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10 of Chris Brown's Best Style Moments Over the Years

Check out the top looks from the stylish singer who snagged four BET Award nominations this year.

Chris Brown has some serious street style! With a style evolution filled with designer gear and fresh kicks, the “Go Crazy” rapper has landed on many best dressed lists. 

RELATED | BET Awards 2021: Stylish Men On The BET Awards Red Carpet

As we countdown to the 2021 BET Awards on June 27 at 8/9C p.m., we found it highly appropriate to take a walk down memory lane and highlight the star’s most swagged out looks over the years—including his trendsetting ensemble at the BET Awards. Keep scrolling to see the fly 'fits worn by Chris, who snagged a whopping four nominations this year.

  1. 2005: Billboard Awards

    Just weeks after the release of his self-titled debut album, Chris Brown walked the Billboard Awards red carpet rocking a crisp white tee and baggy jeans. The singer added to this look with a charcoal gray jacket and matching Nike sneakers. Classic chic!

  2. 2006: The 48th Annual GRAMMY Awards

    (Photo: KMazur/WireImage for The Recording Academy)
    (Photo: KMazur/WireImage for The Recording Academy)

    Flashing his pearly whites, Breezy made his grand debut at the 2006 Grammys. The young entertainer looked sharp in a fresh white evening look, which he paired with a chocolate-brown suede blazer and matching shades. Effortless cool!

  3. 2006: The 37th Annual NAACP Image Awards

    (Photo: Milan Ryba/FilmMagic)
    (Photo: Milan Ryba/FilmMagic)

    Later that year, the handsome singer continued to wow us with his dapper fashion choices. While walking the red carpet at the 37th Annual NAACP Image Awards, he caught our attention in a black tailor-made suit fit for a star. His silver tie and polished black-and-white oxfords added to this smart look.

  4. 2008: Sony/BMG Grammy After Party

    (Photo by Charley Gallay/WireImage)
    (Photo by Charley Gallay/WireImage)

    When you’ve got swag, you show it off! Showcasing an unexpected combination of upscale fashions and edgy streetwear, the trendsetter walked down the red carpet in a white cardigan, striped button-down, and bright red jeans. To keep things chill, he completed the look with fresh Jordans, a red snapback, and a backpack to carry his valuables.

  5. 2011: "Justin Bieber: Never Say Never" Movie Premiere

    (Photo: Gabriel BOUYS / AFP via Getty Images)
    (Photo: Gabriel BOUYS / AFP via Getty Images)

    Look at how those diamonds glistened! Rocking a neck full of custom diamond-encrusted, cartoon-inspired pendants to match his eye-catching diamond earrings, CB showed up to support Justin Bieber’s Never Say Never movie premiere looking fly.

  6. 2015: BET Awards

    Breezy is the king of keeping things casual on the red carpet, even when his outfit is fiy-ah! Rocking a crisp white tee and black shorts, the singer really made his look pop at the 2015 BET Awards with a custom embroidered varsity jacket, featuring floral designs on each sleeve. Even his designer shades looked effortless.

  7. 2016: iHeartRadio Awards

    (Photo: Jon Kopaloff/FilmMagic)
    (Photo: Jon Kopaloff/FilmMagic)

    Not many people can pull off a matching sweatsuit on the red carpet, but CB isn't one that's crippled by fashion rules. While attending the iHeartRadio Music Awards, fans were impressed by his fresh white ensemble that featured pops of color on the sleeves and one knee of his fitted pants.

  8. 2018: Demi Lovato’s "Tell Me You Love Me" World Tour

    (Photo: Kevin Mazur/Getty Images for Philymack)
    (Photo: Kevin Mazur/Getty Images for Philymack)

    As an artist, Breezy has never been shy about changing up his style. Debuting his blond waves, the “Look At Me Now” singer had all eyes on him when he was spotted chillaxing in an oversized orange sweatshirt, a black denim jacket, and loose-fitted skinny jeans.

  9. 2019: Compound 15 Year Anniversary

    (Photo: Prince Williams/Wireimage)
    (Photo: Prince Williams/Wireimage)

    Street style, but make it memorable. Clearly getting the memo, the famous star made the asphalt his runway by wearing a boldly patterned button-down, bright yellow pants, fresh Nike sneakers, and an eye-catching diamond chain with a matching diamond watch. So icy!

  10. 2020: The 62nd Annual GRAMMY Awards

    (Photo: Jon Kopaloff/FilmMagic)
    (Photo: Jon Kopaloff/FilmMagic)

    Chris Brown served up a sweet father-daughter moment on the Grammy Awards red carpet. With his daughter Royalty Brown by his side, the “Yeah 3x” singer worked the cameras wearing a colorful ensemble that featured a two-toned sweater, black pants, and cream-colored dress shoes. We especially love his colorful and bold hair color choice for the night. So daring and do dead-on!

    Watch the 2021 BET Awards on June 27 at 8/9C.

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