Best Dressed Artists Of 2023

The rollercoaster ride of 2023 is quickly coming to an end, and there’s plenty to reflect back on. At HNHH, we’ve gone over the best songs and albums that the year has had to offer, as well as some of the biggest rap beefs and most memorable pop culture moments. Now, for the third year in a row, we’re looking back on a few of our favourite fashion moments within the industry from couples and singles alike. With so much negativity and drama circulating in the news, especially in recent months, there’s never been a more perfect time to pretend you’re a wardrobe critic from the comfort of your Christmas pyjamas.

This year, our focus is on people who have clearly stepped into new levels of confidence, which, in turn, has helped to elevate their sense of style. From playfully hiding potential pregnancies to finding comfort in radically altered bodies, you can certainly take inspiration from 2023’s best dressed celebs. We unfortunately couldn’t include every star who’s earned the title of “Fashion Killa” on our annual round-up, but we’re curious to hear who else you would’ve added. Let us know in the comments, and check out more of our Advent Calendar content at the link below. Happy holidays!

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Couples

Halle Bailey & DDG

With The Little Mermaid‘s release slated for May, we anticipated 2023 would be a big year for Halle Bailey. The 23-year-old certainly enjoyed her moment in the spotlight during the Disney live-action remake’s world premiere, but in the months after, she seemed happy to be back in the arms of her beau, DDG. The couple’s coordinated style moments only continue to grow more impressive as their relationship blooms, however, recent months have seen them making headlines non-stop due to the pregnancy rumours plaguing them.

To this day, we’re still unsure whether Bailey is expecting her first child. If yes, her stylist undeniably deserves a raise for near-flawlessly hiding any traces of a baby bump. Knowing DDG’s typical troll-like behaviour, we wouldn’t be surprised if he and the “Angel” singer are turning the gossip into an opportunity to clown those overly invested in their personal business while capitalizing on the accompanying content views. Even if Halle isn’t pregnant, she’s still got a noticeable glow that we hope to see carry over into the new year with more glamorous style moments.

Beyonce & Jay-Z

Beyonce and Jay-Z are both superstars in their own right, but the reason they work so well as a couple is their natural understanding of when it’s time to step back and support their other half. This year was mostly the mother of three’s time to shine as she finally embarked on her RENAISSANCE World Tour. Performances initially began in Europe, where she and Hov spent their time off from work dining at luxurious restaurants, playing Uno, and snapping sweet photos together. Rather than trying to outdo Bey, her husband focuses on looking timeless and dapper in his designer duds, allowing the “Telephone” songstress to shine brightly in more eye-catching pieces.

We previously saw him in the audience, leading friends like Kris Jenner and Offset in doing the Electric Slide while waiting for his other half to stun the crowd. Besides praising Queen B’s good looks, hard work, and dedication, both parents have also been hyping up their firstborn, Blue Ivy Carter for not only joining most of her mom’s concerts but also confidently taking criticism and using it to improve at just 11 years old. They’ve had their issues in the past, but Beyonce and her man seem more in sync than ever before at this time, from their outfits to their mindsets.

Rihanna & A$AP Rocky [+ Baby RZA]

It shouldn’t come as a surprise to see these two on our list again, especially after yet another fierce maternity (and postpartum) style season from Rihanna. The Bad Gal has been busy from the moment 2023 started, first rehearsing for her legendary Super Bowl Halftime concert, then preparing for the arrival of her second son with ASAP Rocky. While she was expecting baby RZA, we became accustomed to seeing Rih flaunting her baby bump and other curves in barely-there outfits, both with and without her man by her side. When the world found out about their exciting news in February, she was already feeling comfortable showing off her body, making it even easier to boldly experiment with fashion the next time around.

For his part, Rocky continues to mesh masculine and feminine clothing, specifically making waves with his accessories of choice. Some believe that his creatively styled hair clips inspired Drake to rock a similar look, though the Canadian faced significantly more criticism for his fashion statement. Now that Riot has completed their family, and Rihanna has had time to recover from giving birth two times over, we’ve seen the happy couple outside together more frequently, sometimes even with their sons. Their most recent date night was in Las Vegas for the F1 Grand Prix, where the chemistry between ASAP and his girlfriend was so strong it had the internet spreading pregnancy rumours all over again.

Ashanti & Nelly

Anyone who’s still single this cuffing season has likely looked at Nelly and Ashanti as an example of why spinning the block may be worth it. If you were in a toxic situation, and have done nothing to grow from that, we obviously don’t suggest reconnecting with your past flames. However, if you, like our two R&B icons, have put in serious work to change and become better, there’s no reason not to send a holiday check-in. Who knows, this time next year, you may just find yourself in matching outfits, like the glitzy ones Nelly and his partner wore to the third annual Quality Control Birthday Ball.

