April 21, 2024

The 25 Best Dressed Rappers of All Time

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Missy Elliott

Missy Elliott attends the Yellow Ball, hosted by American Express and Pharrell Williams, at the Brooklyn Museum on September 10, 2018 on September 10, 2018 in New York, New York. Photo by Kevin Mazur/Getty Images for American Express

Since the beginning of hip-hop culture, fashion has been the unofficial sixth element — from early rappers like Eric B. and Rakim and Salt-N-Pepa shopping at Dapper Dan’s 24/7 Harlem boutique to MC Shan and LL COOL J copping spray-painted sweatshirts from pioneering streetwear brand the Mighty Shirt Kings at the Jamaica Colosseum Mall in Queens. Whether you call it getting dipped, fresh to def, fly, bangin’, dope, jiggy, or lit, it has always been about being original and standing out from the crowd. In honor of hip-hop fashion and its impact on fashion overall, we’ve decided to rank the best dressed rappers of all time.

Our criteria is as follows: originality and confidence, attention to detail (jewelry, footwear, hats, sunglasses, and handbags), memorable fashion moments (music videos and red carpet appearances, for example), grooming (hair, makeup), fashion contribution (trendsetter, fashion endorsements, or own fashion label), as well as era/time period. Here are the 25 best dressed rappers of all time.

25. Migos

Migos

Migos attends the Heavenly Bodies: Fashion & The Catholic Imagination Costume Institute Gala at The Metropolitan Museum of Art on May 7, 2018 in New York City. Photo by Neilson Barnard/Getty Images

Claim to fame: Versace, Dolce & Gabbana, Prada, motocross-inspired jackets, ice jewelry

The Atlanta rap trio, composed of Offset, Quavo and the late Takeoff, rep hard for the South, putting Southern swag on the map whether it‘s streetwear or high-end. These “Bad and Boujee” trendsetters have worn everything from Versace at the Met Gala and Prada on tour to Offset walking on the Parisian catwalk. Migos have continued to expand their fashion palette since breaking out with their hit song “Versace” in 2013.

24. Kwame

Kwamé

Rapper Kwamé performs at the Mecca Arena in Milwaukee, Wisconsin in June 1989. Photo By Raymond Boyd/Getty Images

Claim to fame: high-top fade, hair dye, cane, and polka dots

Queens rapper, songwriter, and producer Kwame Holland will go down in history as the guy who put polka dots on the map. At 16, he emerged on the scene in 1989 with the classic hip-hop album, The Boy Genius: Featuring a new Beginning. But it would be his signature style of polka dot gear in music videos that sparked one of hip-hop’s earliest fashion trends. From rocking a full polka dot suit in “The Rhythm” to orchestrating a polka dot album cover for the 1990 album A Day in the Life: Polkadelick Adventure, Kwame’s polka dot era was such a standout that even the late Biggie Smalls referenced it (albeit derisively) on his “Unbelievable” track.

23. Slick Rick

Slick Rick

Slick Rick performs onstage during #TBT Night Presented By BuzzFeed at Mastercard House on January 25, 2018 in New York City. Photo by Christopher Polk/Getty Images for Mastercard

Claim to fame: King of hip-hop bling, eyepatch (often encrusted in diamonds or made to match his gear), thick double rope chain, customized Clark Wallabees, king’s crown and regal cape

Although all members of the Get Fresh Crew offered their own distinct form of Harlem fly, there’s no denying that Slick Rick was the standout. The “La Di Da Di” rapper made wearing Ballys, Kangols, and Clarks cool, the latter of which became an integral part of his personal style. Often playing with color — both pastels and vibrant color palettes — and accessorizing himself with as much bling as his body could handle, Slick was an early fashion figure in hip-hop, his wardrobes just as eccentric as his vocals.

