7. Spicoli gives himself a rap on the head.
Sneaker: Vans Slip-On
All Jeff Spicoli needed was some tasty waves, a cool buzz...and his checkered Vans Slip-Ons. He may not have done too well in the classroom, but Sean Penn's Cali stoner sure did a lot for laceless Vans. 1982's Fast Times At Ridgemont High still stands as a prime piece of '80s Americana, as do those checkered sneaks. Aloha, Mr. Hand.