A lot has changed in fashion over the past quarter century. Brands came and went. Pants were baggy then they were skinny, then baggy again. Brands once considered titans of the subculture known as streetwear stepped onto the runways at Paris and Milan. Signature sneakers and sportswear collaborations, once reserved for pro athletes, became major elements of the business portfolio for some of hip-hop’s biggest stars, to say nothing of other celebrities. And yet the individuals who have been at the forefront of fashion have largely remained the same.
When it came to determining the ranking of the best dressed celebrities 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 the 25 best dressed celebs of the 21st century. List below.
25. Timothée Chalamet
Timothée Chalamet started pulling looks at movie premiers since he stepped onto the scene in 2017, notably, without a stylist. He cultivated friendships with some influential designers, including Virgil Abloh and Haider Ackermann. His breakout fashion moment came at the 2019 Golden Globes, when he arrived in a custom Louis Vuitton look by Abloh featuring a glittering harness. It was a daring departure from the standard tuxedo that dominates red carpets and immediately put him on the map.
Since then, every appearance has felt intentional in crafting his style identity. Whether pairing a custom Haider Ackermann tuxedo with Converse Chucks to co-chair the 2021 Met Gala, donning matching JUUN.J suits with Zendaya on the Dune: Part Two press tour, wearing a custom pink Chrome Hearts sweatsuit for the premiere of A Complete Unknown, or rocking a vintage Raiders jacket with some True Religion jeans and a tiny Chanel bag in the streets of Paris, Chalamet has consistently balanced playfulness with polish.
Since 2024, he’s teamed up with stylist Taylor McNeill, who also worked with Kendrick Lamar. This link up feels more like a creative partnership than a traditional client-stylist relationship. Together, they’ve honed a style that’s increasingly experimental yet deeply authentic to Chalamet. His looks walk a fine line between humor, high fashion, vintage, and streetwear—a rare feat that captures why he’s become one of the most exciting dressers of his generation. —Shinnie Park
24. Kim Kardashian
In her nearly two decades in the public eye, Kim Kardashian went from behind-the-scenes stylist to billionaire fashion mogul.
The through line is SKIMS, an empire blurring the lines between shapewear and activewear via nudes tones. But her evolution is more than skin deep. Through the late 2000s, her reality television rise ramped up in the age of Instagram and the dawn of the influencer. A courtship with Kanye West—then at the peak of his powers —shifted her style from club socialite to John Galliano gowns.
Curves became couture and Fashion Week went full celeb. From fronting the biker shorts movement to unarchiving Marilyn Monroe’s infamous “JFK” dress, Kardashian’s ability as a trendsetter and provocateur grew as the world watched.
In the last decade, Kardashian has owned and inverted every element of the A-list inventory through platform and appearance, monopolizing the attention economy and flipping female beauty standards. Her family are running with the same playbook, applying pressure to algorithms and Arnaults alike. —Ian Stonebrook
23. Justin Bieber
When you are one of the biggest pop stars of the 21st century, you have to look the part too. As Justin Bieber’s career has transitioned from teen heartthrob to respected hit maker, his personal style moved with him. The first time he really made noise with his wardrobe coincided with his Purpose era in 2015, five years after his debut. With the help of Fear of God’s Jerry Lorenzo and well-executed merch that riffed on Marilyn Manson concert tees and ’90s grunge, he overhauled his image and grew up. Tattered flannels and cut-off vintage tees became his go-tos. Lately, he has leaned into a much more relaxed aesthetic, and doubled down on it with his own brand, Skylrk. Extremely baggy sweatsuits and beanies are the antithesis to his wife Hailey’s refined looks.
Befitting his stature in pop culture, he’s caught criticism for his wardrobe. Love it or hate it, it’s helped redefine the traditional pop star uniform in a way we hadn’t seen before. Sure, he may have come out of the gate with a bowl cut, metallic leather Supras, and white denim jacket. But who didn’t have an awkward tween phase? —Mike DeStefano
22. Bella Hadid
There isn’t a super model more synonymous with women’s fashion than Bella Hadid. Scroll through any fashion girl’s Pinterest mood board and you’ll almost certainly find her face — or at least one of her outfits. The model has cycled through multiple style eras, from her early “LA model off-duty” days of skinny jeans, leather jackets, and flannels tied around the waist to grabbing a New York slice in micro shorts and platform mini Uggs. She’s responsible for reviving everything from Bayonetta glasses to Adidas Sambas. Anything Hadid touches (or rather, wears) turns into gold. She’s also used her outfits to speak out boldly about current events, notably her commitment to Palestine; she even stunned in a dress made of keffiyahs from Michael and Hushi during the 2024 Cannes Film Festival.
