Tag Archives: sperry

Style Guide: Sperry TopSiders

Even if you don’t consider yourself to be a sailor you should consider gettin’ yourself a pair of hip Sperry Top-Sider boat shoes. These shoes will give you some much needed grandpa swagger, but only if you wear them right!

Rule #1: NO SOCKS! Simple as that. Anyone who’s actually sailed the seven seas will tell you the same thing.

Rule #2: While wearing Sperry’s with shorts it’s imperative you keep the shorts short!!! If they touch your knee or go past your knee, then reconsider your shorts. You also might want to reconsider your entire wardrobe if you wear shorts past the knee.

I bet that lemonade tastes reeeaaal good.

^he swears it’s a sachel, but we all know it’s a just a purse…

Rule #3: If you’re wearing Sperry’s with long pants, then cuff ‘em. Your ankles should be showing! If you were actually sailing the seven seas you wouldn’t want your pants to get all wet. Ask Popeye he’ll tell ya how it is!