Shoemakers can do a lot to help you decide which size is right for you. They can feel in which places your foot is hard against the edge. They can judge the clearance at the instep by how far the laces tighten. And they can look for any slippage of your heel. In the case of Lodger, they can even scan your foot to compare the fit with different lasts electronically.

But in the end, the true arbiter of fit is you. Only you know where it squeezes, where it is loose and where it hurts.

So you need to understand how leather changes. As it is a skin, it will stretch under pressure and reform. To a certain extent it will shape to your foot. This is reduced the more seams there are – leather stretches, seams don’t. So a full brogue will adapt much less than a whole-cut.

As a general rule, then, it is worth getting the size of shoe that is a little bit small, rather than a little bit big.

I had this choice when trying on a pair of shoes recently. The size 8.5 was very comfortable, but it laced all the way up with no gap at all between the facings. So over time, I knew that the shoe would become a little loose. And the right (smaller) foot already had a very small amount of slippage at the heel. I’ve solved this problem in the past with tongue pads (see post here). But that is obviously less than ideal.

The size 8 had greater room to lace up, but was tight across the ball of the foot. Not painful, but a little uncomfortable. So what to do?

Well, fortunately I have two pairs of shoes to compare to: two Edward Greens (rebranded as Ralph Lauren), one a full brogue and one a monk strap, one in an 8.5 and one in an 9. The 8.5 took a fair amount of wearing in; it was uncomfortable for months. But it now fits perfectly and will last for decades. The 9, on the other hand, was incredibly comfortable from the start but is now a little large – it required an extra hole in the strap.

The choice, really, is yours. Sometimes a shoe will fit perfectly, but often one will be a little bit big and one a little bit small. Then you have to choose: fit now or fit later.

It is also a question of personal preference to an extent – don’t forget that. Some people prefer their shoes a little loose all the time. Think back over previous experience and try and work out which you prefer. And bear in mind that leather will stretch.

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I think the size (up1/2 or down 1/2) has to do with the last. Some lasts lend themselves to 1/2 size down because they are more rounded. same applies to 1/2 up with a more elongated narrow shoes. Let’s not forget that 1/2 shoe size is equal to (typically)1/6″ and sometimes even 1/8″ again depending on the last.


this is a great point that you make, and this is something i only realised recently, buying shoes that are just tight will have a shoe that fits perfectly for most of the shoes life.

great blog, keep up the good work.


I have been searching the Internet for a resource on leather stretching, and no one seemed to know what they were talking about. But you are clearly talking from experience as I’ve had the exact same problem. It’s strange that no one at a shoe store has ever mentioned that a full brogue will stretch less. Anyhow, you have me a huge headache (by understanding that a two half-sizes can fit, but pick fit now or fit later) and I want to thank you for that. Keep it up!


can you please elaborate about your article “fit now or fit later”. You mentioned that you had two pair of EG shoes one was hurting for months and fit now perfectly while the other one was instantly comfortable and is now a little bit loose.

I would like to know what you mean with hurting for months i.e. where exactly was the shoe too tight and is now comfortable?


I have just purchased a pair of Johnston & Murphy’s that are sized as “wide”, but seem quite narrow. I’ve been wearing J&M for years. I don’t know if the leather itself is too stiff, but looking at my “socked” foot next to them, the laws of physics would seem to be violated by getting into those shoes. Odd, never had this problem before with J&M, and the ones in the store (wrong color, I ordered after trying on), fit perfectly. Stymied. I wonder how long it would take to break these monsters in!


Thank goodness for this article! It has cemented an ideal notion first thought of as wishful thinking at best. At worst, a hopeful yours truly succumbing the stark realism that my beloved, if a tad ostentatious statement making kicks may require a total refund. I could come across like an imposter and time waster. I’ve not long been aware of the traditional shoemaking styles and what qualities this can signify against just a recognised popular brand that makes shoes – because why not? They make everything else! So niavely I thought that the only difference between a $100 and a $500 pair of shoes was mostly the designers brand name attached to it and if lucky some better materials. I saw the Oliver Sweenies and Paul Smith as the big hitters? Clearly they both make some beautiful footwear options to the uninitiated – but its a huge market out there for the discerning gent, or lady to invest into and for the timeless shoe classics. So, and given some newly acquired learnings I purchased a pair of whole cuts from Melvin and Hamilton to whom I stumbled across at 3AM browsing the web trying to make certain I wasn’t missing a better deal elsewhere. Silly move really as some double Monk Straps were being held for me at an outfitters in town, ultimately I had to cancel that order but I had to have them! However, upon arrival they are somewhat uncomfortable, a bit small in the width of the shoe. The company asks customers to in fact order at least half a size less as their shoes come larger than our true fit expectations. As a UK Size 10 I had to order a UK 9 and the package arrived this afternoon. I actually reside at a place where many opinions could be acheived quickly, a Hostel so believe me I got the naked truth. All gave a massive thumbs up for this quirky ‘dragon’ embellished whole cut so now im hooked. It makes sense they would mould to my feet though I still may have to go to the traders in town and ask the question of what realistically can be done without sacrificing the shoes longevity or It’s ‘eventual fit’. I just thought I could share my experience with you all and continue to learn – I still desperately want a decent pair of Monk Straps and could probably do around 2-250 Pounds Sterling so any thoughts on my next purchase would be met with gratitude. Thank you and thanks again for the insightful and concise piece. Lewis

Brett Royle

I have recently bought a pair of loakes in wingtip brouges , they fit nice and snugly no pain and I went a full size down but now they are worn in I have room in the heel area and with the laces tight together as it can be in feel I should have gone 1.5 sizes down, my wife mentioned heel grips or a thicker pair of socks but thickening socks look ugly I may have to double up on my dress socks and get a professional opinion next time I buy.


I recently bought a captoe boot, it fits perfect. But when I used it about 2-3 hours,it start hurting my edge little toe. It hurts around the horizontal stitch area on the captoe. The question is, can that stitch area stretch overtime?


is there any bad effect after stretching it ? this is pull up leather


Hello Simon
I buy shoes half a size smaller than is snug when new so they will be snug after wearing in (which usually takes a month). I am wondering what will happen when they are refurbished on the original last: Will the excess stretched leather be cut away? Will I be able to wear them in again or will the leather not stretch again? Would it be better to buy the right size and have them refurbished back down to size after they are worn in and loose?
Thank you for this excellent resource.


I recently bought leather work shoes that are good for nursing.. it’s perfect on my left foot but on my right foot it feels tight around my big toe.. should I go half a size up?


Hello Simon,

Thanks for the informative article(s) and all the great work you do with PS.

I noticed the Lodger link doesn’t work as it still points to the old Blogspot website. Luckily, the URLs differ only in the domain name ( vs, whereas the directory (/2009/04/my-left-foot-afternoon-at-lodger.html) is the same for both. Albeit I don’t know how your website is implemented, I’ve seen my fair share of code and I think it should be fairly easy to replace all the old Blogspot occurrences with the updated URLs (or to have any Blogspot instance redirect directly to its equivalent rather than the homepage).

Thanks again for the great work.