shirtingfantasy
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I will add to what has been said by stressing that in the case of Chelseas, perhaps more than any other shoe (with the exception of loafers), fit is essential. As many have mentioned, the elastic sides don't really provide support so the shape of the leather is doing all the work. thus, starting with a nice fitting last is THE most important aspect of selection.
depending on your foot of course, the biggest problem I've found with Chelseas (I've owned 10-12, right now just have 3) is the shape of the heel counter and waist. if the heel is too wide or not structured enough, it'll be a nightmare to wear because your foot will continuously slide. if the heel and waist are tight and adapt well to the shape of your foot then you can have extra space in the forefoot and the shoe will still feel set in place and stable.
that is why a brand like Carmina is a great alternative: you can first try on at least 4-5 of their lasts, and then build the Chelsea you want around that last (grain or smooth leather, wholecut or traditional 3 piece, storm or regular welt, single, double leather or rubber sole, etc.). they have chiseled lasts, almond toe lasts, round toe lasts, wide or narrow, etc. But any other company that offers the same level of customization or variety of lasts will work, and there are both higher and lower end companies that do this. of course, the alternative is to find a last/model from a company that works for you OTR, which does happen for a lot of people, but requires you go to multiple stores and also a bit of luck.
Some suggest sizing up for boots, I think it only works if you wear thicker socks when wearing boots in general.
Many poor fit issues are in fact wrong size / last. Just that people don’t see the heel gap when they buy a pair of boots.
Boots that fit well should be very difficult to take off.