Chris Brown's Funniest Fashion Fails

Image via Complex Original

WHAT: Larry King Live

WHEN: 2009

Complex Says: Oh man. The infamous bow tie. Apologizing on national television for pummeling a young songbird right in her gorgeous head repeated times while driving and possibly cheating on her is a challenge. Pulling off sincerity dressed like a damned ventriloquist's dummy is impossible. Also, kinda funny. That sweater!

WHAT: Paris Fashion Week

WHEN: 2010

Complex Says:

There's actually nothing wrong with the clothing. The accent color of the coat offsets the white denim and tee splendidly. And then you see the shoes. Oh. The. Shoes. Ladies' gladiator sandals on top of slouch boots? WHY??!!!

WHAT: Us Weekly Hot Hollywood Stars Who Care Event

WHEN: 2010

Complex Says: How many squirrels must die for you to look fly. And by fly we mean, MAHAHAHHAHAHAHAHAHAHHAHA. Gross.

WHAT: "Champion" Videoshoot

WHEN: 2010

Complex Says: We called him a wee equestrian Christmas ornament in the past. For exactly the reason you see before you.

WHAT: New Year's Eve at Club LOVE, DC

WHEN: 2010

Complex Says: The first fail is participating in a dougie contest with John Wall. You will lose. Second, is wearing no shirt at the club. Third is wearing a jacket over an invisible shirt. Tattoo is not clothing, dun.

WHAT: 105.1 Powerhouse Concert

WHEN: 2009

Complex Says: Just because you're the only human being alive that dances almost as well as Michael Jackson, doesn't mean that you have to wear a replica of his jacket, too. Sequins are a choking hazard. Especially when you have an entire bag of dicks to eat for being such an egregious sartorial offense. The terminator gloves and sneakers look like garbage bags wrapped in electrical tape and the sunglasses the absolute worst. Also, let's just go ahead and get it out of the way right now. Does he look a little, husky in this shot or what?

WHAT: Graffiti Album Cover

WHEN: 2009

Complex Says: Um, is that a sash around his waist? A cummerbund? High-waisted pants? Corset? Control-top pantyhose? Either way, all of them go into the FAIL category. More things that are wrong: robot arm. Poseur electric guitar on an R&B album cover. OD high-top boots. Super-weird Mucinex cartoon monsters on the bottom.

WHAT: 106 and Park

WHEN: 2010

Complex Says: Shawl-collared cardigans and raw denim are both great trends, so thank God Chris has the power to make unfunny cool things hysterical. That face is priceless for example. The pink buffalo plaid sweater is real tight in the middle, and the jorts are "HULK SMAAAAASH" small.

WHAT: Fashion Rocks

WHEN: 2008

Complex Says: Chris totally stole this from a chick who works Medieval Times. And then punched her in the face. Kidding! (Not really). The awkward stance and creepy square-toed shoes don't help his situation either. Fashion Rocks, but this dude dresses like he smokes 'em. ZING!

WHAT: Jean-Paul Gaultier Fashion Show, Paris Fashion Week

WHEN: 2010

Complex Says: Oh man, Breezy's turtleneck is see-through but can we talk about these pants? The amount of harnesses around his legs is an S&M nightmare. Muthafuckin' G-I-M-P.