Chris Brown's new album Fortune drops tomorrow. Perfect timing, as he won Best Male R&B Artist and Entertainer of the Year at last night's BET Awards. While it hasn't been a smooth path all the way through for Breezy (ahem—Rihanna, daytime TV interviews, the alleged altercation between him and Drake), you can't deny that he's made some of the biggest hits in the last few years.

If you've kept up with his career, you'd know that those hits haven't always followed one sound. The same can be said about his style. He's experimented with many looks, which have led to some pretty questionable 'fits. But we will give the 23-year-old crooner props for improving his style as of late. So in honor of the album drop, we're taking a look back at his most memorable looks throughout the years—the ups and the downs. Here's Chris Brown's Style History.