22. JAY-Z

JAY-Z

JAY-Z performing at Sprite Liquid Mix Tour 2002 at Shoreline Amphitheater in Mountain View CA on September 8th, 2002. Photo by Tim Mosenfelder/Corbis-Sygma

Claim to fame: Rocawear, Reebok S. Carters, G-Star, Tom Ford, Mitchell & Ness throwback jerseys, Yankee fitteds, Hublot and Audemars Piguet watches

A fashion maven, JAY-Z’s versatile style can easily go from throwback jerseys to an on point suit at a moment’s notice. As he declared on “What More Can I Say”: “And I don’t wear jerseys / I’m thirty-plus / Gimme a crisp pair of jeans, nigga, button-ups.” But there’s also the fact that the artist once had his own clothing brand, too. In 1999, he launched Rocawear with then music partner Damon Dash. An extension of Roc-a-Fella, he tapped into his already existing loyal fan base with Rocawear, which helped the brand become a global seven-figure business with mens and womens fashion.

21. Lil Wayne

Lil Wayne

Lil Wayne onstage during the 2012 MTV Video Music Awards at Staples Center on September 6, 2012 in Los Angeles, California. Photo by Christopher Polk/Getty Images

Claim to fame: bling, jeggings, bandanas, Bathing Ape

Lil Wayne is well known for his eclectic fashion as a member of the Hot Boyz. He put the 2000s on the map by rocking everything from skate to street luxe, wearing brands like Bathing Ape, B.B. Simon Belt, and Louis Vuitton (especially their much-adored belts). Classic Weezy has always consisted of a mix assortment of casual and flashy – from basic tees and bandanas to print-colored animal-printed leggings paired with extravagant ice chains and jewelry.

20. Salt-N-Pepa

Salt-N-Pepa

Photo of Salt n Pepa. Photo by Michael Ochs Archives/Getty Images

Claim to fame: “Push It” jackets, spandex bodysuits, leather boots, Reebok 5411s, distressed jeans, Afrocentric accents, big hats, and mushroom cut hair styles

Salt-N-Pepa brought a mix of feminine flair and sexiness to the hip-hop game, as they broke away from traditional androgynous fashion seen by female rappers of their time. These leading ladies were on the cutting edge of fashion, donning spandex body suits over Dapper Dan leather jackets, Afrocentric styles, and distressed ripped jeans with Reebok 5411s. The group also brought platinum blonde hair hairstyles to the scene, and made mushroom cuts very fashionable in the mid-‘80s.

19. Big Daddy Kane

Big Daddy Kane

American rapper and actor Big Daddy Kane, circa 1988. Photo by Michael Ochs Archives/Getty Images

Claim to fame: flat top, silk shirts, slacks, dress shoes, jewelry, Shirt King shirts, and Dapper Dan MCM outerwear

Big Daddy Kane came on the scene with a renowned sense of style and sophistication like no other in the early ‘80s. From the Bed-Stuy rapper’s flat top to his extensive rings and oversized gold rope chains, his style was the perfect combination of sartorial and street. As one of hip hop’s earliest sex symbols, the “Smooth Operator” rapper was featured butt naked in Madonna’s provocative metal-covered book Sex, alongside Naomi Campbell and the queen of pop herself.

18. Lil Nas X

Lil Nas X

Lil Nas X poses in the press room during the 2019 American Music Awards at Microsoft Theater on November 24, 2019 in Los Angeles, California. Photo by Matt Winkelmeyer/Getty Images for dcp

Claim to fame: all neon-green outfit, Moschino shiny purple suit, platinum crop top and metallic wide-leg trousers

Breaking onto the scene with his hit “Old Time Road,” Lil Nas X made his mark in the industry with hit music and flashy fashion style. Never relying on fashion rules, X has always taken the daring road to fashion. From wearing monochromatic looks in neon, fuchsia, silver, and purple to bright yellow feathered sleeve suits by Gucci, his costume choices are daring and edgy, ready to make fans and critics talk well after he’s moved on to the next outfit.

17. The Diplomats

The Diplomats

Photo by Dimitrios Kambouris/Wire Image

Claim to fame: pink fashion, bling jewelry, colored bandanas

The Diplomats (better known as Dipset) can brag about many things — including their domineering, flashy fashion style by crew members Cam’Ron, Jim Jones, Juelz Santana, Ezekiel “Freekey Zekey” Giles, and Hell Rell. Cam’Ron will forever be known as the fella who wore an all-pink fit to fashion week, his matching mink fur coat, headband, and i730 Motorola Nextel phone helping him gain the nickname, Harlem’s Pink Panther. Juelz on the other hand, makes sure to rock bandanas in a variety of colors fit for every occasion, while Frekey Zekey and Hell rell rep for uptown in everyday street attire.