Hadid’s style represents the cultural mood. Her ability to shift seamlessly between personal style and high fashion cements her as an era-defining icon. —Shinnie Park
21. Young Thug
Leave it to a rapper with one of the most generic monikers of all time to become one of the most electric hip-hop artists of his generation—a sincere provocateur who’s managed to translate his eccentric energy into a one-of-one personal style.
In the early 2010s, Young Thug embodied Atlanta swag: rock star-adjacent fits with skin-tight pants, snakes, and endless denim, often in bold colors like red or purple, paired with a simple white tee. But as his music evolved,so did his fashion sense. Throughout the decade, he stayed entrenched in luxury fashion, just making bolder and more experimental choices with the clothing. You think wearing a Moncler bubble coat is hard? Try pulling off a multicolored patchwork Moncler wool poncho. Each escalating outfit sparked a new conversation—a constant push and pull against the lingering boundaries of hip-hop style, even as Thug himself seemed to approach it all with the nonchalance of someone who knew he was just getting fits off.
And then there were the dresses. With leopard and checkered prints, these statement pieces made Thug an androgynous icon. There may be celebrities who dress “better” on this list, but it’s hard to name a single garment more iconic than the Jeffery dress, that lavender, flowing gown designed by Alessandro Trincone. Of course, the image was memed to death and endlessly dissected, yet it remains one of the defining fashion moments of the century, a work so stunning it earned a place at the Museum of Fine Arts in Boston. —Dimas Sanfiorenzo
20. Jim Jones
Jimmy entered the rap game with a swagger that eclipsed his accomplishments, acting as a camera magnet even when cast as a co-star. Bronx brawniness, Harlem waviness, and West Coast gang signs made him the most provocative Diplomat. He stole scenes in music videos in Blood red bandanas and pressed perms.
By the mid 2000s, Capo’s catalog caught up to his charisma by way of “We Fly High’” and Complex covers. He became a boss in his own right, departing Dipset and spreading his wings with ByrdGang. In that time “Chrome Jones” was born, trading in oversized throwbacks for fitted henleys and heavy metal accessories. New York and New Orleans both took note.
Keep in mind, this was all in 2006: nearly two decades before your favorite hooper hopped on the Chrome Hearts bandwagon or your favorite rapper “revived” Pelle Pelle. Quiet as kept, Jones’ instincts have aged better than some of his more popular peers.
An instigator on wax, an incendiary when poppin’ tags, Jones can rock Jimmy Jazz with the confidence of couture and turn Louis Vuitton scarfs into streetwear. He understands silhouette better than most stylists and moves with masculinity no matter the fad. Even when he isn’t setting the trends he’s bending them in his favor. That’s muscle. —Ian Stonebrook
19. Teyana Taylor
Teyana Taylor’s tomboy beginnings and choreography acclaim made her the first lady of Star Trak before she was old enough to drive. Talent, taste, and co-signs opened doors other It Girls couldn’t while emotion and authenticity endeared her to communities couture, contemporary, and queer.
The ability to transcend worlds and eras shaped one of the most impressively non-linear ascents fame and fashion have ever seen. Diesel runways and Adidas deals made Taylor a fixture at Fashion Week. Even if Twitter beef with Rihanna cost her a shoe deal or Ye’s lack of direction denied her musical support, it all gained her attention and even a hive.
