When it comes to classic footwear that every man should have in his closet, a pair of chukka boots definitely tops the list. Because it's something of a secret weapon shoe—it has the ability to add a nice contrast to whatever it is you're wearing. Pair them with your beat-up jeans or worn-in cotton chinos and let them give your dress pants a shot of relaxed cool. It's at once classic and current.

But who makes the best ones? And how much should you spend? That's a matter of personal taste and budget. We pulled on several different styles to put together this three-tier recommendation. Whether you need a reliable starter pair or are prepared to lay down twice as much for a pair that can be repaired and resoled over and over again, these are the suede chukkas that won't let you down.