When TLC hit the red carpet with Dr. Dre at the 1994 American Music Awards, they rolled through in some of the most oversized overalls seen in award show history. Now, as skinny jeans become even less taboo (we can thank the 2000s for that) thanks to dudes like Kanye West, Wiz Khalifa, A$AP Rocky, and yes, even Lil Wayne. For today's rapper, oversized is more akin to a longline shirt than it is to a copping your whole wardrobe in size XXXL. That's not to say that oversized silhouettes are on the out, but are we seeing rappers dressing like they came straight out of a Das EFX promotional photo? Not as much.