santoni fatto a mano su misura2

I have received a few questions on this 2009 post about how shoes wear over time recently, and note that there is no post that sets out the basics of how a shoe should fit.

Let’s start with a simple summary. A shoe should be tight at the back and loose at the front. It should hold the rear of the foot firmly, to stop it from slipping, and provide enough room at the front for the toes to move freely.

Movement of the foot is what causes rubbing and blisters on the heel or ankle, and can cause discomfort to the toes by allowing the foot to slide forward. When deciding which size of shoe to buy, therefore, make sure the ankle is held tightly around the opening of the shoe. Bespoke makers sometimes describe the fit as being ‘drum tight’, and it is the reason that a bespoke shape to the heel cup is so useful.

You will often find good makers lacing the shoe tighter than you are used to, for similar reasons. As with the fit of trousers on the waist, tightness in the back of a shoe takes only a few minutes to get used to. You then forget about it (again, as with a trouser waist) as the shoe never moves to remind you of its presence.

That old post made the point that leather stretches over time, and that this is a good reason to buy a shoe that fits snugly around the heel and ankle. It’s good advice, and I wish I’d followed it with some early purchases.

It is for this reason, too, that it is good to have some room between the facings (the two sides that are laced together across the top of the foot) so the shoe can be tightened further as the shoe stretches – or rather, moulds to the shape of your foot.

If it’s impossible to find a shoe last and size that fits in this way, you can try an insole or a tongue pad. Insoles are readily available but have the disadvantage of pushing the foot slightly up, out of the shoe. A tongue pad is inserted into the tongue itself, pushing the foot down instead.

It’s not easy to find a shoemaker that will put in a tongue pad, as the tongue has to be unstitched and then sewn back up again. But I have had them done at Cleverley, and Corthay offers a particularly good service in this respect – helped by having an expanded factory and such a big made-to-order business.

Before resorting to such alterations, though, it is always worth trying several shoemakers in the price range you are looking at, as each will have subtly different lasts and different options for MTO. Good, welted shoes will last you upwards of 10 years; it is worth spending the time to get the fit right.

Image: my bespoke Santonis

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Good timing Simon, as this is smth I was wondering about recently having some major issues with two AS pairs on the same last (109). Got the first one (model Hunt) almost a year ago, out of the box the fit was perfect, snug around the heel (to the point of having problems getting my feet in them) with just enough room on the front, no foot sliding, perfection. There was a small gap between the facings which was also good news as I remembered my other pairs stretched enough to get that ‘closed’ so I wasn’t worried. I thought this is the perfect last for me and was happy I finally found a shoe that fits well. Shame that the shoe got looser and looser over time, which isnt great considering my right foot is slightly smaller than my left. Currently the right shoe is too big imho, with it being laced up as hard as possible (as much as my foot can take) the facings still don’t come closed (almost no stretch here?) but the heel is definitely not held solid (and I can just about get my index finger in between the heel and the foot with the shoe laced). The inside section between the lacing and the heel has a tendency to bow as I walk which adds to the annoyance as everytime it happens I can see a massive gap between the shoe and the foot (‘too big’ effect). The left shoe being on the larger foot seems of course better and tighter although I dont think I could down-size a whole pair as my left foot would simply kill me.

Whats more annoying is that another pair (different model) on the same last seems to be 0.5 size larger for some reason, now that will definitely end up too large for both feet when its broken in. Assuming it breaks in the same amount of course…



Great summary. It is all about a solid fit in the heal and enough room in the toes to “play the piano”.

Mike Small

Very interesting piece Simon. I was intrigued to read about the tongue pad. This is an option my father (who was a podiatrist) used to recommend to aid in fitting. I think he used to recommend a adhesive felt pad stuck to the rear of the tongue. This probably achieved the same effect as the tongue pad at considerably less expense . However, I suspect it didn’t last as long, and not many men will want to be sticking felt to the insides of their calf leather Goodyear welted prized positions?


