Nike Air Tailwind "Kenya" 

Year (of Sneaker): 1992

Season(s): 1

Episode(s): 2, 6, 8, 19, 14 

Shawn impressed from the jump with the Kenya-tailored Air Tailwind classics that released in 1992. The OG-colorway built with thick mesh is one of the hottest runners of all time and was welcomed back in 2009 by sneakerheads who beat up their pairs in the '90s. Even though Shawn was living that trailer park life that didn't stop him from rocking the best.