All the while, Taylor was fly and flawless. With every year she became more posh and envelope pushing, upgrading her glam while maintaining her gender-fluid edge. Not only has Taylor captured everyone’s attention in head-to-toe Billionaire Boys Club. She’s also stole the show at the Met Gala in custom suits designed with the help of legendary costume designer Ruth E. Carter and Marc Jacobs. Sexy and steezy, nostalgic yet forward thinking, streetwear’s crowned princess is all grown up and still has it. —Ian Stonebrook
18. Travis Scott
For years, Travis Scott didn’t move the needle. He was the needle. Box braids replaced fades and consignment stores full of his merch overran malls. La Flame was so hot that Nike, Activision, and McDonald’s could appease shareholders simply by launching collabs with Cactus Jack.
The influence Travis Scott wielded at his ASTROWORLD apex is likely unparalleled. It’s also not a coincidence. Brought into the game by Kanye West, Virgil Abloh, and Easy Otabor, Scott’s’ fashion family tree is as strong as it gets. Putting hip-hop onto realtree camo, chocolate brown, and obscure vintage muddied up a genre infatuated with the runway.
To this day, Scott still stands as a forefather for the rage-meets-hype space that his successors have swarmed. He’s brought his hybrid of rock star edge and streetwear crate-digging to sporting arenas and fashion houses. —Ian Stonebrook
17. Lil Kim
When it comes to the blueprint for women in hip-hop, it’s hard to overstate the impact of Lil’ Kim. She brought high-end fashion to around-the-way Brooklyn through designers like Chanel, Versace, and Louis Vuitton. Each look was infused with personality through her colorful wigs, sometimes emblazoned with logos from Chanel and Versace. She became a muse for designers like Marc Jacobs and Donatella Versace, bringing an unapologetic sexuality that revolutionized hip-hop fashion.
From Timbs to mink coats to designer gowns, Lil’ Kim set the tone for future generations , who would emulate her raw, sexy style.She created a bold and unapologetic image that forever changed hip-hop. —Breeana Walker
16. G-Dragon
Yes, we know K-pop idols dress well. These days, it feels like every major fashion house has a K-pop star as its global ambassador. But those who’ve been around since the early days know that G-Dragon set the standard.
Debuting in 2006 as part of BigBang, a boy band formed by YG Entertainment that paved the way for the contemporary K-pop boom, G-Dragon’s rise came well before the genre’s global explosion. At a time when Western luxury brands hadn’t yet realized the power of K-pop, BigBang was dominating charts across Asia, with a cultural impact in Korea comparable to One Direction’s in the West. G-Dragon’s style immediately stood out. He performed in Alexander McQueen skull scarves and Comme des Garçons tees, effortlessly introducing high fashion and streetwear to a new demographic. He was consistently ahead of the curve. Before the Nike Air More Uptempo experienced a revival stateside in the 2010s, he was getting snapped in OG pairs of the iconic ’90s basketball silhouette.
By 2016, G-Dragon became the first Asian global ambassador for Chanel, a title he still holds today. He’s also collaborated with brands like Nike and Jacob the Jeweler on custom pieces that reflect his distinctive vision and impact. Nearly two decades into his career, G-Dragon continues to redefine what style is in K-pop, push boundaries, and inspire a whole genre to treat fashion as a form of self-expression. —Shinnie Park
15. 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
14. Shai Gilgeous-Alexander
The NBA is the flyest it’s ever been, thanks to a new generation of hoopers treating the pre-game tunnel like the runway. One player has risen above the rest: Shai Gilgeous-Alexander. The 2025 Finals MVP and Complex’s pick for Best Dressed NBA Player of 2025 has defined this era of NBA style the way Allen Iverson or Russell Westbrook did before him. Over the past few years, his tunnel fits have garnered as much attention as his game, making him a certified style icon on and off the court. From the rarest Chrome Hearts pieces to unreleased Vava jackets, SGA has become known for always making a statement with his looks and never repeating an outfit (unless it’s just a quick grocery run).
Unlike most stars, he doesn’t rely on a stylist, but instead relies on pure taste. He often spends his time during away games thrifting and building looks. Beyond that, his Converse Shai 001 is the rare basketball shoe that’s transcended into the lifestyle space. Whether you love him for his game, his style, or his elite Instagram captions, SGA embodies the league 25 years into the century. —Breeana Walker
13. 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
12. 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
11. Erykah Badu
Erykah Badu has always stood out. She entered the music scene in 1996 with her signature headwraps that matched each look, bold and big jewelry like her ankh ring, and custom pieces from Black designers with a bohemian tilt. Think languid knit dresses or intricate crochet pieces. Her love for ’70s soul and funk came through in her outfits, but it never felt like a costume.
