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


  1. 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…

  2. Simon Crompton

    Oh dear, very frustrating.
    Worth trying an insole in the right shoe probably, though sounds weird that it doesn’t lace up fully yet there’s so much room at the back

  3. abitofcolor

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

  4. 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?

  5. Simon Crompton

    No it won’t, though you can glue something similar as a temporary measure, to see what the effect is

  6. 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!

  7. 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?

  8. 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.

  9. NicoStromback

    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?

  10. Simon Crompton

    It will do to the extent it makes the inside of the boot smaller, yes

  11. 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.

  12. 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.

  13. 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.

  14. 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)!

  15. 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)?

  16. Simon Crompton

    The fit of boots depends on the foot or leg to the same degree – I find it very difficult to find boots that fit, for example, as I have narrow ankles.
    I take the point about formality of boots in previous decades, but today a boot is always going to be less formal than the equivalent shoe.
    Finally, whether outsourcing is a problem largely depends on the company outsourcing. If they send out their own lasts, and take time to train the makers there, there isn’t much difference in quality. The problem is most outsourcers don’t invest this time.

  17. bespokeshoe

    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.

  18. 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″?

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

  20. Simon Crompton

    You can get deodorising or anti-bacterial sprays. Also, a lot of airing and cedar shoe trees are good

  21. 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).

  22. 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.

  23. Simon Crompton

    It’s inevitable…

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