Great post, Simon. In this age of internet shopping and cheap High St brands, many people have no-one to advise them on fit and therefore lack knowledge/ interest.

Traditional shoemakers in Jermyn St and elsewhere offer good advice on fit. However, if J.M. Weston or G&G can offer several widths on every formal shoe, why don’t the others do more?

The main reason for people wearing badly fitting shoes is the lack of fit options! If someone has wide feet, they end up wearing shoes two sizes too big!

Sir Fopling Flutter

This is a really good point. It’s shocking how few options there are in different width fittings. Why isn’t this available in the UK, while US manufacturers (ie, Alden and Allen Edmonds) offer a huge range of widths?


I’ve never seen an ‘average’ pair of feet. They don’t exist. If the good shoemakers offer half-sizes, then they should offer 2-3 widths per size. Less choice, more widths please. You can get away with it in a soft synthetic Nike trainer. Not so with a solid Goodyear-welted pair of tanks! That said, you can’t expect a bench-made shoe to fit like bespoke.


I have had similar issue with a purchase I made about a year ago. A great look pair of boots that cost around 800 USD. They had a good fit in the beginning but recently have given away around the wider part of the foot. My feet have thus started to slide around in there. You adding some form of insole will help with that?


It’s quite easy to reduce the size or width of your shoes when they get re-soled (if it’s available in their range already). Just ask them to do it for you.


Simon, this is a very useful article, thank you. I’ve had a loose heel problem on only one pair of shoes. I elected to try a heel pad which worked very well. However, periodicallty the pad has to be replaced which is annoying,but it a small inconvenience compared to getting rid of a shoe that I really like.


As someone with both wide feet and a a very high instep I really struggle to buy shoes that fit well. The problem is never that the shoe will not be tight enough or the heel slips but always the room in the toe box. The lack of stock of different width fittings is a real problem. I find I often get different advice from different staff of the same Jermyn street brands. It is often just a shot in the dark ordering a MTO wide fitting and hoping the fit is right. A £700+ gamble on fit is incredibly frustrating. I really wish more brands would offer different width fittings in a range of lasts to try on.


Thanks Simon, excellent article. I had a lovely pair of Cheaney brogues bought for me at Christmas on their 125 last, and as I’ve found the fit excellent and extremely comfortable I just last week purchased a pair of black oxfords on the same last. I wore them today for the first time, and while my left foot is fine (and the shoe on that foot was perfectly comfortable), I’m sitting here with an open blister the size of a 10p piece on my right heel from where it was slipping – incredibly frustrating to say the least (and very painful until I could take the shoe off)!


Good article Simon. As with many I find shoe fitting can pose problems particularly at the more modest end of the market where construction and materials are getting progressively cheaper (and made in Countries with no tradition of the style/manufacturing technique). Though RTW shoes can be difficult I find boots are much easier. Whilst they are less formal the Victorians used them across all aspects of dress (styles such as the Chelsea boot was originally designed for Queen Victoria). I therefore wonder whether boots are, overall, more ergonomic (as they can fasten higher up on the foot/ankle). Bespoke aside Simon, what has been your experience (boots more comfortable than shoes?) and could you give us your thoughts on the aspects of footwear formality; can the correct boot be seen as appropriate formalwear? One last question; do you think that the massive outsourcing of RTW shoe manufacturing to the Far East is producing a universality of output and thus a worsening of fit (accepting that some excellent UK manufacturers remain)?


To keep a good fit don’t forget how important it is:
– to use a shoehorn to put on your shoes – using your finger stretches the back over time
– not to use one shoe to push down the back of the other to take them off! (This will damage the upper at the heel and break down the stiffener which gives the heel that lovely fit in the first place).

Also be mindful that different styles of shoe and leathers will have less or more stretch…so don’t let that gap on the facings be too wide if you prefer a closed facing.

Fit on the edge

Dear Simon,

You wrote one must not worry about question content because you’ll order it. My question is: How should collars fit, more specific: If 16 1/2″ is on the border of tolerance, what are the dangers of changing to 17″?


