If you need ankle support, you want THICK leather and a high shaft (8” or more). Bootmakers like Nicks, Whites, Drew’s, JK, and Franks all fit the bill. Their leathers are so thick that boot making machines can’t work the leather, and are therefore made by hand.

I own multiple pairs from the makers above due to crappy ankles and the need for serious arch support. No other boots come close, and I’ve work a lot of different boots before finding these guys. They suck to break in, but they’re super durable, incredibly supportive, and almost infinitely repairable.

Among them, Nicks is probably my overall favorite, but you can’t go wrong with any of them.