with Chelsea boots. I have a nice dark brown pair from Santoni which look great on their own but I simply never wear them (at all).


Simon, comparing a suede, mid brown brogues (similar design as your black Cleveley above), with an adelaide oxford, as well in suede and same color! Which one would be a little more casual or more versatile to wear?

Fernando Ruiz

Hi Simon, what happened to that Norman Vilalta boot?


Along those lines Simon, have you ever requested a refund for pieces you have commissioned due to numerous fit issues? What is the breaking point? I’ve had 6-7 pairs of Lot 1 Levi’s jeans now and the fit is still off. Any advice?

I think an article on bespoke fit issues for readers would be very helpful. And what to do if a paid commission fails.


Thank you for making the great blog.
Now I am looking for the new shoes. Due to the problem of my flat feet, I always have an ache when walking and feel my C&J loafers aren’t in a good shape. So do you have any suggestion for the RTW shoes that solve this issue or should I go for the bespoke shoes?

Juan Huertas

Hi Simon. Reviving this old post, what is your current favorite oxford? I am trying to decide between a GG St. James vintage oak, or a EG Chelsea in dark oak. Your thoughts would be much appreciated.


Hi Simon! Once again a very informative post.
I just wanted to know whether can I wear a burgundy shoe with charcoal grey chinos/trousers?


Would oxblood shoes go with charcoal chinos/trousers?


I’ve been seeing some discussions in various forums that suggest oxfords should only be worn with a suit. Derbies for odd trousers. I am sure it depends on the material (suede vs calf), shine, and detailing or shape. However, it seems you’re comfortable wearing oxfords with a smart sport coat and trouser combination? I’m debating a suede derby versus an oxford at the moment.


Simon, any plans to update this post in 2021 as we follow the journey a decade on from 2010?


You mention cycling to work, which I find interesting. I’ll be starting my first professional job soon and I would really like to cycle to work. But I’m worried about it ruining my clothes. Shoes seem fairly easy to just swap out when you arrive. But what do you do to prevent the bike seat from wearing through the crotch of your trousers prematurely? Thanks.


Hi Simon,
I would like to be able to wear a pair of versatile black cap toe and a pair of black wholecut oxfords without any broguing so I can dress it up and down. Is this even possible, and if so, what details would be needed in order to create something like that?


Hi Simon,
I was wondering the difference between good year welt and hand welt. I was also wondering how easy it is to go between shoes that are good year welted and hand welted shoes without much of a difference.


wasn’t also a concern that often during resoling cobbler (yes even at the factory) might not care and punch a new holes with a machine, limiting how many times you can resole, but handwelting craftsman would use the same holes, so in theory you could resole unlimited times?


To be honest, I’m the only one that even thinks about resoling.

And I mixed up above hand sewn outsole with hand sewn welt.


Thank you Simon. Is there a comfort difference between the two types of welts?


Hi Simon,
I was wondering how versatile a split toe chukka boot would be, an example of which is https://www.carminashoemaker.com/norwegian-boots-brown-demasquable-80697, in a brown suede. Thank you in advance.


Thank you Simon. I used that link to give you an idea of the general look of what the upper looks like just in case you hadn’t seen it before. I also hope you enjoyed Pitti.


Hi Simon,

I hope you are well. Thank you for a very helpful post.

I commissioned a pair of bespoke from George Cleverly a few days ago. After some thinking, I went for the full-strap loafers (“Bradley”) in dark brown calf leather. As I am still a student, I thought I would get the most wear out of this hybrid style. Although I own a pair of penny loafers (Piccaddily) from EG, I have never had a full-strap ones. After reading your article, I became curious of how you would think of my choice of style, colour and leather as my first full bespoke. And do you have any tips regarding the details of the shoes including the stitching, colour depth/antiquing (if I want timeless/versatile hybrid shoes)?

I would be so grateful if you could please let me know.

Many thanks again as always.

Kind regards,


Hi Simon, I hope you are well. I think my last comment could’ve slipped through so I am reposting.

I recently commissioned a pair of bespoke full-strap (dark brown calfskin) penny loafers from George Cleverly (the “Bradley” model). As I don’t suit up often, I wanted to go for something that I can get the most wear out of when I dress up semi-formally/casually (i.e. polo/flannels, shirt/denim/chinos) – what do you think of my choice? And do you have any advice on what I should choose for the stitching, leather colour and other details?

