The Rapper: A$AP Rocky
What He Wore: An "oversized shirt" (that looked a lot like a dress)
WTF Was He Thinking? Long before Young Thug started rocking women's dresses and openly admitting it, Rocky rocked the dress, er, "shirt" that you see here. He denied that it was a dress later, but it sure looked like one to us. You be the judge.
Photo Credit: HipHopWired