13 of the flyest Hip Hop groups to ever do it

Visual presentation in Hip Hop is so important because the genre has always been about more than the music. It’s a mindset, movement, and masterclass in style. Whether it’s the military-style fits of Wu-Tang Clan, the bold femininity of Salt-N-Pepa, or the Harlem flair of The Diplomats, Hip Hop’s groups have long been fly! The way these groups dressed wasn’t just about looking good — it was a love letter to their origins and a statement of identity and power. It’s no surprise that many of their iconic fits have gone down in history, setting trends and influencing generations far beyond the stage. Here are 13 of the flyest groups to ever do it, and rest in peace to the members no longer with us.

1. OutKast

André 3000 and Big Boi start off the list for blending their unique artistry and style to become one of Hip Hop’s most successful groups. The duo redefined what style could look like in Hip Hop, with fearless, genre-blurring but distinctly Southern style. From their Dandy-inspired looks to custom and eccentric out-of-the-box creations, OutKast proved they were ATLiens and put Atlanta on the Hip Hop map visually and sonically in a major way!

2. The Diplomats (Dipset)

No list of Hip Hop’s flyest groups would be complete without The Diplomats! They were a magnum opus melding of Harlem’s bold essence and style. Their early 2000s run was filled with bandannas, oversized leather jackets, and brands like Pelle Pelle and Avirex, just to name a few of the designers they helped popularize. Decades later, Dipset continues to inspire and reinvigorate Hip Hop style.

3. Run-DMC

As the kings from Queens, Run-DMC are one of the most influential groups in all of music! Known for their high energy and how they helped catapult Hip Hop into the mainstream, the group’s love of black leather jackets, fedoras, gold chains, and Adidas Superstars shifted the paradigm. As the first Hip Hop artists to intersect with fashion branding through their partnership with Adidas, Run-DMC essentially paved the way for the collaborations we see today!

4. Clipse

“Drug rap” never sounded or looked as elegant before Pusha T and No Malice, the lyrical brothers from Virginia, coined the genre. From their early days of streetwear to their evolution as Hip Hop elders, the brothers are always fly. Whether it’s their brand Play Cloths or custom Louis Vuitton courtesy of Pharrell, the duo’s style is as lethal as their bars!

5. Wu-Tang Clan

Enter the Wu Dynasty! The powerhouse group from Staten Island is in a league of its own. Boasting nine members, Wu-Tang’s flyness exuded mystique, uniformity, and grit all tied to their sacred Staten Island territory. Their style was tactical and stylish, consisting of military jackets, Carhartt, Timberlands, Wallabees, and camouflage. Although each member had their unique style, together Wu-Tang made rugged look regal, turning everyday gear into timeless emblems of raw power.

6. N.E.R.D.

The group N.E.R.D, short for No One Ever Dies, is the blueprint for alternative cool. Together Pharrell, Chad Hugo, and Shay Haley teamed up to usher in a rebellious era and style that mixed skate culture and Hip Hop sensibilities. Their look was effortless and easygoing, full of trucker hats, baggy jeans, and punk-inspired accessories. They didn’t dress to impress; they dressed to express, creating a new lane where individuality and subcultural influence collided.

7. Migos

Quavo, Offset, and Takeoff are not only cemented as one of Hip Hop’s greatest supergroups but also one of its flyest. From their boisterous logo raps on “Versace” to their elevated sleek style during their Culture III era, the Atlanta natives introduced a style all their own! Think fitted denim, printed silk shirts, and runway-ready fits mixed with iced-out chains, watches, and grills all while maintaining their masculine edge.

8. Salt-N-Pepa

The ladies of Salt-N-Pepa introduced a feisty energy and style to the rap game all their own. From bold custom leather ensembles by Dapper Dan to their elegant red carpet dresses, Salt, Pepa, and DJ Spinderella perfectly showcased all the multi-faceted styles women could achieve. Their iconic 8-ball leather jackets and colorful headwear are still being copied to this day.

9. The Fugees

Wyclef Jean, Pras, and Lauryn Hill approached their style with looks that were laid back but intentional. Their military jackets and oversized silhouettes mixed with Afrocentric natural hairstyles redefined what it meant to be cool in the ‘90s. Their fashion choices paved the way for a new age of artists to embrace cultural pride, political consciousness, and individuality, proving that style can be revolutionary and effortlessly cool simultaneously.

10. City Girls

Yung Miami and JT of the City Girls represented unapologetic confidence, femininity, and boss-level rags-to-riches luxury. From the moment they burst onto the scene with their catchy lingo and Miami pride, all eyes were on their boisterous style! From custom performance looks to logo-filled, high-end outfits, the City Girls fulfilled a lane that Hip Hop desperately missed.

11. UGK

With their fly alter egos and cool Texan demeanors, Pimp C and Bun B embodied Southern gangster and suave. Whether rocking white furs in the Houston heat with tailor-made suits and custom gator boots like Pimp C or understated streetwear looks with the flyest kicks preferred by Bun B, the duo was the ultimate tag team. UGK is the complete embodiment of TRILL!

12. DJ Jazzy Jeff & the Fresh Prince

DJ Jazzy Jeff and the Fresh Prince, aka Will Smith, brought a clean-cut style and upbeat joy to Hip Hop in the late ‘80s/early ‘90s. Their looks were colorful, carefree, and trendsetting, think flipped hats, bold prints, crisp tracksuits, and always with the newest Air Jordans on their feet. Coming from Philadelphia, and at a time when Hip Hop was growing tougher and more aggressive by the year, the duo’s music and style were a breath of fresh air.

13. Naughty By Nature

Naughty by Nature brought their rugged New Jersey flair to the masses with their unified but never-matching looks. Treach, Vin Rock, and DJ Kay Gee embodied athletic energy by wearing Nike gear, overalls, and Timberland boots, cementing their around-the-way aspirational style, which has never gone out of style. From the block to the runway, Naughty by Nature’s unapologetic authenticity still stands the test of time.

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