Also, when I initially chose the style, I debated between this and dark brown oxford (as I read in your article that dark brown oxfords can go well with anything up to flannels and dark denims). Do you think I made a good decision on commissioning the pair I chose?


Yes, you’re right – sorry! For some reason, I did not receive any notification and couldn’t find my comment. Thank you.
In relation to my question on the dark brown oxfords being worn with anything up denim and chinos, what do you think? Since placing the order I have been debating whether I should change it to dark brown oxford.. thanks


Hi Simon, thanks for sharing. You make an interesting point: “[Oxford] is more formal than a derby and goes with anything up to chinos and jeans.” Could you please tell how oxford shoes can be paired with jeans and chinos?


Hi Simon,
I have kindly been gifted a pair of bespoke shoes / boots to be made by Trickers. I think from a crawl through the website you and comments have not covered Trickers in any detail and so perhaps you have a limited view however Ihad two questions would love your thoughts on

  1. Is there a style or material you would recommned from Trickers…I feel like they are known for boots however I assume in bespoke that should be equally capable across styles?
  2. I do not wear dress shoes regularly and would like to ensure that I get a pair that are simple, will be with me in 20 years and that I can wear regularly relatively casually. I typically wear loafers, derbys and some casual(ish) oxfords. Is there a style and / or leather type you would recommend (given the usual limitations of you not being me!); I know you have previoulsy erred against a loafer as a first commission…would you still say this?

As ever, look forward to any thoughts and watchouts you have


Sam – Trickers are particularly known for brogue shoes and boots. They are excellent at those and they will last forever. In my view they do other styles less well. That heavy, country style brogue is slightly out of fashion at the moment but in my view a subtle pair in dark brown should be a very happy and loved addition to anyone’s collection.


Hello Simon may i ask what is your view on chelsea boots as a high end bespoke? Would you say it’s worth it in terms of how itd look – eg looking more elegant than high end rtw or would you say it wont look much different as the design of all chelsea boots looks more or less the same? Im not sure if its a good idea to commission sth that is plain in design – or is it better to commission sth that demands more craftsmanship/patterns/etc?


That’s a good point – don’t think ive seen any rtw chelsea with a slim/fiddleback waist. I have flat feet which normally makes it difficult for the maker to achieve that waist – do you happen to know if this is a general issue with ppl with low arches or could some makers still manage to make a slim waist? Ever since one maker said that it’s impossible to achieve a slim waist for a flat foot, bespoke has somewhat become less appealing to me with that respect – would appreciate your input on this


Hello Mr Crompton, I am planning to switch all my RTW shoes to bespoke shoes. I want to start with casuals first- chukka boots, derbies and loafers this year and oxfords for next year. Do you suggest I order from one or a few different makers?

Ali Abas

Can you please recommend any 3d foot scan and bespoke Last maker?

Is 3D foot scanning for bespoke Last more accurate than traditional last making ?


Hey Simon, what would you say about chocolate brown suede oxford for a bespoke? Thought it could be a versatile week-days/weekend pair that could be dressed with suits and dressed down with chinos or even dark jeans.


That’s helpful to know Simon, thanks. Had always thought that anything suede would make it more versatile, but guess I shouldn’t push it too far. Been trying to decide what leather/colour I should choose for my oxford – I want something that could be worn in weekdays and weekend (not sure if oxfords can be used for both..?). I rarely dress in full suits.

Nice, where are you getting yours from? Do you know what leather/colour & how are you going to wear them?


Noticed that you haven’t commissioned any burgundy color shoes. Do you think dark burgundy oxfords can be worn with many different colors? Id be grateful for your view on wearing dark burgundy v dark brown shoes

Jack Linney

Your style has evolved substantially over the last several years, seemingly moving from wearing suits almost exclusively to a more casual look blending aspects of tailoring and heritage style. Looking back at this post with the benefit of hindsight, are there any style tweaks you would have made?

I have a few pairs of bespoke shoes. I never bought oxfords because they don’t work that well with my feet. I also have something of a “love affair” with single monks and loafers, so all but one are riffs on those two. The last few I’ve had made focused on interesting leathers that (in theory) cover the gamut of smart casual.