LL Cool J's Most Iconic Video Looks

Jan. 14, 1968, a star was born. LL Cool J entered the world with no idea he’d go on to redefine hip-hop, not just with bars, but with undeniable style. By 16, he had already released his first single, “I Need a Beat” in 1985, kicking off a career that would change music, fashion, and culture forever.

With the release of his debut album Radio, featuring the breakout hit “Rock The Bells” that year, the Long Island native helped turn Def Jam into a powerhouse label. His confidence, commanding presence, and fearless fashion choices made LL Cool J the blueprint for cool across the ’80s, ’90s, and 2000s.

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Rocking bold gold chains, oversized Kangol hats, iced-out two-finger rings, and Adidas and Fila tracksuits, LL Cool J’s look was as influential as his lyrics. In a 2020 interview with WWD, the rapper—born James Todd Smith III—made it clear that his fashion wasn’t just about trends, but about culture.

“When I recorded Rock the Bells in 1986, my heroes were people who embraced and lived the four elements of hip-hop,” he explained, which are djing, breaking, graffiti, and mcing. “It’s true and real, and we really lived it.”

From album covers to award shows, LL’s larger-than-life style followed him throughout his career, especially after his fourth album, Mama Said Knock You Out, dropped in 1990, earning him his first GRAMMY in 1991 for Best Rap Performance. The album depicted the rapper wearing a large double-plated gold chain and a ginormous gold ring.

As the years have flown by,  LL Cool J’s impeccable sense of style has never skipped a beat. He continues to weave elements from his glory years into his looks today, whether he’s walking an awards-show carpet, commanding the stage, or acting on set.

A recent case in point came in December 2025, when the rapper was spotted performing at Philadelphia’s First New Year’s Eve Concert and Fireworks Show, to kick off the nationwide holiday. LL took the stage in a bold cheetah-print jacket, paired with a leather newsboy cap and effortlessly cool sunglasses, proving once again that his fashion instincts remain timeless.

As we celebrate LL Cool J’s 58th birthday, let’s take a look back at some of his most iconic video looks and style moments.

1. The Gold Chains Era – “I’m Bad.”

LL Cool J turned heavy gold chains into a hip-hop power symbol, pairing raw street energy with an undeniable star presence. His early Def Jam visuals helped define what rap luxury looked like before it went mainstream. This iconic look is on full display in the music video for “I’m Bad,” in 1987, where LL rocks layered gold chains alongside his legendary Kangol Bermuda bucket hat, an outfit that became synonymous with his dominance and confidence.

2. Adidas & Fila Tracksuits – “I Need Love.”

Long before athleisure ruled fashion, LL Cool J was already setting the standard. His love for matching tracksuits—like the gleaming Adidas tracksuit he sported in “I Need Love” (1987)—often paired with fresh sneakers and that bossy gold jewelry, cemented the look as both functional and fly. The combination of sportswear and swagger helped shape hip-hop’s everyday uniform.

3. Two-Finger Rings & Ice – “Mama Said Knock You Out.”

LL’s oversized rings and bold jewelry choices helped establish the flashy-yet-masculine aesthetic that later generations of rappers would emulate. His accessories weren’t just add-ons; they were statements of status, success, and self-made power. One of the most recognizable images in hip-hop history, the Mama Said Knock You Out album cover features LL wearing a massive double-plated gold chain and ring spelling his name, perfectly matching the album’s aggressive confidence. The visual became just as impactful as the music itself.

4. Award-Winning Swagger At The 1991 VMAS

After winning Best Rap Performance at the 1991 GRAMMY Awards for Mama Said Knock You Out, LL Cool J’s fashion reflected his superstar status. His looks blended bold jewelry with tailored silhouettes, leather, and his signature sky-high bucket hat, signaling a transformation and a new era of hip-hop excellence. A video shared by the LL Cool J Archive YouTube page captured the rapper shopping for a fly green suit alongside model Cindy Crawford in 1991, to wear at that year’s VMAs. Crawford took one look at the rapper and said, “Oh my god, that is so cool,” a spot-on definition of the hip-hop icon’s incredible allure.

6. Modern Performances, Classic Energy – “Proclivities.”

Whether performing on stage or showing up at cultural moments, LL Cool J continues to channel the confidence and fashion instincts that made him iconic in the first place, effortlessly blending nostalgia with modern polish. In 2024, the rapper did exactly that in his music video for “Proclivities” featuring Saweetie.

Dressed in a black baseball cap, a black long-sleeve work shirt layered over a tank top, and iced-out jewelry draped across his neck and wrists, LL delivered a masterclass in refined swagger. The look subtly nods to the flashy Radio era while feeling perfectly tailored to who he is today—grown, confident, and still undeniably sexy.

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The post 58 & Fine: LL Cool J’s Most Iconic Video Looks appeared first on MadameNoire.