What to do with bespoke shoes that smell (of sweat)?


To the problem of shoes that are found to be say half a size too big after having worn them outdoors, the solutions already described will perhaps be more elegant, but one quick option is to wear thicker socks. My suggestion is Thorlo’s dress socks going by the code DLTX. The added benefit is that comfort is enhanced and blisters are minimised, whilst the shoe still feels as one with the foot. (Colours are unfortunately limited to either black or dark brown).


If shoes for properly as you describe, will there be very little signs of wear in the heel lining due to very little rubbing? I’m wondering if your best fitting shoes show any signs of rubbing on the heel lining (or anywhere inside the shoe), and this is just inevitable. Or should you try to find a shoe that fits such that there are no signs of rubbing inside the shoe.


I ordered a couple pair of shoes online that I really like (@$350.00US per pair) size 12US M or “medium” width. I have a slightly wider foot but not huge and a relatively high instep. I have never needed to order wide or any other special specification in the mostly inexpensive off the rack shoes I have worn in the past. These shoes fit very snug and feel perfect in the heel and mid foot but are a bit tight in the forefoot – not really at the widest ball of foot but just forward of that at the base of the toes- not hurting just tight. The length feels right and I can wiggle my toes freely but not a lot of room. When laced snuggly (not as tight as I can) there is about a narrow “V” shaped spacing between the facings from 1/8″ at the toe to about 3/4″ at the top (due to my high instep?). The manufacturer offers a wide but they are not available at the moment and dont know when they will be. I have to return these by 1/15/16 for refund bit am unable to try “wide” by then. I am hoping the leather will give a little with wearing and become perfect. What are your thoughts?


Edward Green were kind enough to send me two pairs of suede Asquiths to try on, since I have no dealer nearby—a 7.5 and an 8. I, too, have the annoying right-foot-is-slightly-smaller-than-the-left problem, so sizing based on all the advice I’ve read here is tricky, and bespoke may happen down the road. In English shoes, I’ve had the best luck with 7.5UK sizes on account of the tighter heel and 1-2cm of gap that I get at the top of the closure. That said, when I put on the 8s, there is a sort of feeling of “relief” my feet give at first, because the toes feel less constrained. I can—for sure—move my toes around in the smaller size shoe, but my big toes (toenails really) point ever so slightly upwards at their tips, so what is probably adequate room in the toe box feels slightly constraining in the big toes as they’ve sort of reached their limit. But I know that the heels suffer in the size 8 and getting the facings to tighten sufficiently around the smaller right foot can become a problem. I also have a pair of 7.5UK Crockett & Jones half-brogues that fit the same way and evoke similar feelings. Do you reckon I’m fine to stick with the smaller shoe? I recall reading something here that the “right” fit tends to be tighter than you’d think.

I must say, the last on these Asquiths is very sleek and interesting in the toe; sort of half-chiseled, half-rounded, and it changes depending on from what angle it’s viewed. A very handsome nip in at the waist. Lovely.


Hi Simon,
The toes are definitely happier in the larger size. Here is the gap in the closure when tied tightly with fairly thin Paul Smith socks: comment image?dl=0) What do you make of it? Too close, particularly on the right? I suppose the tongue pad will counter that somewhat. If you give it the nod, I will pull the lever…


Of course. You’ll be held harmless for any shoe-related misadventures.


Simon, would you give the same advice for (goodyear-welted) loafers? I’m considering a pair of C&J Sydney loafers, on the same last as a half-brogue I own. Knowing what I know now, I would have bought a half-size up in the half-brogues to give my toes a little more room and dealt with any size issue with a tongue pad. I wondered if I should treat these loafers the same way, despite no laces, being familiar with the last.


Hello-wondering what brand of shoes are in the picture – I like the color and style of shoes- thank you


I’ve recently purchased a pair of Edward Greens on ebay and I’m unsure of whether they fit well. They’re snug, almost tight at the front and loose at the back; the opposite of what you described in the article. I’m afraid if I will size up in width or length the heel will be even looser. I’m starting to think bespoke is my only option at this point for my odd feet.

