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Trendsetter. Provocateur. Icon. Bad Boy. One can say many descriptors about Bobby Brown, but will any really encompass all that is the generation-shaping and ever-intriguing figure that does his influence justice? Probably not. But his enduring legacy is one that speaks volumes. As we approach the premiere of his highly anticipated A&E biography and mini-series, airing Memorial Day weekend, and the launch of his digital cover with our brother site Cassius, we’re counting down some of Bobby Brown’s most influential style moments.

The Gumby Haircut

Bobby brown gumby haircut

Source: Michael Ochs Archives / Getty

Fans were surprised to discover Bobby Brown’s trendsetting slanted do was actually an accident, which became a trending topic after the BET miniseries The Bobby Brown Story, starring Woody Mcclain. Bobby’s Gumby cut sparked an entire look circa the release of his music video Every Little Step.

Knee Boots And Mini Dresses

Not only did Bobby Brown inspire men’s fashion, but he also shaped women’s fashion in the late 80s with his Every Little Step music video that featured video models wearing blazers, knee boots, and mini dresses.

The Bad Boy Image

Bobby Brown rightfully earned the nickname the original “Bad boy of R&B” during the height of his career. He personified an unapologetic attitude that translated into his music (think: My Prerogative). “I was tired of the teeny-bop thing,” Brown told The Post in 2017. Long gone were the days of Candy Girl and the “hard-headed” Bobby Brown emerged. “Back then, I was definitely hardheaded,” he says. “After I went solo, I was rich. A millionaire at 18 years old. You couldn’t tell me nothing. I didn’t want anyone’s advice, and, obviously, I got into some bad situations.”

Dance Trends

Brown’s transcendent 80s album Don’t Be Cruel is a benchmark in music for many reasons. It catapulted the New Jack Swing sound and Bobby’s solo career after being kicked out of the popular group New Edition. His Alek Keshishian-directed music video Every Little Step also introduced fans to the ‘Roger Rabbit’ and ‘Running Man’ dance crazes.

Shoulder Pads

Bobby Brown At The Apollo

Source: Rita Barros / Getty

Bobby’s suspenders, biker shorts, and shoulder pads personify style in the 80s and early 90s.


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Bobby Brown’s Most Trendsetting Style Moments  was originally published on