Self-promotion will always be a must in hip-hop, especially if you’re pushing your own product outside of music. So, Hov rapping about his signature sneaker through Reebok on “What More Can I Say” off of what was supposed to be his final project, The Black Album, in 2003, was par for the course. In fact, the beginning of the 21st century saw fashion brands cozy up to rappers (think 50 Cent’s G-Unit sneakers). And if companies didn’t come a calling, the likes of Jay-Z (Rocawear), Russell and Kimora Lee Simmons (Phat Farm, Baby Phat), Sean Combs (Sean John), Pharrell and Nigo (Ice Cream, Billionaire Boys Club, BAPE), Nelly (Vokal, Apple Bottoms), and others created their own, flooding a market already dominated by beloved hood staples like Mecca, Ecko, FUBU, and Enyce.

And even though Shawn Carter put the throwback jersey trend in a coma, there’s no denying that for a portion of the 2000s, we were committed to Mitchell & Ness and their overpriced, oversized jerseys—complimented with durags (tied or untied), a Yankees fitted, grillz, and an iced-out chain and watch by TechnoMarine, or, if you were really balling, Jacob The Jeweler. And Velour jumpsuits were a chef’s kiss.

We were rooted in everything oversized, actually. White (or pink) tees and jeans two or three sizes too big were commonplace on the corner or in the VIP section of the club. Eventually, the masses did shift to Jay’s way of thinking in the mid to late aughts, adding both fitted designer button-ups and jeans to the closet, providing some grown man ish to their style.

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