2. Nike Air Max Penny "Orlando"

Year released: 1995 

Penny's first signature shoe set the tone for all of what was to come. The sneaker featured the visible heel Max Air unit with the "1 Cent" logo right above it, a pinstriped tongue (a nod to the Magic uniforms) and a PU support panel. Its great design and black/white/varsity royal colorway made these just as appealing for hoopin' in or rockin' to class, and Lil' Penny on the TV only heightened the appeal.