We get this question a lot! The trouble is, every brand has different shapes, styles, and to some extent sizes. Here's our expert opinion on how to best find a pair of cowboy boots that can fit you, even if you're buying online. Size Up, Size Up, Size Up! If you wear a size 9 in a standard lace up sneaker, no matter the gender, we do not often see folks walking away from our shop with a size 9 cowboy boot. They often end up buying (and loving) size 9.5 to 10. Sometimes a full size and a half... but keep reading. Even if you get your pair in the mail (or are trying them on at a shop) that feel a full size too big, consider the following: You have room for a cushiony insole. Insoles aren't just for support, there's some that are designed for pure cushy comfort. Walking around in most used or new cowboy boots can feel hard on the feet because you're essentially standing on two pieces of hard leather or leather and rubber. Our modern-day feet are much more used to comfort, so try to give it to them when possible. There's the benefit of that extra volume filled, so the boot actually looks like it fits better too. No more wrinkly boots as you walk. You are standing on a cushion, filling the extra volume of the boot, and you still have the extra bit of length, which means your toes aren't cramming to fit that pointy shape. (For square-toe boots, folks tend to walk away with something a bit closer to their street-shoe size) When it's hot out, your feet need room to swell a bit. When it's freezing out, you can wear a thick wool sock. What are some defining features of your foot shape? Do find most shoes are too narrow for you or too wide for you? There's typically a corresponding letter next to the boot size. This letter comes from the shape of the last the boot was formed on. Generally speaking, B tends to be a standard woman's width (slightly narrow), while D is the standard men's width. A will be quite narrow. More than one A (AA, AAA, AAAA), more and more narrow. C is a common women's width, which is slightly more wide than a B. E is wider than the average foot. EE, EEE, EEEE, more and more wide. With that understood, say you typically find most shoes to fit too narrow, then you'll want to avoid A, B widths when we are talking about women's feet and definitely men's feet. For women's sizing, C and D widths are really reasonable options for wider feet. All this gendered advice to say, more room is better than not. Size up. Have an insole to try out, like we do in the shop. Sometimes even a pretty thin insole makes a big difference.