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I can wear both the 9 and the 9.5 in Allen Edmonds 5 last. The 9.5s require that I wear heavier socks and they lace up pretty much tight. The 9s are a bit snug in the left foot and feel better with thinner socks.

Which way should I go: a bit large or a bit small? With creasing and wear, I'm not sure whether shoes like this actually get a tad larger or smaller over time.
 

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I can wear both the 9 and the 9.5 in Allen Edmonds 5 last. The 9.5s require that I wear heavier socks and they lace up pretty much tight. The 9s are a bit snug in the left foot and feel better with thinner socks.

Which way should I go: a bit large or a bit small? With creasing and wear, I'm not sure whether shoes like this actually get a tad larger or smaller over time.
So I think this is a great question which most people struggle with to some degree as shoes, other than bespoke, are most likely never going to be a "perfect" fit for your foot. A wise person once said to me two things to remember, the shoe will never be smaller than the day you buy it and better to err on the side of slightly larger than smaller. His point was, during the course of the day your feet are giong to swell a little and a little dscomfort on the tight side could become a great deal of discomfort. I believe navagating between these two themes will help you find a succesful fit. If it is a little tight in the width it will likely strech out. Shoes which are too short will most likely just remain uncomfortable and, perhaps, unwearable.
 

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Personally, I would say go for a different last, one that fits better and you can only wear the shoe in one size, not two. To answer your question, go for 9.5.

Shoes are more comfortable to wear, whether your feet are swollen or not, when they are slightly big compared with them being slightly small.
 
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Too large or find a different last. Feet will "grow" slightly over the course of the day, which would exacerbate a "too small" shoe, but it may make the slightly larger size manageable.
^ +1

A shoe that starts out as too snug when you put it one is going to feel even tighter as the day wears on and your foot expands. If you can't find a different last that you like, go with the larger size. It give you more to work with.

I have some shoes that are just a tad larger than an ideal fit. I've gone to a Walgreens and bouugth some insole inserts and put them in the shoes to take uo that smidge of extra space. They coast about $3. This has worked well. And I can always remove and replace them if I need to.
 

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2 problems

1) Feet expand by the end of the day if you're walking around alot - so you might want to go a bit bigger
2) Quality shoes tend to stretch after a few wears - so you might want to go smaller.

I had the same issues with C&J's and ended up buying 2 pairs which turned out to be a half-size too big after 3 wears even though I was worried they were too tight at first.
 

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As someone else mentioned, get some sort of inserts from the drug store - they may work out well.

If it's AE, ask at one of their stores if it's possible for you to order a pair of shoes in two different sizes. I seem to remember reading somewhere that they'd do that. (I don't know if they charge more for that, however).
 
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