$250, by Allen Edmonds
Cut from premium suede with a sturdy oiled leather sole and crafted in America with a Goodyear welt, it's clear from the start—these are not your average desert boots. No, these are Allen Edmonds' Amok chukka boots. What started out as a side project of the brand's head of production has gone on to become one of their more popular styles. And for good reason. Timeless and understated, they're more refined than your average crepe-soled chukkas. And thanks to the generously cushioned footbed and unlined suede uppers (which mold to the contours of your foot), they're more comfortable too. They come in three shades, but we're partial to the snuff brown, which complements everything from jeans and chinos to tweed trousers to navy and grey suits.