16. Snoop Dogg

Snoop Dogg

Snoop Dogg performs onstage at the Aire Crown Theater, Chicago, Illinois, December 31, 2006. Photo by Paul Natkin/Getty Images

Claim to fame: Pittsburgh Penguins hockey jersey, bandana print, pinstripe gangster suits, Dickies chino pants, fedoras, mink coats, a variety of hairstyles (cornrows, afro, hair flip, ponytails)

Snoop Dogg is among the West Coast rappers whose style has been on par with their lyrics. Whether rocking head to toe chino Dickies and bandanas to pinstripe gangster suits, Snoop has proven he is a versatile dresser to fit any occasion. His hair is often another key piece of his looks, having done cornrows, a blown-out afro, hair flips, ponytails, braids and other hair styles throughout his career.

15. Nicki Minaj

Nicki Minaj

Nicki Minaj attends Heavenly Bodies: Fashion & The Catholic Imagination Costume Institute Gala at The Metropolitan Museum of Art on May 7, 2018 in New York City. Photo by Rabbani and Solimene Photography/Getty Images

Claim to fame: pink, leather, neon colors, leopard Givenchy, Moschino, Margiela catsuit, platinum hair, Met Gala ensembles

Nicki Minaj is among the most underrated female style icons. From her devotion to the color pink and platinum blonde locks to memorable Met Gala ensembles, she has proven to be a serious fashionista. Always dressed to steal the spotlight, Minaj makes daring fashion choices to accentuate her curves and sexual prowess. Unapologetically Nicki, her style is all about being bold and revealing, yet simple.

14. Tupac Shakur

Tupac Shakur

Tupac Shakur performs at the Regal Theater in Chicago, Illinois in March 1994. Photo By Raymond Boyd/Getty Images

Claim to fame: Karl Kani, Versace silk shirts, workwear, double-breasted suits

In the ‘90s, the late Tupac Shakur had versatility in his wardrobe choices, spanning everything from Black-owned denim brand Karl Kani (a la Poetic Justice) to Italian fashion house Versace. One particular standout outfit Tupac donned during his career was a double breasted suit with wing-tipped collars and a gold chain, which he wore for red-carpet events like the Grammys and AMA awards. 2Pac’s sartorial style choices ran deep just like his lyrics.

13. A$AP Rocky

A$AP Rocky

Asap Rocky attends LACMA Art + Film Gala 2018 at Los Angeles County Museum of Art on November 3, 2018 in Los Angeles, CA. Photo by David Crotty/Patrick McMullan via Getty Images

Claim to fame: designer labels from Bape to Fendi, print campaigns for Tommy Hilfiger, Gucci, and Calvin Klein

A$AP Rocky represents the perfect combination of high fashion meets streetwear. A fashion connoisseur who’s never afraid to take risks, he gravitates to a wide variety of styles, colors, and brands. His quintessential style encompasses fitted blazers, leather jackets, and Saint Laurent teddy jackets.

12. Sean “Love” Combs

Sean Combs

Sean Combs at the Finish Line Garden State Plaza in Paramus, New Jersey. Photo by Johnny Nunez/WireImage

Claim to fame: All-white Hamptons parties, easy transitions from baggy to tailored suits, Sean John, first African-American designer to win a Council of Fashion Designers of America (CFDA) Award

Always keeping a clean cut image, Sean “Love” Combs’ wardrobe has always been versatile, spanning everything from velours and pinstriped suits to an all-white tuxedo for a red carpet affair (and often accentuating these looks with an overcoat or fur). But the entrepreneur has also received some of fashion’s highest honors, too, having earned the CFDA’s Menswear of the Year award in 2004 for his work through Sean John. Previously nominated four times by the CFDA for the award, when Combs won he beat out Ralph Lauren and Michael Kors, becoming the first Black designer to receive the honor. It’s also worth noting that Sean John was the first brand to ever have its runway show simulcast nationally, adding to Combs’ fashion impact. 

