34 Of The Most Daring Looks Celebrities Unveiled In 2021

Lockdowns the world over have seen many of us glued to the sofa in our old and scruffy sweatpants. But celebrities? They’ve still pulled out all the stops to dazzle us with their daring style. From awards to premieres, to — of course — the Met Gala, let’s take a peek at 34 of the boldest and bravest looks from showbiz this year.

34. Serena Williams, Met Gala

Tennis legend Serena Williams swept into the Met Gala in a mesmerising cape of pink feathers. The ombré shawl travelled right down to the ground, enveloping Williams in a flow of pink shade. And underneath? A silver-laced bodysuit designed by Gucci and decorated with pink glittery stars, of course! “[Williams] served a royal look tonight,” her husband, and Reddit co-founder, Alexis Ohanian posted proudly on Instagram. Certainly it was an outfit befitting the 23-times-Grand-Slam-winning “Queen of Tennis”! 

33. Kate Middleton, No Time to Die premiere

Wow! In an outfit fit for a duchess, Kate Middleton quite literally dazzled crowds at the London premiere of No Time to Die. For the glamorous event, the royal slipped into a golden gown dreamed up by one of her favourite designers — Jenny Packham — complete with a floor-length cape. The ensemble was completed by sequins and beads, and golden O’nitaa earrings just made the overall look even more shimmery. People magazine reported that Daniel Craig told Kate, “You look jolly lovely.” She’s a real-life golden Bond girl! 

32. Kim Kardashian, Met Gala

Kim Kardashian arrived at the Met Gala in a look that immediately became a meme and we can see why! Head-to-toe in black, Kim’s floor-length ponytail was the only part of her that was exposed. The black-out look, designed by Balenciaga, was made up of a bodysuit underneath a T-shirt dress, matched with a balaclava and gloves. But in true Kim K style, the star was complete with a face full of makeup hidden beneath, as revealed on Instagram by her makeup artist Mario Dedivanovic. Confused? Well, “American Independence” was the theme of the event, and, as Kim herself remarked, “What’s more American than a T-shirt head to toe?”

31. Lil Nas X, Met Gala

Three bold looks over the course of the year is pretty impressive. But three in one night? Lil Nas X is certainly dedicated to the cause! For his first Met Gala, the Old Town Road singer arrived at the Metropolitan Museum of Art in a golden cape – and flowing train – fit for new music royalty. Next, he revealed a golden suit of armour that was shiny enough to see your reflection in. Nas finished the look in a sparkling – you’ve guessed it – golden Versace bodysuit! 

30. Harry Styles, GRAMMY Awards

Harry Styles had a duty to impress on the red carpet of the Grammy Awards. He started the event with a performance of his cheeky hit single, Watermelon Sugar, after all. He was also up for a few awards, and in true superstar fashion he wore three different outfits, all featuring feather boas! He kicked off proceedings in a look we like to call ‘Granddad-chic’: a clashing plaid blazer and sweater, brown bell-bottoms and a purple boa. How does he pull it off?

29. Billie Eilish, Met Gala

As co-chair of the event, Billie Eilish mesmerised fans at the Met Gala in a pale-pink Ocar de la Renta ball gown. Wanna know what made this look even more bold? It’s totally different to the singer’s usual baggy clothes and dark hair. The creative director of Oscar de la Renta, Fernando Garcia, revealed to The New York Times that Eilish wanted to surprise everybody with “a look she hasn’t done before.” With a massive 15-foot train and glittering Cartier jewellery, she looked every inch the girly-girl. In fact, Vogue magazine claimed that the gown was influenced by Marilyn Monroe’s 1951 Oscars outfit. 

28. Dan Levy, Met Gala

Dan Levy, star of Schitts Creek, wore an intricate look of which his on-screen persona, David Rose, would be proud. For his first Met Gala, the actor wore a Jonathon Anderson creation with statement puffy sleeves and a map design. If that wasn’t interesting enough, the design is actually an adaptation of artist and LGBTQIA+ activist David Wojnarowicz’s work. Levy told Vanity Fair magazine he wanted to reflect Wojnarowicz’s celebration of “queer love and queer visibility,” while also sending a reminder that “there’s a lot more that needs to be done.” He continued, “I think that has always kind of been what the Met has embodied... It’s not just clothes, you’re celebrating the impact that fashion can have.”

27. Halle Berry, Oscars

Movie legend Halle Berry was called into action as an award-presenter at this year’s Oscars. For the occasion, the “Best Actress” winner wore a strapless mauve dress designed by Dolce & Gabbana, with flowing fabric and a bow at her midsection. But what really caught the attention was her bold new hairstyle. Moments before appearing on the red carpet, Berry teased the chop on her Instagram account, showing a pile of hair on the floor. She didn’t disappoint, later revealing an angled bob with short bangs. Berry told online paper Huffington Post, "I am my best self when I have super-short hair.” Well, short hair certainly brought the actress luck for her 2002 Oscar win!

