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Fashion Wins: The Best Celebrity Looks of May

Kylie Jenner wearing a fitted beige dress in silk fabric with deep red prints of roses and clear flat sandals.
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They say April showers bring May flowers, so it’s time for a fresh spin on celebrity style reviews for the summer ahead. This month, we’re embracing the warmth of the impending sunshine by shining some light on the best celebrity looks to hit red carpets and city streets around the globe. The beginning of May is always buzzing with excitement as the first Monday of the month kicks off fashion’s most coveted (and judged!) event — the Met Gala. As celebs face their harshest critics right off the top, they can soon breathe a sigh of relief and return to less overwhelming themes and events to show off their best threads. 

We’ll be here as the fashion world turns to seek out the best outfits and serve them to you with positive takes on what makes Hollywood so damn stylish.

Related: The best and worst dressed celebs at the 2021 Met Gala.

Cynthia Erivo poses at an event while wearing a gown with a black low cut tank top and a long baby pink skirt with ruffles.
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Cynthia Erivo, May 26, 2022

Cynthia Erivo has stunned us as usual in a flawless gown. The actress walked the carpet at The Red Sea International Film Festival and perfectly mixed shades of black and pink to create a stunning dress that demands zero accessories — and all of our attention.

You may also like: 10 unique wedding guest dresses for spring/summer 2022 under $200.

Coco Rocha poses for the camera wearing a white and yellow costume dress that has a high neck and features a gorgeous appliqué with protruding ruffles along both sides of her body.
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Coco Rocha, May 26, 2022 

Model Coco Rocha has been serving a series of breathtaking looks during this year’s Cannes Film Festival run, but this one stopped us in our tracks. The over-the-top costume gown features a gorgeous appliqué with enough protruding ruffles to make us think that Rocha could take flight in the form of an elusive butterfly at any moment.

Related: The richest supermodels in 2021, by net worth.


Shakira walks out of a hotel with two men beside her. She is wearing a black sweetheart neck gown with a high slit and black mesh gloves.
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Shakira, May 25, 2022

Singer Shakira was snapped at Hotel Martinez during the Cannes Film Festival and we couldn’t pass on adding this outfit. The black gown features a sweetheart neck and a pair of delicate mesh gloves, and it’s giving us gothic Jessica Rabbit vibes in all the right ways.

See also: Slip dresses are here to stay and this is how to get in on the action.

Léa Seydoux is wearing a black dress short with a matching blazer. She has a white collared shirt and printed silk tie under the jacket. She's also wearing black heels to match.
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Léa Seydoux, May 24, 2022

We’re willing to bet that Diane Keaton would provide her seal of approval for this modern take on the look she once made famous in the film Annie Hall. This time around, we see actress Léa Seydoux bringing classic androgyny to life again in a summer suit while attending the photocall for her upcoming film Crimes Of The Future alongside Kristen Stewart.

You may also like: 20 accomplished women share how to dress for success.

Kylie Jenner wearing a fitted beige dress in silk fabric with deep red prints of roses and clear flat sandals.
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Kylie Jenner, May 21, 2022

We witnessed some ridiculous outfits during the multi-day wedding extravaganza celebrating the union of Kravis, but thankfully, Kylie Jenner graced us with something beautiful. The silk gown hugged her in all the right places and brought a level of elegance that felt necessary among a sea of try-hards.

Related: Kylie Jenner’s style evolution.

Anne Hathaway on the red carpet at Cannes wearing a white sequin tube top and matching skirt and shawl.
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Anne Hathaway, May 19, 2022 

If anyone is going to make a sequined tube top and matching skirt look like a million bucks — it might as well be Anne Hathaway. The actress brought her elegant sense of fashion to the Cannes Film Festival, and while her hair and makeup may have been subtle, the impact of her white gown and heart of the ocean-inspired necklace gave the cameras what they wanted. 

See also: The best red carpet looks at the 2022 Grammys.


Hilary Duff poses candidly while wearing a black fitted dress with a vine and floral gold pattern.
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Hilary Duff, May 18, 2022

Hilary Duff looked perfectly sun-swept when she was captured going about her business in New York City. Her black dress featured gold vine and floral details that feel very nostalgic — especially during a time when ‘90s fashion continues to have its moment. The delicate gold earrings, handbag and strappy sandals created the perfect addition to this look. 

You may also like: These celebrity moms have the best maternity style.

Doja Cat poses at the Billboard Music Awards wearing a long, fitted black dress with a see-through mesh top accompanied by gold pasties. She is also holding a gold purse in the shape of planet Saturn.
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Doja Cat, May 15, 2022 

Let’s just say it — Doja Cat has a strange sense of fashion! But, it’s strange in a way that makes you want to place her on the top of a pedestal like a fine piece of art. The singer took home three awards at the 2022 Billboard Music Awards and showed up to receive them wearing a truly out-of-this-world black dress, complete with a gold Saturn purse.

See also: The world’s richest rappers in 2022.

