Kevin Federline in the Nike Dunk Pro High SB "Unkle Dunkle"

Girl: Britney Spears
Year:
2004
Complex Says: "K-Fed did two things right in life: got his hands on plenty of exclusive Dunks and knocked-up one of the richest pop stars in the world. Despite since looking like a deadbeat and ballooning up to 250 pounds, you could say he's done alright for himself."