5. Tailored Shorts
We stole these shorts from our 2013 Fashion Risks list. Fitted through the waist with a slightly loose thigh are a lot more forgiving than your standard summer short. This is a nice change from a typical menswear look and can beautifully showcase a pair of gorgeous gams.
Splurge on This: ADAM Slouchy Shorts $78
Photo Credit: Shopbop.com