26. Timothée Chalamet, Met Gala

For what has been referred to as “fashion’s biggest night out,” Timothée Chalamet broke all the rules. As co-chair of this year’s event, we guess he’s kind of allowed. The actor wore white sweatpants tucked into socks, and white classic Chuck Taylor Converses. Well, the actor actually walked a whole ten blocks to the event, which he recorded on an Instagram livestream for his millions of followers, so we suppose he had to keep comfy! Attendees of the event usually choose one designer to wear, but Chalamet continued to break the rules. He told Keke Palmer, host of the event, that his look included a “mix of everything!”

25. Jake Gyllenhaal, Tony Awards

Jake Gyllenhaal was tickled pink on the red carpet for the Tony Awards. The actor cut a bold figure in all rose, including a — you’ve guessed it — pink satin cummerbund. He might have missed out on the award for which he was nominated, but he’s a fashion winner in our eyes!

24. Billie Eilish, No Time To Die premiere

Eilish looked every inch the chic Bond villain in this rather adrongynous ensemble. The singer-songwriter wore a black sparkly jacket over a shirt of the same print, paired with baggy trousers and chunky Gucci heels. Eilish was sort of a guest of honor at the event, as she wrote and sang “No Time to Die”, the title track of the most recent Bond release.

23. Jennifer Lopez, Joe Biden’s inauguration

Jennifer Lopez looked a vision earlier this year at Joe Biden’s inauguration. True, Kamala Harris and Jill Boden both donned bright colours, but J-Lo still stood out in her dazzling white outfit. Well, her choice was no accident. The pure tone paid homage to the suffragettes, as it was one of three significant colors they used to signify their battle to win the right to vote for women. The matching tweed jacket, blouse and trousers complete with sequins were all designed by Chanel and only added to the spectacle of her performance of “America the Beautiful”.

22. Kaley Cuoco, Emmy Awards

Kaley Cuoco dazzled fans in her neon-yellow dress at the Emmy Awards. The gown, custom made by Vera Wang, included a daring split up her thigh and was paired with matching strappy heels. The outfit also had flowers adorned onto the straps, which only served to make the look even more bold. We think this was a great choice of outfit for the actress’s first red-carpet appearance since her split from husband Karl Cook. 

21. Nick Jonas, Billboard Music Awards

We’re green with envy at Nick Jonas’s bravery in wearing such a cool outfit! The singer wore a baggy green jacket, trousers, and silk blouse to host the awards. His appearance was even more special bearing in mind he’d suffered a bike injury just a few days before. The singer tweeted: “I started this last week by taking a brutal tumble on a bike fracturing my rib and ended it hosting the @bbmas with my incredible wife by my side who helped me every step of the way to recover and feel my best”.

20. Meghan Markle, school visit

Red alert! In a far cry from the muted colours and demure outfits she wore as a royal, Meghan Markle wore this ensemble to read her book, The Bench, to a group of second-grade pupils at an elementary school in New York. From the heels to the jacket, she looks very chic in this raspberry outfit, which is perfect for fall.

19. Maisie Williams, Met Gala

Is that really you, Maisie Williams? The actress totally transformed her appearance for the Met Gala this year. We’re getting serious goth vibes from the leotard dress, mesh sleeves and tights, and black crystals. For this look, Williams transformed her blonde locks to match the all-black outfit. The Game of Thrones actress told TV’s E! News that the outfit was designed by her beau, Reuben Selby, and inspired by The Matrix.

18. Haim, Grammy Awards

Seeing triple! Sister power trio Haim looked quite the girl group in their matching blue outfits. Este, Danielle and Alana Haim all wore custom Prada ensembles, but each with their own individual twist — one with cut outs, one with pants and one with a turtleneck.

17. Anya Taylor-Joy, Emmy awards

As Coldplay would doubtless have observed, it was all yellow! Mirroring her entrance into the world of acting, Anya Taylor-Joy took the Emmys by storm. Her sunshine-toned dress, designed by Christina Dior, was a paler shade than the billowing bright-yellow shawl that trailed behind her in a dramatic train. The look is certainly fit for a darling of the screen!

16. Lady Gaga, Joe Biden’s inauguration

Wow! Lady Gaga is used to bold looks — remember that meat dress? But for Joe Biden’s inauguration, the singer remained true to her roots while retaining an element of class. To sing “The Star Spangled Banner”, Gaga wore a custom-made Schiaparelli design, featuring a navy-blue jacket with a golden bird, which then gave way to a bright-red billowing dress. Her hair was braided with a black ribbon and her lips were a dramatic red. And to make the look still more outré? The dress was actually bulletproof! The singer told Vogue, “That has to be one of the proudest days of my whole life”. Well, she has the outfit to match!

15. Dan Levy, Golden Globes

Dany Levy made fashion history at the virtual 2021 Golden Globes. According to GQ, his eye-catching, sequin-covered outfit marked the first time Valentino had ever created haute couture for men. The magazine declared at the time that Levy’s look “was a lesson in how to upstage even the coveted Golden Globe awards themselves.”

14. Taylor Swift, Grammy Awards

Taylor Swift looked a pretty petal at this year’s Grammy awards. To pick up her award for Album of the Year for Folklore, Swift wore a suitably dreamy ensemble. The nude mesh dress was adorned with a garden of flowers and actually featured 3D embroidery to make the blooms really stand out. The singer completed the ensemble with some delicate pink heels that ensured all eyes remained on the springtime look.

