Who popularized it: Thirstin Howll III, Kanye
When we were influenced: 1988, 2004 

Thirstin Howl III's infatuation with Ralph Lauren came full tilt in 1988 when a love-scorned female called him a "low life," which he flipped into a worldwide group of 'Lo lovers. And while his underground rap career has taken a backseat to it, Howl's influence on the Lo-Lifes has been substantial in the hip-hop community.

Fast forward 15 years and a Chicago-based rapper enters a throwback-jersey, tall-tee arena donning popped collars on pink Polos and Bear sweaters. And guess what? It stuck like glue and he would go on to lead a fashion revolution from then on.