Best Dressed Artists Of 2021

From the very moment it began, 2021 was out of the ordinary. As you already know, we’ve been living in unprecedented times for a while now, with the light at the end of the tunnel often feeling as though it’s within arms reach-- and many of this year’s biggest fashion moments perfectly reflect that.

While much of 2020 was spent in the house, the last 12 months have seen industry legends get back to business as usual, with music videos, concerts, red carpets, and award shows are all making a steady return. Now that the year has come to an end, we’ve curated a list of the singers and rappers who we think absolutely killed their outfits this year, and deserve to be recognized for it.

It seems that one of the biggest perks of being a celebrity is the constant rotation of designer garments you have access to – especially once you’ve made it to a certain level of stardom, as many of the people we’re acknowledging this year clearly have. Imagine wearing pieces by legendary houses like Schiaparelli, Christian Louboutin, and Jean Paul Gaultier, all in one night? Only the number one rapper on our list could achieve such a feat.

For some, fashion (particularly luxury fashion) is nothing more than a flex of material wealth, but for countless others, it’s a form of art that’s allowed them to express themselves in conjunction with their music and other creative projects. The things that they wear are more than just clothes – they’re a part of these people’s legacy, which is exactly why so much detail goes into every Instagram picture and accessory.

As far as fashion goes, it feels as though Jay-Z has really come into his own this year. He’s looking more dapper and grown than ever before – most notably at events like his Rock & Roll Hall of Fame induction ceremony, the premiere of Netflix’s The Harder They Fall, and at the wedding of Tiffany & Co. EVP, Alexandre Arnault in beautiful Venice, Italy.

Speaking of Tiffany, the “Empire State Of Mind” artist and his very stylish wife, Beyoncé, collaborated with the luxury jewelry company for a campaign in August, posing alongside a never-before-seen painting by the late creative genius, Jean-Michel Basquiat. The couple also filmed a romantic date night ad, featuring their eldest daughter, Blue Ivy, that’s earned them plenty of praise.

“Drew Barrymore” singer SZA has spoken out about her struggles with anxiety before, but from the way that she works a red carpet (especially the way she did at this year’s Billboard Music Awards), you’d never guess that she was feeling uncomfortable.

Our favorite thing about the Missouri native’s wardrobe is just how casually cool it is. You can tell that a lot of her everyday outfits are seemingly just thrown together but in the best way possible. SZA is one of those girls who has a talent for pulling off practically everything she puts on, and unlike some other famous faces who opt for wilder wardrobes, her looks have great re-wear value and can be recreated by just about anyone.

Back in February, she graced the cover of Cosmopolitan magazine, and we’ve also seen her absolutely body her looks in the “Kiss Me More” video with Doja Cat, as well as the super spicy “Fue Major” with Kali Uchis.

While Frank Ocean may not have showcased too many outfits of his own this year, he did make waves in the world of luxury fashion with the launch of his company, Homer. “My mother was into jewellery, but in a low-key Princess Diana kind of way,” he told Financial Times, while speaking on the inception of his brand during his first interview in two years.

“My godfather was into guns, but he was also into cars, and he bought luxury-lifestyle magazines, which I became obsessed with. They became a form of play for me as a child. It was the furthest thing from my actual life at the time, and I began plotting ideas and a life in that universe. I’d look at yachts and want one. But I don’t have one because I get super-seasick.”

One of the “Novacane” singer’s most iconic moments this year happened at September’s Met Gala, when he brought a little green robot baby as his date. Ocean’s look for the night consisted of a black suede, three-piece suit by Prada (who Homer recently linked up with for a limited collab), paired with a white t-shirt, a “Dreamcore” hat, and a necklace of his own design.

Coi Leray has cemented herself as a “Big Trend Setter,” making it abundantly clear that she’s not afraid to push boundaries and wear whatever makes her feel most confident, even if that means sporting a barely-there top by Jeremy Scott’s Moschino to New York Fashion Week.

One thing that really stands out about the 24-year-old’s style is her ability to seamlessly blend masculine and feminine energy, resulting in looks that are consistently both sexy and strong, on and off stage.

Over the past few months, Leray has posted up in the Gucci store, flexed some new pieces from both the highly coveted UGG x TELFAR collab and Kim Kardashian’s SKIMS x Fendi drop, and rocked a vintage Tom Ford for Gucci sheer gown to the American Music Awards. The up-and-coming star is on an undeniable roll, and she’s showing no signs of taking her foot off our necks anytime soon.

It’s pretty safe to say that if Rihanna dresses as you for Halloween, then you’re a certified style icon. Gunna, who refers to himself as a “drip influencer,” is no stranger to the world of fashion - the man wears Margiela Tabi boots, after all - and his obvious knowledge paired with his keen skill for color coordination earned him a well-deserved spot on this year’s best-dressed list.

