<\/p>\n
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\u2019s 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.<\/p>\n
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?<\/p>\n
These are the 25 best dressed celebs of the 21st century. list below.<\/p>\n
Timoth\u00e9e Chalamet<\/a> 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<\/a> 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.<\/p>\n 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<\/a>, donning matching JUUN.J suits with Zendaya on the Dune: Part Two press tour, wearing a custom pink Chrome Hearts<\/a> 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 New York City, Chalamet has consistently balanced playfulness with polish.<\/p>\n Since 2024, he\u2019s 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\u2019ve honed a style that\u2019s increasingly experimental yet deeply authentic to Chalamet. His looks walk a fine line between humor, high fashion, vintage, and streetwear\u2014a rare feat that captures why he\u2019s become one of the most exciting dressers of his generation. \u2014Shinnie Park<\/p>\n<\/div>\n In her nearly two decades in the public eye, Kim Kardashian<\/a> went from behind-the-scenes stylist to billionaire beauty mogul.<\/p>\n The through line is SKIMS<\/a>, 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\u2014then at the peak of his powers \u2014shifted her style from club socialite to John Galliano gowns.<\/p>\n Curves became couture and Fashion Week went full celeb. From fronting the biker shorts movement to unarchiving Marilyn Monroe\u2019s infamous \u201cJFK\u201d dress<\/a>, Kardashian\u2019s ability as a trendsetter and provocateur grew as the world watched.<\/p>\n 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. \u2014Ian Stonebrook<\/p>\n<\/div>\n When you are one of the biggest pop stars of the 21st century, you have to look the part too. As Justin Bieber\u2019s<\/a> 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\u2019s Jerry Lorenzo<\/a> and well-executed merch that riffed on Marilyn Manson concert tees and \u201990s 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\u2019s refined looks.<\/p>\n Befitting his stature in pop culture, he\u2019s caught criticism for his wardrobe. Love it or hate it, it\u2019s helped redefine the traditional pop star uniform in a way we hadn\u2019t 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\u2019t have an awkward tween phase? \u2014Mike DeStefano<\/p>\n<\/div>\n There isn\u2019t a super model more synonymous with women\u2019s fashion than Bella Hadid. Scroll through any fashion girl\u2019s Pinterest mood board and you\u2019ll almost certainly find her face \u2014 or at least one of her outfits. The model has cycled through multiple style eras, from her early \u201cLA model off-duty\u201d 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\u2019s responsible for reviving everything from Bayonetta glasses<\/a> to Adidas Sambas. Anything Hadid touches (or rather, wears) turns into gold. She\u2019s 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.<\/p>\n Hadid\u2019s style represents the cultural mood. Her ability to shift seamlessly between personal style and high fashion cements her as an era-defining icon. \u2014Shinnie Park<\/p>\n<\/div>\n 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\u2014a sincere provocateur who\u2019s managed to translate his eccentric energy into a one-of-one personal style.<\/p>\n In the early 2010s, Young Thug<\/a> embodied Atlanta swag<\/a>: 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\u2014a 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.<\/p>\n 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 \u201cbetter\u201d on this list, but it\u2019s 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. \u2014Dimas Sanfiorenzo<\/p>\n<\/div>\n 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.<\/p>\n By the mid 2000s, Capo\u2019s catalog caught up to his charisma by way of \u201cWe Fly High\u2019\u201d and Complex covers. He became a boss in his own right, departing Dipset and spreading his wings with ByrdGang. In that time \u201cChrome Jones\u201d was born, trading in oversized throwbacks for fitted henleys and heavy metal accessories. New York and New Orleans both took note.<\/p>\n 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 \u201crevived\u201d Pelle Pelle<\/a>. Quiet as kept, Jones\u2019 instincts have aged better than some of his more popular peers.<\/p>\n An instigator on wax, an incendiary when poppin\u2019 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\u2019t setting the trends he\u2019s bending them in his favor. That\u2019s muscle. \u2014Ian Stonebrook<\/p>\n<\/div>\n Teyana Taylor\u2019s 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\u2019t while emotion and authenticity endeared her to communities couture, contemporary, and queer.<\/p>\n 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<\/a> or Ye\u2019s lack of direction denied her musical support<\/a>, it all gained her attention and even a hive.<\/p>\n 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\u2019s attention in head-to-toe Billionaire Boys Club. She\u2019s also stole the show at the Met Gala<\/a> 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\u2019s crowned princess is all grown up and still has it. \u2014Ian Stonebrook<\/p>\n<\/div>\n For years, Travis Scott<\/a> didn\u2019t 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\u2019s could appease shareholders simply by launching collabs with Cactus Jack<\/a>.<\/p>\n The influence Travis Scott wielded at his ASTROWORLD apex is likely unparalleled. It\u2019s also not a coincidence. Brought into the game by Kanye West, Virgil Abloh, and Easy Otabor, Scott\u2019s\u2019 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.