Hip-hop style has changed a lot over the past 25 years. From tall tees and throwback jerseys to skinnys and Rick Owens sneakers, there have been plenty of different waves that have sprouted up in plenty of different cities throughout the 21st century.
Along the way, some rappers have stood above the rest to define the uniform of their respective eras and influence how the masses get dressed. In some cases, they’ve been able to evolve and define multiple eras with their unpredictable wardrobes. But who has done it the best?
When it came to determining the ranking of the best dressed rappers of the 21st century, a few factors came into play beyond just how many amazing outfits these individuals have put on. Have they had longevity or was their time in the spotlight more concentrated? Has their style evolved over time? Have their sartorial choices sparked trends and influenced the masses? Have brands taken notice and partnered with them?
These are our picks for The 10 Best Dressed Rappers of the 21st Century. Check out our full list of the The 25 Best Dressed Celebrities of the 21st Century here.
10. Kid Cudi
Kid Cudi cut his teeth folding clothes at American Apparel and selling shirts at BAPE’s first American flagship. The combination of indie sleaze and international hype positioned Cudder as a Blog Era golden child. His skinny jeans, Baby Milo tees, and retro Jordans were the style equivalent of a Girl Talk record.
A debut mixtape with then-streetwear heavyweight 10.Deep and a record deal with Kanye West didn’t change Cudi—it influenced his partners. Streetwear embraced the martian and Yeezy started singing. As Cudi’s popularity grew, he leaned harder into his instincts and got more experimental, referencing Kurt Cobain, dressing down on red carpets, and hitting festival stages in cropped tank tops.
Cudi’s love of rock was never cosplay and his affinity for hype was never about clout. He was grunge and imaginative, vulnerable and fearless. His style never switched, it only evolved. —Ian Stonebrook
9. Lil Wayne
White tees, Girbaud jeans, and Ben Franklin bandadas dressed a teenage Lil Wayne. Platinum chains and gold grills fronted a uniform of aspirational wealth that Wayne would tinker and toy with throughout the 2000s. He coined “bling bling” and accented each staple with Tommy Hilfiger accessories or all-white Reeboks.
As his solo career took off, Wayne shed his Hot Boy branding and regional wardrobe. He’d flirt with the throwback jersey craze up the East Coast and (allegedly) bite BAPE by way of Clipse. His camo-clad fits have achieved immortal status. He’d look good doing all of it before becoming The Best Rapper Alive in rock star garb.
Wayne’s run and influence in fashion would both taper off in the 2010s. Trukfit tangents and jegging endorsements were embraced by some crowds and denounced by others. For a time, however, Wayne was sliding the scales of how D-boys dressed and rap fans shopped. Much like his mixtape favorites, Lil Wayne rarely hopped on anything first, but he almost always did it best. —Ian Stonebrook
8. Playboi Carti
After debuting with his self-titled project in 2017, Playboi Carti burrowed into his own insular world to become one of today’s hottest trendsetters. It’s been a steady ascent. The same year as his debut, he modeled for Yeezy Season 5; in 2018, he walked in Virgil Abloh’s debut show for Louis Vuitton in addition to modeling for Off-White F/W19. With each album, his world and aesthetic has mutated, and his chronically online fans follow suit. From the Rick Owens-obsessed Opium aesthetic born from the Whole Lotta Red era to channeling prime Lil Wayne for his recent MUSIC rollout with $50,000 Chrome Hearts jeans, Timberland boots, and classic BAPE camo jackets, Carti is uncompromising. He’ll mix high and low, collaborate with luxury creative directors like Matthew Williams, and even nod to Michael Jackson. Is he the dark prince of pop? Just ask the adoring fans in Jerry Stackhouse jerseys. —Antonio Johri
7. Lil Uzi Vert
Since they captivated the Soundcloud audience with purple hair and super skinny rockstar denim in the 2010s, Lil Uzi Vert has only bolstered their status as one of hip-hop’s contemporary style icons. Early in their career, rather than channeling Dipset or Jay-Z, Uzi took cues from rockers like GG Allin and Marilyn Manson. The looks were polarizing, but for every old head yelling about something “feminine,” there were dozens of teens mimicking their every move.
