1 / 10

#TeamBreezy - The sexy singer took his school-boy style to another level when he wore this edgy denim and leather combo jacket with a brown and blue cap and a fur backpack.(Photo: Gregg DeGuire/PictureGroup)

Photo By Photo: Gregg DeGuire/PictureGroup

2 / 10

Perfectly Prepped - We love how Chris mixed things up with this gingham sweater and cropped denim shorts.(Photo: Rob Loud/PictureGroup)

Photo By Photo: Rob Loud/PictureGroup

3 / 10

Dapper Dude - Dipping into dapper mode, Chris Brown transformed his R&B style into a James Bond–inspired look with this tailored tux and bow tie.(Photo: Gerald Holubowicz/PictureGroup)

4 / 10

Swag on 1000 - When Chris Brown stopped by 106 & Park in 2009, he gave us a little West Coast flavor in a checkered shirt, suede boots and black leather gloves.(Photo: Brad Barket/PictureGroup)

5 / 10

Tie One On - Let the jokers crack jokes, but the bow tie has come back in a big way. Chris put his own twist on a classic accessory by pairing it with a leather jacket and gray and black vest.(Photo: Michael Burr/Picture Group)

6 / 10

Love and Louis - Chris understands that accessories can make an outfit. The fly blockers, “Louis” scarf and animal-print sneaks transform his all black gear. (Photo: Michael Buckner/Getty Images)

7 / 10

Cool Dude - This look perfectly captures Chris's effortless laid-back style. The denim vest and checkered blue and white shirt are complemented by the singer's best accessory—those sexy lips.(Photo: Martin Roe/Retna Ltd)

8 / 10

Poppin' Colors  - Breezy lit up the stage at the Essence Music Festival in a black T-shirt, black jacket and bright Carolina-blue pants.(Photo: Erika Goldring / Retna Ltd.)

9 / 10

Boyish Charm - Chris showed off his boyish good looks in this yellow "Charlie Brown" style cardigan, T-shirt and cap. (Photo: Shareif Ziyadat/PictureGroup)

10 / 10

Eye Candy - Few people can pull off a red and white suit without looking like a candy cane, but somehow Chris did it. It's not our favorite look, but we have to give him props for taking a risk.(Photo: Frazer Harrison/Getty Images)