<\/p>\n To this day, Scott still stands as a forefather for the rage-meets-hype space that his successors have swarmed. He\u2019s brought his hybrid of rock star edge and streetwear crate-digging to sporting arenas and fashion houses. \u2014Ian Stonebrook<\/p>\n<\/div>\n When it comes to the blueprint for women in hip-hop, it\u2019s hard to overstate the impact of Lil\u2019 Kim. She brought high-end fashion to around-the-way Brooklyn through designers like Chanel<\/a>, 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.<\/p>\n From Timbs to mink coats to designer gowns, Lil\u2019 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. \u2014Breeana Walker<\/p>\n<\/div>\n 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\u2019ve been around since the early days know that G-Dragon set the standard.<\/p>\n 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\u2019s rise came well before the genre\u2019s global explosion. At a time when Western luxury brands hadn\u2019t yet realized the power of K-pop, BigBang was dominating charts across Asia, with a cultural impact in Korea comparable to One Direction\u2019s in the West. G-Dragon\u2019s style immediately stood out. He performed in Alexander McQueen skull scarves and Comme des Gar\u00e7ons 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 \u201990s basketball silhouette.<\/p>\n By 2016, G-Dragon became the first Asian global ambassador for Chanel, a title he still holds today. He\u2019s 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. \u2014Shinnie Park<\/p>\n<\/div>\n Kid Cudi<\/a> cut his teeth folding clothes at American Apparel and selling shirts at BAPE\u2019s 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.<\/p>\n A debut mixtape with then-streetwear heavyweight 10.Deep and a record deal with Kanye West didn\u2019t change Cudi\u2014it influenced his partners. Streetwear embraced the martian and Yeezy started singing. As Cudi\u2019s 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.<\/p>\n Cudi\u2019s 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. \u2014Ian Stonebrook<\/p>\n<\/div>\n The NBA is the flyest it\u2019s 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\u2019s pick for Best Dressed NBA Player of 2025<\/a> 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\u2019s just a quick grocery run).<\/p>\n Unlike most stars, he doesn\u2019t 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\u2019s 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. \u2014Breeana Walker<\/p>\n<\/div>\n 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 \u201cbling bling\u201d and accented each staple with Tommy Hilfiger accessories or all-white Reeboks.<\/p>\n As his solo career took off, Wayne shed his Hot Boy branding and regional wardrobe. He\u2019d flirt with the throwback jersey craze up the East Coast and (allegedly) bite BAPE by way of Clipse<\/a>. His camo-clad fits have achieved immortal status. He\u2019d look good doing all of it before becoming The Best Rapper Alive in rock star garb.<\/p>\n Wayne\u2019s 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. \u2014Ian Stonebrook<\/p>\n<\/div>\n After debuting with his self-titled project in 2017, Playboi Carti burrowed into his own insular world to become one of today\u2019s hottest trendsetters. It\u2019s been a steady ascent. The same year as his debut, he modeled for Yeezy Season 5; in 2018, he <\/a>walked<\/a> in Virgil Abloh\u2019s debut show for Louis Vuitton in addition to modeling for Off-White F\/W19<\/a>. 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<\/a> Chrome Hearts jeans, Timberland boots, and classic BAPE<\/a> camo jackets, Carti is uncompromising. He\u2019ll 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<\/a>. \u2014Antonio Johri<\/p>\n<\/div>\n Erykah Badu<\/a> 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 \u201970s soul and funk came through in her outfits, but it never felt like a costume.<\/p>\n 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.<\/p>\n 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. \u2014Aria Hughes<\/p>\n<\/div>\n 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\u2019s 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 \u201cfeminine,\u201d there were dozens of teens mimicking their every move.<\/p>\n As Uzi\u2019s career progressed, fame grew, and wallet inflated, the outfits got more experimental\u2014no 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<\/a> 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\u2019re going to get with Uzi. They could pop out for their set looking like a Fifth Element extra, toting an ultra rare Birkin bag<\/a>, or they could keep it pacific in an all-white Chrome Hearts sweatsuit. As unpredictable and unorthodox as Uzi\u2019s wardrobe can be, they always pull it off. That\u2019s the true mark of any well dressed individual. \u2014Mike DeStefano<\/p>\n<\/div>\n Lil Yachty may not wear red braids and plug a closet full of Nautica like he did in 2016, but he\u2019s remained at the forefront of hip-hop\u2019s style conversation ever since his \u201cOne Night\u201d days. The best thing about Boat\u2019s style is his versatility. One day, he can be decked out in a vintage ensemble, and the next he\u2019s stepping out in full Bottega Veneta. He might follow that up with a day where he\u2019s decked out in nothing but pieces from emerging designers like NYRVA<\/a> or Filthy Project. And we can\u2019t forget about the endless collection of rare sneakers and six-figure custom jewelry that accessorizes each and every look. It\u2019s 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.