When: 2011

Lil Wayne proved in 2011 that no denim rule could hold him back. Weezy rocked women's jeggings (yes, women's jeggings) from Tripp NY. The polarizing fashion statement launched its own Twitter account and more than its share of jokes.

Danny Brown also learned that keeping it real in rap doesn't always pay off. The weirdo rapper tried to sign with 50's G-Unit Records back in 2010, but Fiddy rejected him because of his pants. "50 didn't sign me because I wore skinnies," Danny shared

However, not even O.G.s like Jay-Z stood a chance against the slimmer silhouette starting to trend in fashion. Despite claiming that he couldn't wear skinny jeans because "[his] knots don't fit" on "Swagga Like Us," later, Hov was rocking slim jeans right along with every other rapper.