David McLoghlin

Hi Simon, this is a helpful article, thanks. Having recently invested in a pair of Alden dress shoes (black calfskin, Dress Oxfords, RTW, plain toe), I have a fit question. The fit in the heel is good, and the toe box also. However, there’s something of a tightness across the vamp, if that’s what it’s called, or top of the shoe. As this is my first pair of dress shoes of decent quality, and I don’t have much experience of good leather-soled dress shoes, I’m wondering if they will naturally stretch a little bit with time, being calfskin? I’ve read that Cordovan won’t. Although I’ve only worn them at home a little bit to gauge fit, I’m seeing the beginnings of creases between the toe box and laces, and worry that the shop mightn’t exchange them for a wider fit model, if that exists. Thanks so much, David.


Thanks Simon, that’s spot on, I appreciate it. All the best with Permanent Style in the New Year. Thanks for your piece on The Armoury Chinos:

I live in New York, and will definitely pay them a visit. David


Simon,I really understand how your appreciation of classic style fits in with the modern man.However,your commissions,whether it be suits,shirts or shoes can be a little bit
expensive..should I buy RTW or just go bespoke? Ihave been thinking a lot about shoes recently(I’m sure you’ll understand!) and I would really like to see you analyse the difference in fit between a top grade Churchs’,Crockett and Jones,Edward Green,Gaziano and Girling and John Lobb(Hermes).Perhaps,the more expensive footwear will have slightly better leather (Green,Lobb,G&G) but I am more interested in fit…compared to bespoke.Can any of the above RTW compare to bespoke?Certainly,in my experience bespoke or MTM by an experienced tailor easily surpasses RTW in clothing.The only reason why I have never purchased bespoke shoes is that their cost compared to the benefit is so small…..or at least to my bourgeois sensibility’s.


Thanks Simon.A problem I have with RTW shoes is the comfort v aesthetics conundrum. Let’s say that I try on a size 10 shoe….it does’nt fit as per usual because it’s not wide enough…. so I turn up the notch one or two points and ask the assistant for a wider 10.The fit around the toes seems good in the larger shoe but the heel area is now too large to fit my ankle.Also, the wider shoe lacks the sleek elegance of the original one.
So I now try a size 10.5 or even 11 until I find the right balance between looks and comfort.
Sometimes,a longer shoe just looks better.If I look at say at an Oxford in a 10 on my right foot and just compare it to an 11(in my experience 10.5 or 11 are very similar) on the other foot …the latter wins hands down…to mix metaphors.


Hi Simon and everyone,

I bought some Alexander McQueen combat boots a week ago at Bicester, the price was so good I had to buy them.

Anyway, they are rock solid, any advice on breaking them in, softening them up?

I’ve heard soaking them in water helps.




“A shoe should be tight at the back…should hold the rear of the foot firmly, to stop it from slipping.”

Fitting RTW shoes has always given me trouble. I often go with a size 43 (holds for most shoe manufacturers), however, because of this post’s advice I’ve decided to go a size down than what I usually get. Take for example Vass: I have a pair in 43 that fits me fine but there is some space in the heel; however, I purchased a pair of 42 Vass oxfords that truly grip my heel. While most new shoes will invoke mild pain, including blisters, the 42 shoes add additional heel pain but only after I walk in them for some time. (Moreover, the 42s have space in the front, but the vamp feels slightly tight….)

I have scoured forums and videos across the digital ether, and the advice coming from US sources in particular could be construed as contradicting Simon’s advice. For example, US podiatrists and shoe sales associates advise that one should be able to slide an index finger–snugly–in between heel and the back of the shoe…it shouldn’t be an easy maneuver for the index finger to slide between heel and shoe, but it still should be possible. Going back to my RTW Vass challenge: for size 42, I have to struggle to get my index finger–up to the middle phalanx part– between my heel and the shoe; for 43, it will fit “snugly.”

