41. Lil Wayne

Sure, Wayne earned himself a spot on our list of most stylish celebrities of 2011, but we can't deny that he's made some pretty serious style offenses. Congrats Weezy, you are officially the best/worst-dressed celebrity. The word “jeggings” is a terrifying concept in general, exponentially so when in reference to a nearly 30-year-old male's signature style. Add a skintight sag on that shit, and you've got a horrible example being set for the youth of America (we're looking at you, Justin Bieber).