Much like we saw with Bey and Jay, Ashanti and the “Hot in Herre” hitmaker also seem to have found a healthy balance between shining and supporting. The smile on Nelly’s face alone when he’s with the New Yorker speaks volumes as to how he feels. Elsewhere, her willingness to constantly show off their love on social media tells us how serious their feelings are. As they continue to spoil each other with lavish gifts and healing energy, we’re excited to see what other fits this duo will pull off.

Cardi B & Offset

Cardi B and Offset are far from your average duo, but the lovebirds certainly do have a knack for making everything they touch turn to gold. Earlier in 2023 they came together with McDonalds, following in the footsteps of stars like Travis Scott and Saweetie, to develop their own meal. Of course, fast food isn’t exactly classy – or something most celebrities admit to eating – but for their campaign shoot, the couple dressed to the nines and reminded us that, beneath the fame and fortune, they’re still humans who enjoy indulging too.

The former Migos member is another man who knows how to compliment his wife without stealing her shine. For the MTV Video Music Awards in particular, Set added some of the same silver hair clips on Cardi’s avant-garde gown to his hair, perfectly complimenting his “JEALOUSY” collaborator. Speaking of the pair’s newest joint single, its visual saw them pull off noteworthy looks too, with the mother of two still managing to look like a million dollars while channelling her far less financially secure roots.

Guys

Gunna

Before he was arrested along with Young Thug and other YSL co-defendants in May 2022, Gunna was no stranger to body-shaming comments. The 30-year-old has always been a fashion lover, but despite attempts to express himself through his outfits, haters always found a way to shift the conversation to the size of his body. When he returned home from jail after taking a plea deal, Wunna was noticeably smaller, though the snitching allegations still held him back from getting the praise he deserved. Regardless, the Georgia native kept his head down and focused on making a triumphant return with a Gift & a Curse.

That and the lyricist’s physical transformation gave him the confidence necessary to get back outside, and he’s been killing it, to say the least, from flexing his skills at football games to turning up at GQ‘s Men of the Year event. Some conspiracy theorists insist that Gunna was replaced by a clone because of how different he looks now, especially in the “fukumean” visual. To be fair, spending nearly a year behind bars is bound to have lasting transformative effects on a person, so we’re eager for the YSL artist to continue introducing fans to the new and improved him.

Pharrell Williams

When the untimely death of Virgil Abloh was first announced, fashion lovers couldn’t help but wonder who would replace the creative director of the Louis Vuitton Menswear division. Of course, no one can match the Off-White founder’s distinctly original spirit, but Pharrell Williams was definitely the perfect choice to take over where Abloh left off. After taking time to quietly create his debut collection, the Virginia Beach native made his runway debut back in June as many of our aforementioned best-dressed couples watched on. In his usual nature, Pharrell made sure to push boundaries with his designs, likely knowing not everyone would understand or approve, but choosing to move forward anyway.

Among the most memorable elements from this year’s show were the pixelated designs worn by Skateboard P above, which also had the internet comparing Kim Kardashian to a Minecraft character. Besides looking spiffy for his own fashion show, the “Happy” artist made sure to look fresh when supporting his contemporaries, including Nigo, as they showed off their work. What we love about Williams’ style is that he’s constantly several steps ahead of the curve, setting the tone for anyone who doesn’t want to get caught up in the trend cycle.

Usher

Usher has a lot to live up to when he headlines the 2024 Super Bowl Halftime show following Rihanna in 2023, but we’re confident the R&B crooner won’t let us down. His vocals have always spoken for themselves, but something that only adds to the Southern artist’s seemingly endless charisma is his versatile wardrobe. This year in particular, Usher had plenty of fun with his fashion choices, with one of our favourite looks coming from the Chanel S/S24 runway show, where he sat next to Jennie from BLACKPINK in a classic bouclé tweed suit from the historic brand.

For the most part, Usher spent his summer and fall heating up the stage in Las Vegas for his residency performances, which have seen plenty of handsome looks. When heading out of Sin City for festivals, the “OMG” singer made sure he was one of the most boldly dressed names on the lineup, seriously bringing the fire to The Roots Picnic back in June. Even when he’s not working, the multi-talent likes to stay looking fresh, playing around with concepts like colour blocking and accessorizing for his Instagram photo dumps.

