Photo: Jonathon Kambouris

3 of 25
Old School: You can't wear head-to-toe denim.

New Rule: You can wear denim without slipping into Texas tuxedo territory if you pair pieces with different washes—a chambray top and dark skinny jeans, for instance. Or you can hedge your bets with this Rag & Bone jacket: a dip-dyed denim number that's dark on top, bleached on the bottom.
Rag & Bone, $275; Barneys New York, 888-222-7639.