11. Tyler, the Creator

Tyler, the Creator

Tyler The Creator attends the Kenzo Fall/Winter 2022/2023 show as part of Paris Fashion Week on January 23, 2022 in Paris, France. Photo by Stephane Cardinale – Corbis/Corbis via Getty Images

Claim to fame: Supreme, GOLF, pushing the color pink, pastels, patterns, skater style, vests, accessories

Tyler, The Creator exemplifies everything cool. From his personal style to the creation of his own brand GOLF, his eclectic style has evolved much like his music. Unconventional is an understatement for the artist. He’s made pink Chanel bags popular, experimented with skater-inspired designer looks and, more recently, elevated his style by incorporating tailored clothing and designer brands. But a crucial part of his impact lies in how his past skater-style aesthetic practically became a defining wardrobe for the blog era. You can’t think of that time without remembering Tyler’s affinity for Supreme, or seeing his own Golf Wang brand become the uniform of choice for teens and young adults during the early to mid-2010s. He’s even had collabs like the one he did with Converse sell out in a day. Having branched out into nail polish and fragrances through le FLEUR, Tyler continues to be a defining figure in hip-hop fashion.

10. Doja Cat

Doja Cat

Doja Cat arrives for the 65th Annual Grammy Awards at the Crypto.com Arena in Los Angeles on February 5, 2023. Photo by Robyn BECK/AFP via Getty Images

Claim to fame: sculptured ensembles, Schiaparelli muse, Thom Browne “worm” outfit

Doja Cat has evolved into a daring hip-hop fashion darling who is never afraid to go outside the box of what is expected of her. From glam and edgy to timeless and outrageous, Doja Cat knows how to keep all eyes on her. Whether it’s covering herself in 30,000 red Swarovski crystals while wearing a Schiaparelli dress for Paris Fashion Week to oddly donning a “worm-like” dress by Thom Brown (inspired by The Little Mermaid), Doja Cat is all about standing out and being noticed.

9. Cardi B

Cardi B best dressed

Cardi B attends The 2019 Met Gala Celebrating Camp: Notes on Fashion at Metropolitan Museum of Art on May 06, 2019 in New York City. Photo by Dimitrios Kambouris/Getty Images for The Met Museum/Vogue

Claim to fame: red anything (clothes to red-bottom shoes), anything vintage from Thierry Mugler, most-talked about outfits in Paris for Fashion Week, Met Gala red carpet moments, designer looks from Moschino, Schiaparelli and more

Cardi B knows how to make a fashion statement. The rapper has become an instant cultural phenomenon who has carefully crafted her image and career trajectory thanks to her partner in fashion, celebrity stylist Kollin Carter. From sequins and animal prints to vintage styles from Thierry Mugler, Cardi continues to push boundaries between unconventional and traditional fashion. Among her most fashionable moments: her studded-spiked outfit from Richard Quinn during Paris Fashion Week (2021),  a red feathered fantasy gown from Thierry Mugler’s 1990s archives for the Couturissime Museum exhibit opening (2021),  vintage Thierry Mugler for the 61st annual Grammy Awards (2019), her aqua ball gown Rihanna’s Diamond Ball (2017), and Thom Browne’s red gown to the Met Gala celebrating Camp (2019). From street to couture, Cardi is among the most fashionable hip-hop figures to date.

8. LL COOL J

LL COOL J best dressed

LL Cool J on 7/2/87 in Chicago, Il. Photo by Paul Natkin/Getty Images

Claim to fame: Kangol hats, tracksuits from Kappa, Troop, and Le Coq Sportif, FUBU spokesperson

When we think of style mavens, LL COOL J has held the title for several decades. The epitome of cool, LL has many styles that are associated with him. From red bucket Kangols to custom spray to one-of-a-kind outfits made by Dapper Dan, the rapper has always stood out. Track suits from brands like Troop, Kappa and Le Coq Sportif were also an early favorite of his, often wearing them with dookie chains and multi-fingered rings throughout the ‘80s and ‘90s. And how could we forget his sly promo of FUBU in a Gap commercial? Paired with his chiseled body and dimples, LL’s fashion sense is a part of why the Ladies Love Cool James — then and always.

