Shorts: Levi's denim cut-offs, $30

Shoes: Vans classics, $42

Shorts: Dockers washed plaid, $44

Shoes: Clarks desert boots, $95

A Short Supply

The key to overcoming a fear of shorts is finding a flattering fit and pairing them with the right footwear. Ask any woman, and she'll tell you the key to making legs appear longer is to show more of them. Shorts should hit at, or just above the knee, so lose the baggy pair of shin-skimming cargo shorts. That same woman would also likely tell you she prefers men's legs muscular over emaciated. So would the poor guy with the chicken legs.

Shorts: J.Crew seersucker, $55

Shoes: Peal & Co. for Brooks Brothers, $264

Shorts: Hickey herringbone twill, $87

Shoes: Cole Haan wing tips, $201