<\/p>\n The scope of Yachty\u2019s outfits is so wide because of his genuine appreciation for clothes. He\u2019s 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\u2019s not hard to become a fixture in these types of conversations. \u2014Mike DeStefano<\/p>\n<\/div>\n 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.<\/p>\n Beckham possessed the rare ability to dress like rules didn\u2019t 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.<\/p>\n You\u2019d think in 30-plus years of fame there\u2019d 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\u2019s seriously scattered but ultimately awesome legacy of looks. \u2014Ian Stonebrook<\/p>\n<\/div>\n 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<\/a>. 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\u2019s not hard to give it high praise. Iverson changed the game forever. \u2014Mike DeStefano<\/p>\n<\/div>\n Growing up in close proximity to Fairfax Avenue<\/a> 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\u2019s wardrobe has done the same. Whether he was putting an entire generation onto Supreme<\/a> box logo hoodies, rocking some of the brightest T-shirts we\u2019ve ever seen from his own brand Golf Wang, or tapping into his opulent jetsetter bag with furry ushankas and cashmere knits, he\u2019s 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.<\/p>\n 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. \u2014Mike DeStefano<\/p>\n<\/div>\n Hip-hop scholars suggest that Afrika Bambaata & The Soulsonic Force\u2019s \u201cPlanet Rock\u201d 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<\/a>.<\/p>\n Since rocking a reserved-yet-intentional Braves jersey and fuzzy Kangol for his \u201cPlayer\u2019s Ball\u201d 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.<\/p>\n 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\u2019d 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\u2019t be traced. The spirit of his style appears in Tyler, the Creator, Young Thug, and Lil Yachty, still somewhat adapted for modern times.<\/p>\n 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\u2019s funkiest dreams. \u2014Ian Stonebrook<\/p>\n<\/div>\n Pharrell Williams is not just one of the best dressed musicians ever, he\u2019s calling the shots for menswear at one of the most storied luxury houses. He\u2019s the rare talent whose transition from trendsetter to big boss is inspiring and organic. At 52 years old, he\u2019s still striding on a 25-year run that reads like a storybook.<\/p>\n 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<\/a> furthered his retail reach in apparel and footwear. A nod from Marc Jacobs led to Louis Vuitton\u2019s blockbuster Millionaire shades.<\/p>\n Even in his self-proclaimed \u201cdud\u201d 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.<\/p>\n 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\u2019s timetested-yet-timeless aesthetic. It paints a clear picture of his life\u2019s work, from N.E.R.D. to LVMH. \u2014Ian Stonebrook<\/p>\n<\/div>\n Paparazzi-crowded sidewalks, Met Gala steps, and center field at the Super Bowl are equal playing fields for Rihanna.<\/p>\n A 20-year career that\u2019s impacted each continent has seen stadium-status costumes and red-carpet class. But it\u2019s the candid nights on the town, the errand running outfits, that established Rihanna as not just a style icon but a bankable brand.<\/p>\n 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 \u201cdon\u2019t give a fuck\u201d 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.<\/p>\n Akin to Kanye, Rihanna was able to market and monetize her edge<\/a> 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.<\/p>\n Baby bumps and momming have created somewhat of a full circle arc of returning to America\u2019s sweetheart status. But don\u2019t get it twisted, she\u2019s still putting that shit on, pushing the envelope, and appearing generally unbothered.<\/p>\n Despite a decade-long drought since her last album, Rihanna is both a boss and a paragon. She doesn\u2019t have to post, tour, or put out new music to hold public adoration and make billions through beauty. She\u2019s the only girl in the world who can break rules and attain corporate backing at the same damn time. There\u2019s only one Rihanna. \u2014Ian Stonebrook<\/p>\n<\/div>\n The first time the world heard ASAP Rocky<\/a> rap in 2011, he proclaimed himself \u201cthat pretty mothafucka\u201d over a dreamy Ty Beats instrumental. It\u2019d 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 \u201cstreet goth\u201d 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\u2019s cosign, Raf Simons became a deity to them.<\/p>\n As his career progressed, the music became more experimental (and less frequent), and his cutting edge fashion sense persisted. In recent years, we\u2019ve 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.<\/p>\n Whether he\u2019s rocking Harlem staples like Pelle Pelle leathers, championing his \u201cdad swag\u201d in shirts and ties from JW Anderson\u2019s Dior, turning a courtroom arrival into a runway show, or blinding onlookers with his latest ice from Alex Moss<\/a>, 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. \u2014Mike DeStefano<\/p>\n<\/div>\n Whether you come from the generation that resonates most with his pink-ass polo and fuckin\u2019 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\u2019s personal style in some way, shape, or form.<\/p>\n Like his discography, you could probably single out any one of his style eras and make the case that it\u2019s one of the best of the 21st century. He wasn\u2019t just putting on amazing outfits, even though there have been hundreds that have been burned into our memories. The \u201cRunaway\u201d 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.<\/p>\n 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. \u2014Mike DeStefano<\/p>\n<\/div>\n<\/div>\n