Wunna recently collaborated with sneaker giant Foot Locker, acting as the face of the company’s new clothing line, and didn’t hold back on flexing some of the coolest pieces from his personal collection on the ‘gram.

One of his most memorable 2021 outfits came from his guest appearance on Saturday Night Live with Young Thug. The two friends opted for bold looks (as they so often do), with the College Park-born artist confidently rocking an all-red ensemble, complete with a beret and a fuzzy coat. He also pushed the envelope at Virgil Abloh’s posthumous Louis Vuitton show, wearing a monogram caplet accessorized with the perfect amount of ice.

This past Halloween season brought us plenty of inventive ideas, with some of our favorite costumes coming from none other than “Have Mercy” singer, Chloe Bailey. The 23-year-old blew her followers away with her impressive take on Angelina Jolie’s Shark Tale character, a red-hot Betty Boop look, and last, but certainly not least, she took us inside The Matrix by paying tribute to Jada Pinkett Smith’s character from the hit franchise.

While her younger sister Halle dives into the acting industry, Chloe has been hard at work launching her solo career, which has seen countless super sexy high fashion moments that are to die for; it feels as though every other day she’s got a new fit to flex, whether it be from Rick Owens, Fendi, or Balmain.

She stunned in a delicate white Rodarte dress with a dramatic train at the Met Gala in September, strutted her stuff in an animal print gown by Nicholas Ghesquiere at Louis Vuitton while attending the Grammys in March, and showed off plenty of skin in a sheer black number from Valentino at the BET Awards.

A$AP Rocky is a man with plenty of confidence, there’s no denying that. In May, the Testing artist was seen wearing an iconic Vivienne Westwood kilt on the May cover of GQ, with the publication referring to him as “the prettiest man alive.” Other shots from the photoshoot included gorgeous pieces from Chanel, Celine Homme, Loewe, and Hermès, just to name a few.

Following the cover story, Rocky unveiled his role in a collaborative campaign with “smooth shopping” app, Klarna. The clip sees the New Yorker head to his local bodega, dressed down in a durag, housecoat, and some slippers. After being teased about his casual outfit by locals, the “Changes” rapper steps inside where he’s transformed into Pretty Flacko, wearing a fresh all-black fit complete with some shiny grills.

The 33-year-old has a seemingly effortless ability to perfectly accessorize any outfit, and not to mention the way he so often coordinates OOTDs with his girlfriend, who happens to be next up on our list.

It wouldn’t be a best-dressed list if Rihanna’s name wasn’t included somewhere. The Fenty fashionista has some of the most legendary New York street style of our generation, and she covered major publications like Vogue Italia and Dazed with incredible editorials over the past 12 months, reminding us that she really is something of a creative genius.

BadGalRiri and her beau arrived fashionably late to this year’s Met Gala, both making bold choices for the “In America: A Lexicon of Fashion” theme. The Barbadian singer has been attending the event on-and-off since 2007, and has become know n for absolutely eating up the red carpet with gorgeous designs from the minds of Stella McCartney, Guo Pei, Comme des Garçons, John Galliano, and more.

This year, Rihanna shocked everyone by wearing an oversized Balenciaga coat designed by Demna Gvasalia on the carpet, prompting some to comment that her look felt off-theme and even out of character compared to her more dramatic looks worn in the past. On the red carpet, the entrepreneur said, “I’m an immigrant and that’s my take on American fashion.” Sounds like some out of the box, icon behaviour if you ask us.

As always, Tyler, The Creator put together countless cool looks over the past few months, appearing on the cover of XXL Mag and even adding plenty of new must-cop options to his Golf Wang winter collection.

Much like his good friend A$AP Rocky, the 30-year old has leaned into embracing his feminine side, often playing around with gentle pastel colors like pink, yellow, and blue, using classic accessories like pearls to create a bold Golf x Fleur belt buckle, and creating dimension in his looks thanks to his layering skills.

The “Yonkers” rapper has an obvious eye for design in everything he does, whether that be creating merch to sell at one of his sold-out shows, putting together a look to kick it with some friends, or designing his latest collection for his ever-inspired fan base.

If anyone has delivered us consistency this year, it would have to be Doja Cat. The 26-year-old started 2021 off on a high note with her “Best Friend” music video in collaboration with Saweetie, and would later go on to work with Ariana Grande and Megan Thee Stallion on the “34 + 35 Remix” visual, both of which saw the “Ain’t Shit” singer looking grown and glam. 

While some may describe Doja’s internet persona as “unusual,” we happen to think that the Los Angeles-born starlet has a talent for authentically expressing herself through not only her music, but also her makeup and fashion, which she’s been known to beautifully coordinate and subsequently flex on the ‘gram.