Drake

Drake is perhaps one of the most polarizing figures in hip-hop, but as a Scorpio, this is pretty much his purpose in life. By now, he has little left to prove to both fans and critics and as he moves into his late 30s, the Certified Lover Boy seems more confident in his decisions than ever before. Like anyone else, Drake sometimes takes pointers from his contemporaries. However, there’s plenty that he’s popularized on his own as well, even if it takes the rest of the world a little longer to catch up to his vision.

During his For All The Dogs rollout, the father of one kept us laughing with his animal-related outfits. He’s since mostly retired those, but we did also love Drake’s unconventional take on a Canadian tuxedo at a recent Toronto Raptors game. While he was on tour with 21 Sav the “Way 2 Sexy” hitmaker had his yellow Chrome Hearts apron out to remind us he’s always cooking up heat, and when he heads out on the road with J. Cole in the new year, we’ll likely only have more outfits to discuss.

Gals

Keke Palmer

Keke “Keep A Bag” Palmer had one of the biggest years of her career to date in 2023, and we’re certain that if she could find a way to capture her confidence in a bottle and sell it, she would make millions. After giving birth to baby Leodis, it wasn’t long before the Chicago native returned to work as a more elevated version of herself than we’ve ever seen before. While she was stealing the show at Usher’s Las Vegas residency and shining like a star music video sets, her baby daddy Darius Jackson was at home fighting demons over his jealousy.

Of course, Palmer didn’t go out of her way to stir the pot with her ex, but stepping into motherhood gave her both a naturally enhanced body and a higher perspective on her strength as a woman. Since walking away from Leo’s dad and filing a restraining order against him in November, the 30-year-old continues to focus on herself, most recently serving looks while hosting the annual Soul Train Awards, where she also gave a stunning performance.

Chloe Bailey

We’ve already reflected on the huge year of firsts for Halle Bailey, but lest we forget everything that Chloe accomplished in 2023. The Atlanta-born vocalist shared her debut solo album In Pieces, which she followed with two rounds of touring around the country in glitzy, curve-hugging styles that prove she’s wisely taking notes from Beyonce. For the past few years, it’s been suggested that Bailey was trying too hard to achieve an overly sexualized image as an adult after spending much of her childhood in the limelight. The older she grows, the more comfortable the fashionista seems to feel tapping into her sensuality without stepping out of her integrity.

Because life currently has them moving down different paths, we saw little of the Bailey sisters together. Still, when they did manage to link up, the pair’s glamorous gowns revealed their distinct personalities. Elsewhere, she had some of the best Halloween costumes we saw this fall, and her first Carnival experience was one for the books. Even if shining her light brightly (and showing skin while she’s at it) makes others uncomfortable, Chloe refuses to be anyone but her most authentic self, which is why we love her.

Saweetie

At the end of 2022, Saweetie shared her six-track EP, THE SINGLE LIFE, which ultimately debuted to lacklustre first week sales. Rather than letting the hate that female artists too often face for low numbers make her bitter, the California native instead spent 2023 pouring into herself – particularly her wardrobe and her love life. She and fellow West Coaster YG have been boo’d up for the past few months now, and they’ve been known to beautifully coordinate their outfits, but because of her dedication to staying icy with or without her man, we felt as though Saweetie deserved a solo spot on our list.

Her Edward Scissorhands cosplay for Halloween was incredible (and a clever clap back at anyone who’s ever questioned her ultra-long nails), and in true Cancer style, she looked more ethereal than ever while celebrating her 30th trip around the Sun in the summer. Of course, looks aren’t the only thing Saweetie served up for us over the past 12 months – singles like “SHOT O’ CLOCK” and “Hey, Hickey!” featuring Baby Tate are now available on streaming, along with her YG and Tyga collaboration, “BIRTHDAY.”

Ice Spice

Few people experience a rise to fame as quickly as Ice Spice, and there are even fewer who could make it look as good as the 23-year-old. From the very start of her career, the New Yorker set herself apart from the crowd, allowing her bright red hair, fast-paced raps, and eccentric sense of style to help her carve out her own lane. Interestingly, one of the biggest sources of drama for Spice lately has been others taking notes on her style choices – specifically Latto. Though they thankfully haven’t come to blows, we have seen subliminal shots thrown between the 777 and Like..? artists on social media, proving that the latter likely doesn’t think imitation is the most sincere form of flattery.

We’re surprised Isis Gaston even found time in her busy schedule to address the discourse about her and Latto. She’s been nominated for numerous accolades at virtually every award show, spent her summer touring around the globe for festival season, and now, is opening up for Doja Cat on the Scarlet tour. With longtime icons like Nicki Minaj and Taylor Swift on her side, we’re sure that Spice will only continue to grow more confident in her role as a trendsetter and recording artist in 2024.

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