The prep boy kings, it wasn’t until Prada put these on the runway did anyone really start wearing them. First of all, if you’re over the age of 30, forget the boat shoe altogether. If you’ve just graduated high school these might catch your eye, and if you can’t get them out of your head, just don’t wear them with anything but linen. Do not wear socks, and stick with the classics like RM Williams, Sperrys, or Timberlands.