Hip Hop’s Trendsetters: The 10 Most Stylish Rappers
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Tyler the Creator and Pharrell Williams Most Stylish Rappers
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Hip Hop and fashion have been intertwined since the genre’s inception, with many rappers doubling as trendsetters. The relationship between the two is symbiotic: Brands gain cultural significance and reach new audiences through endorsements, while artists use their wardrobes to communicate their personas. As a result, fans will often see rappers launching their own clothing lines, teaming up with designers for capsule collections, and even dictating streetwear trends globally.
Rap-Up rounded up a list of 10 stylish rappers whose impact on music and fashion is undeniable. Whether it’s artists who’ve forayed into design like Kanye West or the well-documented fashion evolution of Cardi B, today’s visionaries are certain to inspire future generations to come. Check them out below.
1. Cardi B
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“Moodboard, all y’all imitatin’ my style,” Cardi B declared on 2024’s “Like What (Freestyle).” To some extent, she’s correct. The New York native’s style evolution is something that simply can’t be ignored, especially considering she went from repping Fashion Nova to turning heads at Paris Fashion Week in the span of a few years.
Cardi’s Met Gala and award show looks are equally impressive. During the annual fashion exhibit’s 2018 event, she walked the red carpet covered in jewels from head to toe, courtesy of Moschino designer Jeremy Scott. Meanwhile, in 2023, she paid homage to Karl Lagerfeld in a white-and-black floral ballgown — one of four looks she debuted that evening.
2. ASAP Rocky
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ASAP Rocky has landed on “best-dressed rappers” lists year after year, and for good reason. He’s contributed to a number of standout moments in fashion. Take his 2023 Met Gala appearance — which, let’s be honest, not many male rappers can pull off a plaid skirt – for example. Or, his “Peso” video, which saw him wearing Jeremy Scott x Adidas sneakers with a Supreme leopard-print towel.
Rocky worked with the New York-based streetwear label on several occasions, as well as brands like Raf Simmons, GUESS, and PUMA. During an interview with “Drink Champs,” the “L$D” hitmaker revealed that he’s “ghost designed” for a few fashion houses: “We’ve been doing that for eight, nine years now.”
3. Doja Cat
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These days, everything Doja Cat does is a career highlight. She’s come a long way from her pop roots, for better or worse. While much of the world was introduced to her via songs like “Mooo!” and “Say So,” her Planet Her era introduced the breathtaking, sometimes NSFW rapper we know today.
Fans began recognizing Doja as a style icon shortly after her dynamic debut at Paris Fashion Week in 2022. “My Fashion Week experience was special because I was able to get the message across to people that I am an explorer of art and fashion,” she explained to W Magazine. While attending Schiaparelli’s Spring/Summer 2023 show, the artist was covered head to toe in 30,000 red Swarovski crystals, a look created by makeup artist Pat McGrath.
Fast-forward to 2024, and Doja has had some pretty bizarre fashion moments. While shopping for diamonds in New York, the rapper styled a bed sheet as a dress. Very few would’ve predicted it was a teaser for her second Met Gala, where she wore an oversized white tee drenched in water.
4. Lil Uzi Vert
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Taking inspiration from Young Thug, Philadelphia star Lil Uzi Vert has a relatively fluid approach to fashion. When they first emerged onto the scene, their style — and that of fellow SoundCloud-era rapper Playboi Carti — consisted of graphic tees, jewelry, and tons of VLONE and Off-White. Throughout the years, we’ve seen their style grow to be a bit more mature while still paying attention to the tiny details. They’re no stranger to controversial fashion moments either.
The “Money Longer” hitmaker wore a red crop top with lifted shoulder pads and a Chrome Hearts Birkin bag during their set at Coachella 2024, which sparked a few side eyes from arguably less-fashionable peers. As polarizing as Uzi’s looks can be for some, their style is always ahead of its time.
“Honestly, in my heart, I think I do [fashion] better than music,” Uzi said in a feature for GQ. “You’re like, ‘Wait a minute. You’re telling me I can’t buy all this stuff out the store, I have to get archival stuff?’ Oh, s**t! I’m losing. I’m not losing anymore, though.”