As Uzi’s career progressed, fame grew, and wallet inflated, the outfits got more experimental—no stylist required. They expanded beyond the rocker look that defined their early eras and dove deeper into luxury fashion. Who could forget their run of fit pics in 2019 that included everything from Nigo-era BAPE fits at the dentist office to Prada puffers on the tarmac? Remember when they were living in the Balenciaga store in 2022? How about that giant pink diamond they implanted into their forehead when they were on their extraterrestrial swag? You never quite know what you’re going to get with Uzi. They could pop out for their set looking like a Fifth Element extra, toting an ultra rare Birkin bag, or they could keep it pacific in an all-white Chrome Hearts sweatsuit. As unpredictable and unorthodox as Uzi’s wardrobe can be, they always pull it off. That’s the true mark of any well dressed individual. —Mike DeStefano
6. Lil Yachty
Lil Yachty may not wear red braids and plug a closet full of Nautica like he did in 2016, but he’s remained at the forefront of hip-hop’s style conversation ever since his “One Night” days. The best thing about Boat’s style is his versatility. One day, he can be decked out in a vintage ensemble, and the next he’s stepping out in full Bottega Veneta. He might follow that up with a day where he’s decked out in nothing but pieces from emerging designers like NYRVA or Filthy Project. And we can’t forget about the endless collection of rare sneakers and six-figure custom jewelry that accessorizes each and every look. It’s easy to see why Nike has tapped him for a couple of Air Force 1 collabs or Cactus Plant Flea Market leans on him to unveil their latest collections on Instagram.
The scope of Yachty’s outfits is so wide because of his genuine appreciation for clothes. He’s a collector at heart that seems to have no bounds as to what he might try out next. When you have that type of range, it’s not hard to become a fixture in these types of conversations. —Mike DeStefano
5. Tyler, the Creator
Growing up in close proximity to Fairfax Avenue in Los Angeles during its time as the mecca of streetwear proved to pay dividends for the ring leader of Odd Future. As he has evolved as an artist and matured as a person, Tyler, the Creator’s wardrobe has done the same. Whether he was putting an entire generation onto Supreme box logo hoodies, rocking some of the brightest T-shirts we’ve ever seen from his own brand Golf Wang, or tapping into his opulent jetsetter bag with furry ushankas and cashmere knits, he’s leaned all the way into each aesthetic. The clearly demarcated wardrobes have made it easy for his passionate fans to follow suit. The impact is so strong that even Louis Vuitton allowed him to cover their timeless luggage in pastel flowers and Airedale Terriers.
While Supreme camp caps and pleated chinos fall on opposite ends of the style spectrum, Tyler has always been able to make his outfits feel genuine through the consistent presence of bright colors and bold patterns. A Tyler outfit is unmistakable. —Mike DeStefano
4. Andre 3000
Hip-hop scholars suggest that Afrika Bambaata & The Soulsonic Force’s “Planet Rock” is the foundation of Atlanta hip-hop, despite beaming in from The Bronx. The funky, futuristic, unrestrained energy is a spiritual space that exists in every member of the Dungeon Family, and nobody embodies this better than Andre 3000.
Since rocking a reserved-yet-intentional Braves jersey and fuzzy Kangol for his “Player’s Ball” arrival in 1993, Three Stacks has taken style to spaces only visible by telescope. For 32 years, every Andre 3000 look has been experimental and unconcerned with earthly trends.
Wigs, body paint, and topless looks with metallic accents channelled Prince and offered an unreal zag when seated next to rap royalty in the early 2000s. Soon after, he’d shift sharply to the dandy attire of his Benjamin Bixby label during an era when white tees looked like nightgowns. Though the shadow of high-waisted fringe pants and spiked shoulder pads exists online, Andre can’t be traced. The spirit of his style appears in Tyler, the Creator, Young Thug, and Lil Yachty, still somewhat adapted for modern times.
