27. The Cropped Black Trouser — Forever a staple (at least in our books), a cropped black trouser perfectly shows off sleek pumps or ankle boots, lengthens your legs, and is comfy, to boot. The only problem is figuring out a way to not wear 'em out!

Warehouse Slim Leg Trouser, $62, available at Warehouse; 3.1 Phillip Lim Jodphur Trouser, $350, available at Barneys.