So how does one check for “tight at the back”? Should you be able to insert your index finger between heel and the back of the shoe? If that’s not the proper way to test for heel tightness, what is?


Hi Simon – first off, congrats on being full-time on PS! It’d be quite neat if you started off a community where PS “members” or readers could engage in meaningful conversations about style (maybe on a Slack group of some sort?)

I’m not yet in a position where I can commission a bespoke pair of shoes, and I’m struggling to find a pair of ready to wear shoes. My feet have narrow heels, are a borderline C/D width, and have a relatively low instep. I’ve checked Carmina + Crockett and Jones lasts and I’m flying to NYC to try some out. Do you have any recommendations about brands I should check out? Any advice on this front would be enormously helpful.

Finally, if I were getting a bespoke pair, I live in Toronto where it gets quite rainy often, so I’d want something that was resilient in the weather. I would get rubber (or half rubber) for the soles and, as for leather, any recommendations? I have heard pebble grain or suede are more resilient in wet climates.

Richard T

I sympathise with AG. I have a similar problem with a narrow heel and low instep. I haven’t tried Carmina, but have found some Crockett & Jones lasts to be a reasonable compromise. Surprisingly, I’ve found that none of the higher end RTW makers have lasts that work at all for me. The best fitting shoes I have are Church’s Chatsworth brogues, which are an astonishingly good fit. I’m not sure how much better bespoke would be. The Chatsworths were a higher end product for the company and certainly used a better grade of leather. Unfortunately, Church’s don’t make the Chatsworth any more, although I’ve found that some retailers still have the odd pair in stock (sadly not in my size) retailing at £695.


Hi Richard – thanks for the comment here. I actually ended up doing an MTO order with the Carmina Inca last, and it’s been fitting me quite well. What I’ll do, if necessary, is get my cobbler to stitch a piece of matching leather around the heel cup, and it works phenomenally well based on the experiments I’ve done on older pairs.

@Simon, I still have to respond to yours, sorry for the delay!

Richard T

Thanks, AG. That sounds like an interesting solution. I recently tried tried some of the RTW shoes by G&G. The young lady who served me in Saville Row was incredibly helpful, but we couldn’t get a good fit – nothing to do with the shoes, just my odd feet. She suggested that if I went for an MTO pair, they could insert heel pieces, much as you’ve suggested. Apparently it’s something they often do for loafers.
An update on the Church’s – the discontinued 137 last is a really good fit for me, with a perfect grip at the heel, and they may be willing to resurrect it as a special order for me. I’m also going to look at their Crown Collection range next week, which is a much higher grade than their standard ones and are at a similar price point to EG and G&G. The young lady I dealt with at the Jermyn Street store couldn’t have been more helpful. Whatever I end up going for, It was great to see such high levels of customer service from both G&G and Church’s.


Hi Simon

I recently purchased a pair of Islay Crockett and Jones boots. They are lovely, I went back and forth on which size to purchase. I went for a half size smaller when deciding on two different sizes as there was so much extra leather over the top of the boots on the larger size and the shoes were not snug on my feet without resorting to an insole which I didn’t want to do.

However I am getting terrible blisters on my inside ankles. Which are very painful. Is this just part of the process? I have only been wearing them for a few days. Should I just stick with it as the leather around the ankle will give? I can wiggle my toes although my little toe on each side rubs a bit as the leather is still very new.

It would be great to get your advice, thanks


Hi Simon,

I have narrow heels and wide toes – my small toes basically stick out sideways. The only shoes I’ve been able to get a reasonable fit on are boots with supple or stretchy leather, like unlined suede or chromexel. Even sneakers generally do not have enough toe room, while dress shoes slip at the heel even when the facings are overlapped.

Any suggestions for finding shoes that fit?


Thomas Stephen

Hi Simon,

Ideally, for bespoke shoes should the arch support on the insole perfectly follow and fill the arch of your feet along the whole length of the arch? Should you be able to feel the arch support firmly press against the entire length of your arch while you walk?


