Gant by Michael Bastian, $295
"I like cargos because they're another option to jeans, cords, chinos or dress pants—they kind of combine the best of all of these," says Michael Bastian who's offered a pair in nearly every collection he's presented for both his main line and Gant. "I've worn them with everything from a tank top to a dinner jacket, I mean, you can't ask for much more range than that." The trick, according to Bastian, is that it's all in the proportions. Look for slim, relaxed fits with a lower rise and authentic military details and hardware. The pockets shouldn't be too big and they should hit just above the knee.. "Its a delicate balance, and there's a lot of crap cargos out there," says Bastian. "So many in fact that a lot of guys are hesitant to try them, but they really should give this new generation a try."