This depends slightly on the type of boot you buy, and the materials used. It’s also a big deal since these boots don’t have laces. Let me run through some scenarios.
General Guidance
Every time you put a boot on, you should be using the pull tabs. You need to hear than thunk when your foot pulls into the boot. If your foot slides in with no resistance, the boot is too big. If it physical hurts you to pull it on, the boot is too small.
Cheaper Boots With Synthetic Components
Once you add anything modern—plastic heel counters, plastic shanks, and memory foam footbeds—you want the boot to fit perfectly from wear number one. If it’s too tight, it won’t get better. For every brand on this list, don’t be afraid to send boots back and ask for a new size.
Traditionally Made Boots with Totally Leather Components
Here, you want the first few wears to be tight. Not so tight you can’t move, but it’s OK if they’re a little uncomfortable. If you sweat in the boots, walk around all day, or (honestly) drink too much, they might be a little hard to take off; that’s fine, ask a partner to help.
You want this because leather has a good bit of give built in. When a boot is made fully from leather, it starts tight, but after a handful of wears molds over your foot. It’s a beautiful process, and there’s no easy way to fake it.
Reptile and Fish Exotics
Mammal leather (ostrich, as well) is great at conforming to the foot. Reptile leathers less so, but they still make good off-the-rack boots. Fish, namely shark and stingray, do not stretch at all. I really would only recommend going bespoke for those.
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