Best Bet: Matt Bernson Booties

New Yorkers are hard on our shoes — we walk everywhere, and cheap heels can be worn down in a weekend. These wedge booties are comfortable and easy to walk in without sacrificing height. The canvas-covered wedge and center seam give them a sleek, streamlined look, making them an easy complement to jeans or skirts, and the heels last longer than typical soles before needing a trip to the cobbler.

Matt Bernson canvas booties, $178 at Anthropologie or online.