Air Jordan $1,885

Air Jordan 1 Retro High OG 'Chicago' 2015


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We've seen this silhouette — along with other classics like the 3's, 4's, and 11's — become much more than just sneakers. Sure, they look dope breaking some hopeless defender's ankles when you're playing ball, but they look equally fresh rocking them with a pair of jeans or a tuxedo. 

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The Jordan 1 is a staple of the culture. MJ did everything with effortless style.


The "Chicago" colorway is what most people think of when they think of the Jordan 1. Draped in the Bulls red, white, and black, this 2015 release saw the return to its most accurate construction since the first retro in 1994 — complete with Nike Air branding on the tongue. Simply put, these joints are the definition of dope.