Sperry Topsider for J. Crew Washed CVO Sneakers
Buy It Now at J. Crew, $75

Plimsolls are the fancy Euro term for any old canvas and rubber sneaker. Whether you stick with classics like Vans Authentics, Chuck Taylors, or Superga 2750s, you can't go wrong. Dirty 'em up all summer long, and throw them in the washing machine to freshen them up when they get rank. Just don't put them in the dryer. In fact, dry them in the sun for a cool faded look over time.