13. Phoebe Waller-Bridge, No Time To Die premiere

True to form, Phoebe Waller-Bridge startled with an androgynous look for the No Time to Die premiere. The actress wore an Azzaro Couture black sparkly jumpsuit which plunged down to her midriff. The eye-catching outfit certainly flattered the co-writer of the latest Bond installment. And an equally sparkly white jacket elegantly draped over the shoulders finished off the ensemble perfectly. 

12. Micaela Coel, Emmy Awards

Micaela Coel stunned onlookers at this year’s Emmy Awards. She donned a bright-yellow outfit designed by Christopher John Rogers, which contrasted beautifully against the red carpet. The two-piece included a strapless top, which had a train detail, and a floor-length skirt. Coel was up for nine nominations for the series she wrote and starred in, I May Destroy You. And she became the only black woman to date to win in the “Outstanding Writing for a Limited or Anthology Series or Movie” category.

11. Jackson Lee, Golden Globes

Jackson – Spike Lee’s son – joined his sister Satchel to serve as the Ambassadors for the 2021 Golden Globes. And he also dressed to impress, of course – wearing a bright and stylish ensemble quite unlike the standard for men on the red carpet. He had on an almost all-Gucci outfit, but the shoes were Jordans and the sunglasses were actually by Magic Johnson’s daughter Elisa.

10. Billie Eilish, Grammy Awards

As should be clear by now, Eilish is no stranger to bold outfits, and her choice for the Grammy Awards did not disappoint. Eilish wore a Jacquard shirt, trousers, bucket hat — and even a mask — which all had the same floral print. And to top it all off, the singer actually matched her manicured nails to the print on her outfit!

9. Sarah Jessica Parker, And Just Like That… set

Sarah Jessica Parker’s alter-ego, Carrie Bradshaw, is fashion royalty. And Parker did not disappoint fans on the set of the follow-up TV drama series, And Just Like That... Known for her clashing styles, the fictional character wore a striped jumper over the top of a billowing white tiered gown. We can’t wait to see what other fashion surprises the show has in store!

8. Catherine O’Hara, Emmy Awards

Catherine O’Hara cut a bold figure in the one-shouldered outfit she wore to the Emmy Awards. The Schitt's Creek actress turned up in all-red attire of which we think her on-screen alter ego, Moira, would have beed proud.

7. Kim Petras, Met Gala

Um? Kim Petras turned up in a bizarre outfit to this year’s Met Gala. Her outfit included a 3D horse head bustier and a voluminous skirt with roses and apples. And her mane? It was suitably tied into a long braided ponytail that was probably longer than what hangs from a real horse’s rear end. Designer Taymour told Vogue, “I just wanted to work with a chill, easy-going person, and that’s exactly who Kim is”. We’d never know from her outfit!

6. Cardi B, shopping

Where to begin? We’re not quite sure what’s going on with this look. This outfit is sheer, but also has a red-toned body painted on to the fabric. The overall effect is confusing, but certainly eye-catching!

5. Beanie Feldstein, Tony Awards

Beanie Feldstein turned heads in her lime-toned outfit at the Tony Awards. The actress wore a dress by Christian Siriano that had a billowing collar. She continued the bold look all over, matching the dress to her green skyscraper heels.

4. Noah Cyrus, Grammy Awards

Noah Cyrus wowed fans at the Grammy Awards in a massive white dress that seemed to swallow the singer whole. Cyrus was nominated for Best New Artist, and chose the dress, designed by Schiaparelli, for the occasion. InStyle magazine spoke to Cyrus’s stylist, Brett Nelson, before the event, and he said, “The Cyrus family is legendary in the music industry... so I wanted something that felt very original and iconic for her. I wanted to do something that felt a little bit more art-based. She’s a cool little art kid, so I want to show that.” Mission accomplished, we think!

3. Iman Khan, Met Gala

Iman Khan looked heavenly in her outfit for the Met Gala. The golden girl wowed in a one-of-a-kind Harris Reed design. The bustier and trousers were worn underneath a caged overskirt which had golden feathers and matched her massive headpiece. The effect looks positively otherworldly! The supermodel tweeted "@harris_reed If you ever wondered what a dream coming true looks like… this is it!”

2. Cynthia Erivo, Golden Globes

Cynthia Erivo wore a spectacular neon green number to the 2021 Globes. Her stylist Jason Bolden raved about it to E! News, saying, “[Erivo] knew nothing about this dress, but she trusts me and allows me to be creative. The shoes are like skyscrapers; the color and the shape is so bold – and why not?! – to add some much-needed fantasy. The neon green tea-length dress reminds me of scuba fabric.” It shouldn’t have worked, but it did.

1. Meghan Markle, Global Citizen Live Concert

Meghan debuted a whole new look at the Global Citizen Live concert in September 2021. She was back in a short white dress, similar to the ones she’d worn before becoming a duchess, but this one was perhaps a little more sophisticated. Meghan’s style has definitely become less formal now that she’s stepped down as a senior royal, and this look epitomizes this shift.