7. Run-D.M.C.

Run-D.M.C. best dressed

Joseph Simmons, Darryl McDaniels and Jam Master Jay of the hip-hop group “Run DMC” pose for a portrait session wearing Addidas sweat suits in front of the Empire State Building in May 1985 in New York, New York. Photo by Michael Ochs Archives/Getty Images

Claim to fame: shell-toe and Adidas tracksuits, leather, Cazal glasses, gold rope chains, fedora hats, first rap group (non-athlete) to sign $1 million endorsement deal with Adidas

Run-D.M.C. brought “new school” rap to the scene, and streetwear center stage. Once known to perform at Sal Abbatiello’s legendary Bronx night club Disco Fever in plaid sport jackets, the Queens rap trio inevitably embraced athletic wear as their signature look. Adidas became their brand of choice, with the group wearing tracksuits and footwear from the sportswear manufacturer. This all came to a head with their song “My Adidas,” resulting in Adidas’ unlaced shell-toe shoe becoming a part of hip-hop history, as well as landing Run-D.M.C. a million-dollar endorsement deal (the first of its kind for a rap group).

6. Wu-Tang Clan

Wu-Tang Clan best dressed

U-God, Method Man, Raekwon, GZA, Ghostface Killah, Masta Killa, RZA, Ol’ Dirty Bastard of the Wu-Tang Clan pose for a portrait circa April, 1997 in New York, New York. Photo by Bob Berg/Getty Images

Claim to fame: Polo Ralph Lauren, Avirex leather jackets, Wu Wear apparel brand and retail shops, Wu logo on Crocs to Wallabees

Raekwon made the Ralph Lauren Snow Beach pullover jacket famous in the “Can It All Be So Simple” video, while Ghostface Killah put Clarks on the map. RZA has always been a fan of bandanas, and the late ODB was known for his wild braids. Each represented the environment they were in, and created memorable looks onstage and in music videos. But what really cements the Wu as an impactful force on fashion is its instantly recognizable logo. The Wu logo has become one of hip-hop’s most beloved and ubiquitous logos, appearing on everything from sweatshirts to Crocs. Oliver “Power” Grant capitalized on the Wu brand and the group’s international success when he created Wu Wear. Along with having a flagship store in Staten Island, there were Wu Wear shops in Philadelphia, Atlanta, and Virginia Beach, Virginia. The brand was even sold at Macy’s 34th street for some time in the ‘90s.

5. Andre 3000

Andre 3000 best dressed

Andre 3000 of OutKast during 12th Annual Elton John AIDS Foundation Oscar Party Co-hosted by In Style – Inside at Pearl in West Hollywood, California, United States. Photo by L. Cohen/WireImage

Claim to fame: preppy, pearls, pink, hipster, dresses, big and wide-brimmed hats

Daring, bold, trendsetter, and outrageous are just a handful of adjectives to describe Andre 3000 and his immaculate sense of style. The Outkast rapper has come a long way from his early days of the throwback jersey craze of the 2000s. Since then, he’s developed an unconventional style unconcerned with labels, wearing everything from a dress for Outkast’s Stankonia promo pictures to jumpsuits with political slogans for Outkast’s 2014 tour.

4. Lil Kim

Lil Kim best dressed

Lil Kim wearing a revealing, purple-sequined dress with pasties, waves to the camera at the MTV Video Music Awards at the Metropolitan Opera House at Lincoln Center, New York City. Photo by Karl Feile/Hulton Archive/Getty Images

Claim to fame: sex appeal, high fashion (Giorgio Armani, Fendi, Gucci, Dapper Dan), fashion muse for Donatella Versace and Marc Jacobs, pink admiration, colored wigs and furs, lavender jumpsuit

There’s no denying Lil Kim’s impact when it comes to female hip-hop fashion. Iconic moments from the rap queen include her 1999 VMA Awards lavender jumpsuit (with the exposed breast and pastie on her nipple), and her The Wiz-inspired monochromatic head-to-toe looks (from wigs to furs) for the “Crush on You” video, both of which were created by celebrity stylist Misa Hylton. Never afraid to push the envelope, Kim has promoted colors like pink and neon, as well as avant-garde fashion to cement her style legacy. With over 20 years in the game, Kim’s sex appeal, high fashion taste, and iconic fashion moments secured her place in fashion history, paving the way for future hip-hop fashionistas.

