16. The Oxford Shorts — Sure, it's not shorts' season yet, but oh man is it coming. And, nothing beats the heat while still looking sharp than a pair of oxford shorts. We prefer the traditional blue color way, with its ability to mix 'n' match with almost everything in your closet.

Gant Rugger Glen Plaid Shorts, $125, available at Barneys; RVCA Oxo Short II, $54, available at Need Supply Co.