5. Kanye West
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Kanye West Most Stylish Rappers
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When it comes to fashion, Kanye West’s influence is undoubtedly seen in everyone from his protégées, such as Travis Scott and Big Sean, to his ex-wife, Kim Kardashian, whose SKIMS he “ghost creative directed.” During his The College Dropout era, the Chicago rapper wore “the backpack with the Polo and the first Jesus piece.” Since then, his style has taken on many, many life forms: leather slacks and fur coats in 2011, Chelsea boots and jeans later, and the earthy tones found across early Yeezy Season launches.
Speaking of Ye’s Yeezy brand, it’s iconic in itself. From the label’s sneaker releases to its billion-dollar partnership with Adidas, fashion has proven to be just as much of a vehicle for self-expression as music is for the Grammy winner. In more recent times, face masks, all-black fits, and interesting silhouettes have all characterized the artist’s style.
6. JT
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City Girls cemented themselves as a powerhouse in Hip Hop, but when it comes to fashion, JT really takes the cake. The “OKAY” artist fronted POSTER GIRL’s Autumn/Winter 2023 collection in a blue jumpsuit and red latex dress, among other outfits. It was the start of something great.
During the 2023 BET Awards, she wore a corseted suit and tulle skirt from Jean Paul Gaultier’s fall 2022 collection, while the visuals for “Sideways” saw her in a coat from Bottega Veneta’s 2017 ready-to-wear collection. As if that wasn’t enough to solidify her as an authority in fashion, JT partnered with De’arra Taylor’s eyewear brand, Lorvae.
7. Tyler, The Creator
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Once synonymous with the skate culture aesthetics of his Odd Future days, Tyler, the Creator has evolved both musically and stylistically since breaking into the mainstream. During the early 2010s, the California native was pivotal in popularizing brands like Supreme and Vans, among others. His frequent use of the former label’s iconic blue box logo hoodie and five-panel caps in music videos like “She” and “Oldie” made Supreme a staple in youth fashion.
As his artistic direction matured, so did his fashion sense. Tyler launched his own clothing line, GOLF WANG, which he wore exclusively for years, signaling a shift from his earlier skate-inspired, rebellious aesthetic to a more defined and personal brand identity. Meanwhile, in 2024, the IGOR creator debuted a capsule collection with Louis Vuitton, marking his first collaborative effort with a luxury fashion house.
8. Doechii
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Doechii Most Stylish Rappers
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Doechii’s achievements have certainly stacked up since her breakout year. The viral success of “What It Is (Block Boy),” coupled with an opening slot for Beyoncé’s “RENAISSANCE WORLD TOUR” and BET Awards performance, underscore the Florida-born rapper’s rise to acclaim. Beyond music, Doechii is quickly becoming one of fashion’s it-girls, treading a similar line as the likes of JT, Aliyah’s Interlude, and Doja Cat.
Her single “Yucky Blucky Fruitcake” is a great representation of her love for fashion: “In my black Taylor Chucks, the ones that laced up to my thighs / Lisa Frank lipstick on my eyes / Weird girl activity, Black b**ch nativity / Spy girl erotica, bucket hat from Nautica.”
9. Pharrell
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Pharrell Williams Most Stylish Rappers
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Pharrell Williams has long been regarded as a fashion pioneer. He was one of the early adopters of A Bathing Ape — worn by the likes of Kanye West, Big Sean, and Lil Wayne — and his partnerships with founder and designer Nigo led to the creation of mainstay streetwear lines like Billionaire Boys Club and IceCream. Even in the early 2000s, as part of N.E.R.D., Williams collaborated with labels like Nike and BAPE, paving the way for his later partnership with Adidas, which produced original sneakers like the NMD Hu.
The beatmaker and designer’s foray into high fashion continued with the launch of a Chanel collection in 2019, which reimagined the Maison’s logos with graffiti and embellished motifs. In 2023, Louis Vuitton appointed Williams as the creative director of menswear, marking the brand’s first since Virgil Abloh’s unfortunate passing. The Virginia native debuted his initial collection that June, with plenty of support coming from both style enthusiasts and Hip Hop fans.
10. Coi Leray
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Coi Leray Most Stylish Rappers
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Since 2018’s “Huddy,” Coi Leray has quickly ascended in both music and fashion. In addition to becoming a Fashion Week regular, the New Jersey rapper made her runway debut for The Blonds in 2022. She’s also served up a number of iconic looks across her music videos, namely “Anxiety,” “Isabel Marant,” and her Hot 100 Top 10 debut “Players.”
For the BET Hip Hop Awards in 2023, the musician wore a pink and purple AREA skirt set with crystal embroideries. She paired the look with blue finger waves.