3. Pharrell Williams

Pharrell Williams best dressed

Pharrell Williams during Pharrell Williams and Absolut Ruby Red Host Pre VMA Party – Outside Arrivals at Chinatown Brasserie in New York City, New York, United States. Photo by James Devaney/WireImage

Claim to fame: newly named men’s creative director at Louis Vuitton, long history of fashion collabs with brands including Tiffany & Co., Moncler and Adidas, Billionaire Boys Club/Ice Cream brand

Pharrell Williams was recently named the creative director of Louis Vuitton, replacing the late Virgil Abloh, the first Black creative director of the brand. Williams is no stranger to the world of fashion and can easily sport streetwear, luxury, couture, and ready-to-wear. There are no rules or boundaries when it comes to Williams’ styling choices. They are eclectic and genderless as he easily takes fashion cues from mens and womens clothes. He can rock Bape just as easily as he does Celine or Chanel. He’s had a long history of collaborations with brands like Comme des Garcons, Moynat, Colette, and Tiffany & Co. He’s also had his hand at entrepreneurship, launching his own brands — Billionaire Boys Club/Ice Cream — that everyone from Lil Wayne and JAY-Z have worn.

2. Missy Elliott

Missy Elliott

Missy Elliott performs at Lilith Fair at Jones Beach, New York, New York, July 16, 1998. Photo by Steve Eichner/Getty Images

Claim to fame: finger waves, bubblegum pink Adidas and Kangol outfit, tracksuits, Nike AirForce Ones, bedazzled denim, Dior, multitude of stylish music videos

Missy Elliott has always had an eye for fashion, and her personal style as well as her music videos are living proof. Her credits for fashionable music videos span across decades — from the the instantly memorable trash bag look of “The Rain (Supa Dupa Fly)” and the fly Maroon Adidas tracksuit from “Gossip Folks” to the dystopian, reflective silver hoodie in “WTF (Where They From)” and the edgy black leather jumpsuit from “I’m Better” — with the rapper using these videos to showcase her distinct fashion eye. Let’s also not forget that she’s the one who partially-inspired Misa Hylton’s iconic lavender jumpsuit that Lil Kim wore at the 1999 VMA Awards, adding to the undeniable fact that Missy’s creativity and ingenuity isn’t just reserved for her music, but her ideas of fashion, too.

1. Kanye West

Kanye West

Kanye West performs onstage as Samsung Galaxy Presents JAY-Z and Kanye West At SXSW 2014 on March 12, 2014 in Austin, Texas. Photo by Rick Gern/Getty Images for Samsung

Claim to fame: Ralph Lauren pink polos and bear sweaters, Margiela mask, Raf Simons camouflage jacket, Rick Owens, leather Givenchy kilt, sneaker collaborations with A Bathing Ape, Nike, and Adidas, Yeezy

There is no doubt that Ye, formerly known as Kanye West, is one of the most influential rap figures in fashion. We’ve seen his personal style choices evolve: Ralph Lauren pink polos in 2004; a Givenchy leather kilt for the “12-12-12” Sandy benefit concert in 2012; and the Margiela face mask for his Yeezus Tour in 2013 (to name a few). Early in his career we saw how he wanted to conquer fashion — not just as a trendsetter but as a legitimate designer — and he absolutely did. From helping resurrect the Gap brand to becoming the billion-dollar man behind the mega successful Yeezy line, Ye has proven that he is a fashion force to be reckoned with. Despite his multitude of Freudian slips, like him or hate him, no one compares.

Elena Romero is a fashion journalist and Assistant Chair, Marketing Communications, at the Fashion Institute of Technology in New York City. She is the co-editor of Fresh, Fly, Fabulous: 50 Years of Hip Hop Style and author of Freestylin’: How Hip Hop Changed the Fashion Industry. She is also co-curator of the “Fresh Fly Fabulous: 50 Years of Hip Hop Style” currently on display at the Museum at FIT until April 2023.



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