I have a history with Sperry shoes. When I was a kid, my dad always wore leather “boat shoes.” Then when I started dating my boyfriend, I discovered that he was a fan of them too. Naturally, not one to be outdone by the boys, I wanted a pair of my own!

Two years ago, I bought a really cute pair of fabric Sperry Top-Siders that are a preppy madras print. They are getting a little worn down now, so I’m thinking of grabbing a leather pair to replace them. I love the Angelfish style that comes with a fun little stripe of fabric down the side of the leather. For a funky look, I’d choose the leopard pony hair style. For a more subdued look, I’d go with the tweed fabric.

I love these shoes paired with a cute pair of rolled up boyfriend jeans, a white button down shirt and a colorful scarf. How would you wear them?