See 16 of the Best Style Moments in Hip-Hop History

Hip-hop may be known for its genre-defining beats and legends from Tupac Shakur to JAY-Z, but the industry is also just as known for the iconic moments they’ve contributed to fashion history.

As hip-hop rings in its 50th anniversary, we rounded up 16 of the most memorable style moments worn by titans in the industry. As a genre inextricably intertwined with fashion, these artists have stood out for not only their music, but also their style.

Starting with the Salt-N-Pepa and ending with Doja Cat, here are 16 iconic fashionable moments in hip-hop history.

Salt-N-Pepa in Their “Push It” Jackets in 1988

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In what have now become iconic outfits, Salt-N-Pepa — a.k.a rappers Sandra “Pepa” Denton, Cheryl “Salt” James and DJ Spinderella — donned jackets emblazoned with phrases like “Idol Maker” and “Let There Be Music” and images like the comedy and tragedy masks and the Salt-N-Pepa logo for their “Push It” music video. The look has become synonymous with the girl group and continues to be recreated today, even as a Halloween costume.

Queen Latifah in 1990

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Queen Latifah embraced her heritage from the beginning of her career, proudly donning a colorful kufi and a matching outfit with statement gold earrings. As one of the first trailblazing female rappers, she set the stage for many to come, even after she pivoted into a career in Hollywood.

Tupac Shakur at Club USA in 1994

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In March 1994, six months before he was shot, Tupac enjoyed a night out at Club USA, one of New York City’s glitziest nightclubs at the time. The event was a party for the cowboy noir thriller Red Rock West so Tupac showed up in his best wild west attire. He wore his signature bandana — a look he came to be known for — and paired a brown leather vest with a plaid button-down and baggy jeans. For accessories, he went with a gold chain with a cross.

Missy Elliott at the Lilith Fair at Jones Beach in 1994

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Missy Elliott performed at the 1994 Lilith Fair — a music festival meant for women empowerment — in a black leather blow-up suit that came close to mimicking a garbage bag. Why? “I don’t know, cuz I’m Missy,” she responded to a fan wondering the same thing in 2019. Elliott rejected the hyper-sexualized costumes that were the norm for female stars and made the audience focus on her skills.

The Notorious B.I.G. Outside His Mother’s House in Brooklyn in 1995

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As one of the most legendary hip-hop artists, Biggie Smalls made waves in the fashion industry with his signature paperboy hats. In this moment from January 1995 — just two years before his death at 24 years old — Biggie is donning a leather jacket and a jersey while he rolls a cigar outside his mother’s home in Brooklyn, New York.

Lauryn Hill in 1998

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Often recognized as one of the most influential people in hip-hop, Lauryn Hill released The Miseducation of Lauryn Hill in 1998 and came out with accompanying promotion images, including this one. While a simple outfit with a purple vest sweater paired with a mesh skirt, strappy sandals and big hoops, Hill embraced late ’90s fashion — can’t forget the choker! — and showed the industry who she really is.

TLC at the 1999 MTV Video Music Awards

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The girl group of the moment, the iconic TLC, showed up to the 1999 VMAs in matching outfits as they took home the Moonman for best group music video for their hit, “No Scrubs.” The threesome, comprised of Tionne “T-Boz” Watkins, Lisa “Left Eye” Lopes and Rozonda “Chilli” Thomas, had been showing up to award shows for years in matching looks and their black leather/mesh ensemble was no exception.

JAY-Z at the 15th Annual Soul Train Awards in 2001


JAY-Z, né Shawn Carter, was making himself known in the fashion scene before he joined forces with wife Beyoncé as an It couple. He came to the 2001 Soul Train Awards dripped out in a denim jacket and plain white tee, both baggy and oversize, which came to be a marker of JAY-Z’s style in the early aughts.

Kanye West with the Drop Out Bear in 2004

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In a now iconic image, a young Kanye West posed with a bear mascot in a Ralph Lauren orange and blue striped polo shirt during his College Dropout album cover photo shoot. The bear, according to Complex, was not a premeditated plan but came to be iconic as West dressed up in the mascot’s costume for the album’s cover and his striped shirt with the green striped button-down shirt peeking out from underneath is now forever associated with this era. His elder daughter, North, even recreated the look during a recent Japan trip.

Nicki Minaj at the 54th Annual Grammy Awards in 2012

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While Nicki Minaj was still on the rise in the early aughts, she made her mark in 2012 at the Grammy Awards and cemented herself as a fashion icon in hip-hop. She came to the red carpet with a man dressed as the Pope by her side as she wore a red Versace cape with black beaded embroidery and a blonde wig.

Migos at the 2018 Met Gala

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Migos, comprising of Offset, Quavo and Takeoff, showed up on theme in Versace to the 2018 Met Gala where the dress code abided by the Heavenly Bodies: Fashion & The Catholic Imagination new exhibit. Though each had their own distinct suit jacket, their looks were cohesive and each were dripped out in their own chains.

Cardi B at the 61st Annual Grammy Awards in 2019

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The “WAP” rapper gave “Birth of Venus” energy on the red carpet at the 2019 Grammy Awards in her Mugler haute couture gown — which was later displayed in a museum. The dress made it appear as though Cardi B were coming out of a shell, much like the myth of the goddess Venus, who was born from sea foam.

Tyler, The Creator at the 62nd Annual Grammy Awards in 2020

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Tyler, The Creator is known for always doing something unique with his look and he delivered just that at the 2020 Grammy Awards. Showing up in a Golf Le Fleur bellhop cap and outfit, complete with white gloves and a suitcase, the rapper played the part on the red carpet, giving a very Wes Anderson-type of feel and bringing something new.

A$AP Rocky at the 2021 Met Gala

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A$AP Rocky, known in hip-hop as “Pretty Boy Flacko,” is often lauded for his fashion-forward outfits, in addition to his rapping skills. But his 2021 Met Gala look cemented him as a style icon, whether critics liked the look or not. The ERL quilt-cape got people talking and hopefully provided the rapper with a cozy feel for the night.

Rihanna at the Fenty Beauty Universe Event in 2022

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The Diamonds singer is just as infamous for her iconic style as her piercing vocals, but her pregnancy looks took her fashion game to the next level. With every look, she showcased her growing belly, and fans went wild. For this outfit from her event celebrating her brand Fenty Beauty in February 2022, Rihanna wore an ensemble by The Attico which included a backless shredded shirt and pink shredded pants.

Doja Cat at the Schiaparelli Haute Couture Spring Summer 2023 show

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Doja Cat may have been an audience member at Schiaparelli haute couture spring summer 2023 show, but she was the center of attention in online discourse for her head-to-toe red outfit. The Woman singer was covered in red paint and wore 30,000 Swarovski crystals complete with boots that resembled “men’s toes,” as Doja Cat told Vogue France as she got ready.

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