Nothing screams prep like a pair of Sperry boat shoes. It’s been a while since they were a part of my daily rotation — flash back to my Catholic high school days with khaki’s and popped polo shirt collars.
That idea of the boat shoe is what sticks with most people, but they can honestly be worn with any style of dress. It’s a very practical and simple shoe that just works. I’m normally on land, but I’m close enough to the Marina to put these to good use.