24. Boat Shoes

Formerly associated with preppy douchebags with names like Chip, Tripp, or Prescott, these yacht-ready kicks were soon seen on the feet of producers like Pharrell Williams. As they gained more street-cred, collaborations from folks like Ronnie Fieg for Sebago and Band of Outsiders for Sperry Topsider made them desirable to both hypebeasts and the fashion-obsessed. Our personal highlight of this trend? When Complex Editor Damien Scott went toe-to-toe with J. Cole on the basketball court... while rocking boat shoes.