On the other hand, 3000 never needed a watch to know what period he existed in or bifocals to keep tabs on his peers. Over the last decade, he has bucked even his own expectations by creating a uniform of sorts: hickory striped overalls, bright beanies, and a flute. He was, and still is, the ultimate original and his forefather’s funkiest dreams. —Ian Stonebrook
3. Pharrell
Pharrell Williams is not just one of the best dressed musicians ever, he’s calling the shots for menswear at one of the most storied luxury houses. He’s the rare talent whose transition from trendsetter to big boss is inspiring and organic. At 52 years old, he’s still striding on a 25-year run that reads like a storybook.
In the early 2000s, he made trucker hats hip-hop and skate brands boutique. An introduction to Nigo by Jacob the Jeweler took the VA native around the globe. He was a pivotal figure in introducing A Bathing Ape to America, and the launch of BBC and Ice Cream furthered his retail reach in apparel and footwear. A nod from Marc Jacobs led to Louis Vuitton’s blockbuster Millionaire shades.
Even in his self-proclaimed “dud” era, a mustached Pharrell reveled in risk. Snowboard boots, jorts, and drawn-on Timbs took a minute to catch on, paving the way for a Malcolm McLaren gesture in the form of the infamous Vivienne Westwood hat. Skateboard P was on top of the mountain again, paying unexpected homage and altering headwear for the second time.
We all know what happened next: an Adidas renaissance, Chanel collaborations, and an appointment at Louis Vuitton. In 2025, elements of every era appear in Pharrell’s timetested-yet-timeless aesthetic. It paints a clear picture of his life’s work, from N.E.R.D. to LVMH. —Ian Stonebrook
2. ASAP Rocky
The first time the world heard ASAP Rocky rap in 2011, he proclaimed himself “that pretty mothafucka” over a dreamy Ty Beats instrumental. It’d be a tough moniker for most people to live up to, but Rocky really is that handsome. He was a bonafide trendsetter out of the gate who helped define the “street goth” era, pushing labels like Black Scale and Hood By Air into the zeitgeist. The winged Jeremy Scott Adidas on his feet became grails for young fashion heads. With Rocky’s cosign, Raf Simons became a deity to them.
As his career progressed, the music became more experimental (and less frequent), and his cutting edge fashion sense persisted. In recent years, we’ve seen his fashion power manifest in the form of AWGE runway shows in Paris, viral Met Gala moments, and ongoing collaborative partnerships with brands like Ray-Ban and Puma.
Whether he’s rocking Harlem staples like Pelle Pelle leathers, championing his “dad swag” in shirts and ties from JW Anderson’s Dior, turning a courtroom arrival into a runway show, or blinding onlookers with his latest ice from Alex Moss, Rocky is still stepping with the untouchable confidence of that pretty mothafucka stepping out of a bodega with a Supreme towel draped over his head. —Mike DeStefano
1. Kanye West
Whether you come from the generation that resonates most with his pink-ass polo and fuckin’ backpack, the LRG Dead Serious hoodie he wore sittting front row at the Stella McCartney show, ripped jeans and Chelsea boots, the The Life of Pablo merch he peddled in pop-ups around the world, or the desert-toned Yeezy sweats and sneakers that have defined the better part of the past decade, chances are you have appreciated and attempted to recreate Ye’s personal style in some way, shape, or form.
Like his discography, you could probably single out any one of his style eras and make the case that it’s one of the best of the 21st century. He wasn’t just putting on amazing outfits, even though there have been hundreds that have been burned into our memories. The “Runaway” red suit. The Celine blouse at Coachella. The diamond-encrusted Balmain jacket and Fear of God jeans at the Met Gala. The leather kilts and Givenchy tees for Watch the Throne. The diamond-encrusted Balmain jacket and Fear of God jeans at the Met Gala. The list goes on.
Ye defined entire eras of fashion. The same unpredictability that has landed him in hot water numerous times throughout his storied career has informed one of the most magnetic wardrobes in celebrity history. The fact that Ye has been able to have so many culture-defining over the past 21 years makes his spot at the top of this list undeniable. —Mike DeStefano