Thomas Stephen

Do you find that the firmness of the arch support increases after breaking in the shoes? i.e. I assume that as the foot bed moulds to the shape of your feet, your feet would sink slightly deeper into the insole which I would imagine makes the arch support feel more pronounced than during the fitting stage?


Taking bespoke out of the equation, what is the most comfortable dress shoe; style & brand? An unlined loafer? Something else?

I ask because I have troubled feet but don’t want to be relegated to casual footwear.


Thank you Simon. By Dovers I assume you’re referring to the Edward Green Dover? May I further ask what (if anything) is shared between the Dover and the Alden loafer that make them more comfortable? Are they perhaps a bit wider, do they hug the foot in a certain way, is it sole construction?


Hi Simon
References to George Cleverley in several threads made me check out their website, I did not have that maker in the radar. For some reason I fell this time for the covered elastic sided styles, e.g. the Jack. I knew the style long since but had never appreciated it until this time. I haven’t seen you cover it and it seems to be really unusual in RTW ranges. Would you be so kind to comment on a few points?
1. Where does it classify in the usual categories of shoemakers in regard of “lacing” system e.g. Oxford, Derby, Monk… It’s neither.
2. I think I have read in the past that the system allows a particularly good fit to the foot. Is that true?
3. As mentioned I do not find it in most RTW ranges, do you know other makers in the C&J level to offer it?
Thank you!

David N

Hi Simon,
My feet have a narrow heel and waist and a fairly wide toe. Based on comments and replies I’ve found on PS, finding a loafer will be a challenge for me. One issue I keep encountering is that while the length of a shoe is perfect, the heel doesn’t slip, and the toe-box doesn’t feel cramped, there seems to be a hard raised area just beneath the ball of the big toe. Is this just a sign that my toes are too close to the inner edge of the toe, and that I need a wider toed shoe? Or is something else at play here? Also, is there any chance of this area going down as the footbed conforms to my feet? Many thanks for all the invaluable information over the years!

David N

Thanks, Simon. I’ve experienced it with Sid Mashburn’s Italian penny, Cobbler Union’s Henry, and a loafer from Spier & Mackay. Guessing I just need to try a maker who offers more width options, or maybe just something with a more…sigh… “sensible” toe.


My shoes make a lot of noise while i walk in them. Does this happen with your shoe and how could I make it stop?


When the sole of my shoe hit the surface then it makes a squeaky noise.


Thank you for the post Simon. I need some advice please. I got a pair of size 8 on square chisel toes Oxford from Stefano Bemer after trying on the their fitting shoes. While the length of the shoes fit, I am getting heel slips and there is some gap on top of my instep. I think the instep and heel cup are big for my feet. Do you have any advice on how this can be improved?


Thanks, Simon. I will give that a go.


Great post, Simon.

A question about boots: I recently acquired a new pair of cavalry boots (Heschung) that are quite roomy at the front – I can move my toes freely – with a half a thumb-size free space. The heel sits fine, neither too tight nor too loose with thin summer socks on.

Do you think the boots are too big and may become even bigger over time, or are they just fine?

Your advise would be highly appreciated.

Edwin Rothengatter

Hi Simon,

I have small ankles and heels compared to a wider forefoot. Recently I’v acquired the islay boot from crockett & jones. The size is perfect and my feet don’t slide around but my ankle feels barely supported. The instep also has a tiny bit of space (I attached a pictured with an comparison with my red wings)

Basically I’m looking for a tongue pad that’s permanent (I don’t like the look of the white tongue pads). I’v found a cobbler who is willing to thicken out the tongue enough to fill up the excess volume. My question is, what kind of material is used in your permanent tongue pads. I guess the outer layer is suede/leather. But what about the filling. Should I try a natural rubber or would memory foam be good as well.

Thanks in advance!

Edwin Rothengatter

Cheers, thanks for the information. I’ll council with my cobbler.

Have a nice evening!