Hip-hop is renowned for its genre-defining beats and legends, from Tupac Shakur to JAY-Z, but it’s equally celebrated for the iconic moments these artists have contributed to fashion history.

As hip-hop marks its 50th anniversary, we’ve rounded up 16 of the most memorable style moments worn by titans of the industry. This genre, deeply intertwined with fashion, features artists who stand out not just for their music, but also for their distinctive style.

From Salt-N-Pepa to Doja Cat, here are 16 iconic fashion moments in hip-hop history:

01 of 16Salt-N-Pepa in Their “Push It” Jackets (1988)In what have now become iconic outfits, Salt-N-Pepa — rappers Sandra “Pepa” Denton, Cheryl “Salt” James, and DJ Spinderella — wore jackets emblazoned with phrases like “Idol Maker” and “Let There Be Music” and images such as comedy and tragedy masks and the Salt-N-Pepa logo for their “Push It” music video. This look has become synonymous with the group and is still recreated today, even as a Halloween costume.

02 of 16Queen Latifah in 1990Queen Latifah embraced her heritage from the beginning of her career, proudly donning a colorful kufi and matching outfit with statement gold earrings. As one of the pioneering female rappers, she set the stage for many to follow, even after she transitioned into a Hollywood career.

03 of 16Tupac Shakur at Club USA (1994)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. Attending a party for the cowboy noir thriller *Red Rock West*, Tupac showed up in his best wild west attire, wearing his signature bandana, a brown leather vest, a plaid button-down, and baggy jeans. He accessorized with a gold chain featuring a cross.

04 of 16Missy Elliott at the Lilith Fair at Jones Beach (1994)Missy Elliott performed at the 1994 Lilith Fair, a music festival promoting wоmen empowerment, in a black leather blоw-up suit that resembled a garbage bag. When asked why, she responded, “I don’t know, ’cause I’m Missy.” Elliott rejected the hyper-sexualized costumes that were the norm for female stars, focusing the audience on her skills instead.

05 of 16The Notorious B.I.G. Outside His Mother’s House in Brooklyn (1995)**As one of the most legendary hip-hop artists, Biggie Smalls made waves in the fashion industry with his signature paperboy hats. In this January 1995 moment, just two years before his deаth at 24, Biggie is seen donning a leather jacket and a jersey while rolling a cigar outside his mother’s home in Brooklyn, New York.

06 of 16Lauryn Hill in 1998Recognized as one of the most influential figures in hip-hop, Lauryn Hill released *The Miseducation of Lauryn Hill* in 1998, accompanied by promotional images like this one. Hill’s outfit, featuring a purple vest sweater paired with a mesh skirt, strappy sandals, big hoops, and a choker, embraced late ’90s fashion and showcased her unique style.

07 of 16TLC at the 1999 MTV Video Music AwardsTLC, the girl group of the moment, showed up at the 1999 VMAs in matching outfits as they took home the Moonman for best group music video for their Һit “No Scrubs.” Tionne “T-Boz” Watkins, Lisa “Left Eye” Lopes, and Rozonda “Chilli” Thomas had been making statements at award shows for years with their coordinated looks, and their black leather/mesh ensemble was no exception.

08 of 16JAY-Z at the 15th Annual Soul Train Awards (2001)JAY-Z, born Shawn Carter, was already making a nаme for himself in the fashion scene before becoming half of an It couple with Beyoncé. At the 2001 Soul Train Awards, he sported an oversized denim jacket and plain white tee, defining his early 2000s style.

09 of 16**Kanye West with the Drop Out Bear (2004)In an 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, not initially part of a premeditated plan, became iconic as West dressed up in the mascot’s costume for the album’s cover. His striped shirt with a green-striped button-down shirt peeking out from underneath is forever associated with this era. His daughter, North, even recreated the look on a recent trip to Japan.

10 of 16Nicki Minaj at the 54th Annual Grammy Awards (2012)While Nicki Minaj was on the rise in the early 2010s, she made her mark at the 2012 Grammy Awards, cementing herself as a fashion icon in hip-hop. She arrived on the red carpet with a man dressed as the Pope and wore a red Versace cape with black beaded embroidery and a blonde wig.

11 of 16Migos at the 2018 Met GalaMigos, comprising Offset, Quavo, and Takeoff, attended the 2018 Met Gala dressed in Versace to fit the theme “Heavenly Bodies: Fashion & The Catholic Imagination.” Each member had a distinct suit jacket, yet their cohesive looks, complemented by their own chains, made a striking impression.

12 of 16Cardi B at the 61st Annual Grammy Awards (2019)Cardi B channeled “Birth of Venus” energy on the red carpet at the 2019 Grammy Awards in a Mugler haute couture gown, which was later displayed in a museum. The dress made it appear as though Cardi B were emerging from a shell, much like the mythological goddess Venus.

13 of 16Tyler, The Creator at the 62nd Annual Grammy Awards (2020)Known for his unique style, Tyler, The Creator delivered an unforgettable look at the 2020 Grammy Awards. Dressed in a Golf Le Fleur bellhop cap and outfit, complete with white gloves and a suitcase, the rapper brought a Wes Anderson-like feel to the red carpet.

14 of 16A$AP Rocky at the 2021 Met GalaA$AP Rocky, known in hip-hop as “Pretty Boy Flacko,” often lauded for his fashion-forward outfits, cemented his style icon status with his 2021 Met Gala look. The ERL quilt-cape sparked conversation and added to his reputation as a fashion trailblazer.

15 of 16Rihanna at the Fenty Beauty Universe Event (2022)The “Diamonds” singer, infamous for her iconic style and piercing vocals, elevated her fashion game with her pregnancy looks. At her Fenty Beauty event in February 2022, Rihanna showcased her growing belly in an ensemble by The Attico, featuring a backless shredded shirt and pink shredded pants, sending fans into a frenzy.

16 of 16Doja Cat at the Schiaparelli Haute Couture Spring Summer 2023 ShowDoja Cat, despite being an audience member at the Schiaparelli haute couture spring summer 2023 show, stole the spotlight with her head-to-toe red outfit. Covered in red paint and adorned with 30,000 Swarovski crystals, Doja Cat’s look was complete with boots that resembled “me𝚗’s toes,” as she explained to Vogue France.