Sperry pretty

I’m pretty sure that my brother (and his very fashionable girlfriend) wears Sperry shoes. I’m pretty sure that I’ve made fun of him for wearing them (along with his many other ultra-preppy garments, like J.Crew seersucker pants) – although I do it with love. So, I feel like a bit of a hypocrite when I say that I’m actually starting to dig the Sperry!

There’s something about this shoe. It makes me feel very summer, very nautical, very… Martha’s Vineyard. I feel like one wearing this shoe could trick someone into believing he/she is from New England (and no one could call the bluff). Paired with some chinos and a blue and white striped shirt (perhaps a bucket hat, as well), the whole outfit emits summer sophistication.

And there’s also the comfort thing. How comfy do they look? Now, as a non-owner of the Sperry, I have yet to strut around in these babies. However, they seem to be popping up everywhere and as far as I’m concerned they sure do look comfy! Check out some of my favorite Sperry looks now:

Sperry with mesh

Navy Sperry

Classic Sperry styles