Designers that she wore this year include Roberto Cavalli, Issey Miyake (who she’s said is her personal favorite), and Olivier Rousteing for Balmian. The release of her Grammy-nominated album Planet Her in the summer saw her collaborate with renowned photographer David LaChapelle for an avant-garde shoot that so perfectly captures the project’s bold, vivacious energy. As if all of that weren’t enough, she also linked up with fashion brand Pretty Little Thing for a second collection of her own.

As an Aquarius, it’s always been in Scott Mescudi’s nature to be different. Now that he’s in his late 30s, the actor/musician has shared that he’s finally come to terms with this and has learned how to effectively embrace it and love himself instead of fighting his demons through other outlets like substance abuse.

While he’s not the first man in history to rock a dress or skirt in the public eye, he is one of the few who does it consistently and always with the same level of confidence. At the CFDA Awards he paid tribute to the late Nirvana front-man Kurt Cobain with a custom bridal gown designed by ERL’s Eli Russell Linnetz, and while on Saturday Night Live back in April, he wore a gorgeous floral dress designed by his late friend and CEO of Off-White, Virgil Abloh.

“I was at this point where I was looking on my phone, kind of looking at all these different stores and looking at dresses. I was just like, this is cute, this is cute. And then I finally realized, yo, I’m gonna get Virgil to do this. I’m gonna see if he has time, ‘cause he’s crazy [busy], he’s got a lot of things he’s doing,” Kid Cudi shared in an interview following the garment’s debut. The “Pursuit of Happiness” artist also rocked a skirt and blue hair at New York Fashion Week, and didn’t hesitate to bring his A-game a few weeks later for Paris Fashion Week.

Like some of the other names on our list, Kehlani has a seemingly natural ability to intertwine their masculine and feminine sides, leaning into either, or both, flawlessly at any given time. The mother of one proved that she’s a force to be reckoned with during NYFW, donning Cruella DeVille-esque hair and dropping off looks that consisted of denim, strong, monochrome power suits, and edgy-but-preppy school girl vibes.

Following that impressive haul of outfits, the “Toxic” singer flew across the pond where she also absolutely killed it at London Fashion Week, revealing on Instagram that Erdem’s designer had “pulled one of his favorite designs out of the archive” especially for her to wear.

In September, Kehlani lost her Met Gala virginity, wearing a glimmering suit by Aliétte, made up of long, straight-leg silver pants and a cropped jacket featuring sharp, pointed shoulders that emphasize power and strength. As far as magazines go, publications like Rolling Stone, Playboy, and them were all happy to feature the R&B vocalist, only expanding her impressive, ever-growing portfolio.

When Lil Nas X dropped off “Old Town Road” in 2019, we don’t think anyone predicted that the Atlanta-born artist would take the world by storm the way that he has – especially over the past few months.

While gearing up for, and following the release of his debut project, MONTERO, the 22-year-old gave us a roster of looks that won’t soon be forgotten, including his golden, Lady Gaga-esque transformation at the Met Gala, his purple Versace gown for the MTV VMAs red carpet, as well as an iconic, baroque-style collaboration with legendary designer Jean Paul Gaultier that had his followers green with envy.

As far as magazine covers go, Nas nabbed practically all of them in 2021. He was named one of GQ’s Men of the Year, appeared in the Wall Street Journal’s Innovators Issue, showed off his chiseled abs and some other preppy looks for M Magazine, paid a gorgeous tribute to the late Jimi Hendrix with VMAN Magazine, and stunned in a monochrome moment on the cover of Entertainment Weekly. 

Few people will manage to do what Cardi B did this year (while pregnant, at that) in their lives. The 29-year-old has always had a genuine energy about her that seems to get her in all the right rooms, connecting her with people who only want to see her elevate. Most recently, she made headlines when it was announced that she’ll be joining Playboy as their first-ever Creative Director, using her inventive mind to help bring the publication to new heights alongside her.

While overseas for Paris Fashion Week, the mother of two was gifted a Birkin bag by a glamorous new friend (she already has a massive collection that she’s never been shy about showing off), also donning some legendary Schiaparelli pieces that won’t soon be forgotten. Meanwhile, her time on stage hosting the American Music Awards was equally memorable, with outfit changes from Jean Paul Gaultier, Swarovski, Christian Louboutin, Jean-Louis Sabaji, and more.

When she said “your bitch wanna party with Cardi,” on “Bartier Cardi,” the New York native wasn’t lying. Her dancehall birthday bash appeared to be a wild night, with the “Bodak Yellow” rapper showing off her sculpted figure in a revealing fit while bumping and grinding with her husband, Offset, and her take on Morticia Addams on Halloween was iconic, to say the least.