As her career progressed, she was introduced to luxury fashion designers like Tom Ford, who featured Badu in a fragrance campaign in 2008, Riccardo Tisci, and Thom Browne. These relationships have manifested through her impressive history of custom Met Gala looks. You see someone who is clear about what they like and who they are, whether wearing patchwork suit with a long cape from Marni in 2022, or an abstract floral dress from Comme des Garcons in 2024. Sometimes her looks steered into avante garde territory, like a sculptural Rick Owens ensemble or a full head piece incorporating a range of colorful jewels.
Whatever her vibe, she makes everything she touches her own. Last year, the CFDA recognized this when they granted her with the fashion icon award. Badu never needed their validation, but for documentation as one of the most individual, best dressed women in music, the honor is well deserved. —Aria Hughes
10. 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
9. 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
8. David Beckham
Futbol fashion has been fronted on by American men of a certain ilk for quite some time. David Beckham transcended all of that by becoming an international icon whose wardrobe knew no barriers. Meeting Nelson Mandela with cornrows? He did that. Marrying Posh Spice in a purple tux straight from Paisley Park? Yessir. Dapping Prince Charles in a durag? Check again.
Beckham possessed the rare ability to dress like rules didn’t apply to him, without ever acting as though he was trying to break them. On the pitch, he made Adidas cleats and kits of every origin look awesome. Off of it, he became a menswear muse in his later years. Aesthetically, he was the Euro Michael Jordan without ever having MJ jeans atrophy.
You’d think in 30-plus years of fame there’d be a bad Beckham fit floating around on the internet, and by most measures there are. But somehow even the Zoolander leather or low-rise denim ooze nostalgia more than give cringe, cementing the soccer star’s seriously scattered but ultimately awesome legacy of looks. —Ian Stonebrook
7. Allen Iverson
The tunnel is a premier piece of the NBA today. Superstars like Shai Gilgeous-Alexander and Russell Westbrook made themselves that much bigger with their gameday dress. None of that would have been possible without Allen Iverson. Rooted in raw authenticity, The Answer introduced hip-hop style to the NBA locker room. Baggy sweatsuits. Cornrows. Shooting sleeves. Throwback jerseys on the sideline. Crooked fitted caps at the press conference. You can spot all of the above in any basketball arena in the world to this day, and you can thank Iverson for it. When your style has a global ripple effect that lasts over two decades, it’s not hard to give it high praise. Iverson changed the game forever. —Mike DeStefano
6. 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
5. 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
4. 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
3. Rihanna
Paparazzi-crowded sidewalks, Met Gala steps, and center field at the Super Bowl are equal playing fields for Rihanna.
A 20-year career that’s impacted each continent has seen stadium-status costumes and red-carpet class. But it’s the candid nights on the town, the errand running outfits, that established Rihanna as not just a style icon but a bankable brand.
In the early 2010s, her trademark sass got sharper, stronger, and more relaxed. Gone were the pop princess tropes like sequin dresses or blazers with epaulettes. In were oversized tops that defined here “don’t give a fuck” attitude. At the same time, Rihanna was rocking opulent offerings from Guo Pei and performance garb that made Madonna look cautious. Bad Gal Ri Ri was more than a handle, it was quite literally a whole mood.
Akin to Kanye, Rihanna was able to market and monetize her edge better than peers with more Billboard plaques but less guts. Her FENTY empire has exploded in worlds of lingerie, footwear, and cosmetics and dominated department stores, while still toeing the line between risky and revered.
Baby bumps and momming have created somewhat of a full circle arc of returning to America’s sweetheart status. But don’t get it twisted, she’s still putting that shit on, pushing the envelope, and appearing generally unbothered.
Despite a decade-long drought since her last album, Rihanna is both a boss and a paragon. She doesn’t have to post, tour, or put out new music to hold public adoration and make billions through beauty. She’s the only girl in the world who can break rules and attain corporate backing at the same damn time. There’s only one Rihanna. —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