The Effect: They're appropriate for the sidewalk and the boardwalk.
Buy It Now: Stussy, $66

Yeah, portly guys and Hawaiian shirts have been going well together for years, and that hasn't changed. You just have to make sure to get one in a modern fit that doesn't look like it was a hand me down from dad or made by Tommy Bahama. Stussy's current collection offers a variety of fits and fabrics that wouldn't look out of place off the beach either. This one features a dope map print and won't look out of place on city streets either. It's like getting two-for-one.