Julia Fox pushes a a shopping cart while wearing a light denim jacket over a black and white triangle bikini. She has on matching light denim knee-high boots and hand bag.
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Julia Fox, May 15, 2022 

We bet you didn’t expect to see Julia Fox land on our best-dressed list in her grocery shopping attire, but honestly, how could you not? Fox is quickly becoming a fashion icon in her own right thanks to her DIY approach to dressing herself, not to mention her complete disregard for what people think — regardless of how wild her outfits become. 

Related: This simple DIY trick will instantly upgrade your denim jacket.

Millie Bobby Brown has her hands in the air with her tongue out. She's wearing a long, fitted white dress with a high side slit, high-waist belt and sheer black fabric secured over one shoulder.
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Millie Bobby Brown, May 14, 2022

Millie Bobby Brown has grown into a stunning young woman dominating red carpets with her impeccable taste for fashion in the blink of an eye. As anticipation builds for the release of Stranger Things season 4, Millie Bobby Brown walked the red carpet premiere in Brooklyn, looking incredibly joyful in a gorgeous black and white gown fit for a superstar.

You may also like: Winona Ryder’s style evolution.


Florence Welch performs on the Tonight Show stage wearing a lacy red dress with oversized sleeves.
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Florence Welch, May 11, 2022

A Florence Welch Fashion Protection Group should be in place (if it doesn’t exist already). This ethereal rock star can do absolutely no wrong when it comes to her seemingly endless array of flowy dresses — as proven here once again when she performed on The Tonight Show Starring Jimmy Fallon.

See also: Stardust shadow is the perfect makeup trend for spring — get the look.

Julianne Hough smiles for the camera in a relaxed fit bright red pant suit and medium pink cami.
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Julianne Hough, May 11, 2022

We have another lady in red to add to the list! We’re honouring Julianne Hough and her ability to make a relaxed suit look incredibly easy to wear. The colour palette pops in all the right ways, and her attention to detail with delicate makeup and accessories has us taking notes.

Related: These nail art designs will inspire your next spring manicure.

Brandy wearing a bright yellow floor-length dress with ruffles details down each side.
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Brandy, May 7, 2022

Singer Brandy is looking the opposite of mellow in this stunning shade of yellow. She debuted the sunny look at the 5th Annual Best Buddies Celebration of Mothers, and honestly, if this bright and cheery floor-length dress doesn’t get you in the mood for summer garden parties — we don’t know what will!

You may also like: What is dopamine dressing? How colourful clothes can boost your mood.

Saniyya Sidney is wearing a blue and white pattern silk blazer with matching tailored shorts and a mini white purse.
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Saniyya Sidney, May 5, 2022 

Saniyya Sidney, who played young Venus Williams in King Richard, a biographical drama about the famous tennis-playing sisters, attended Variety’s 2022 Power Of Women event in a perfectly tailored summer suit. From the stunning satin print to the tiny purse and strappy sandals — we can’t decide which part we enjoy most from this look!

See also: 10 times representation happened for Black women and why it matters.


Amanda Seyfried wearing a aqua blue fitted top with matching wide leg pants that cover her toes.
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Amanda Seyfried, May 5, 2022 

Oversized yet untailored pants are the new big trend this season, but we prefer when there’s at least a bit of consideration for walking ability. Luckily, we feel safe reporting that Amanda Seyfried enjoyed a beautiful pair of aqua blue trousers that perfectly hid her feet without forcing her to trip over her look.

Related: This is blue beauty, and these brands are doing it right.

Sarah Jessica Parker attends the Met Gala wearing a black, white and grey gilded age theme dress that sits off the shoulder. She is also wearing a black mesh fascinator and fuchsia flower detail.
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Sarah Jessica Parker, May 2, 2022

It may not be everyone’s taste, but no one should mess with miss Met Gala herself — Sarah Jessica Parker. The actress and fashion lover called out the importance of following the theme during a video with Vogue, where she reviewed her past Met Gala looks. Not one to fail the assignment, SJP impressed the crowd with her take on the Gilded Glamour theme while honouring Black designer Elizabeth Hobbs Keckley.

You may also like: This is Sarah Jessica Parker’s style evolution.

Blake Lively attends the Met Gala wearing a rose gold and baby blue strapless metallic dress with a large train covering several steps. She has long gloves to match the dress and has included a diamond and gem tiara and earrings.
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Blake Lively, May 2, 2022

Another Met Gala master among us is the undeniably stunning Blake Lively. The 2022 Met Gala co-chair stunned her husband, Ryan Reynolds, and the audience when she performed a glamorous second outfit reveal. The careful attention to detail and metallic fabric allowed her to stand out in a crowd of celebrities begging for the cameras’ attention. 

See also: The best beauty looks at the 2022 Met Gala.

Emma Stone attends the Met Gala wearing a white knee-length dress with sheer straps, side buttons and feather details around the bottom. She has on chunk white heels with twisted diamond details wrapped around her ankles.
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Emma Stone, May 2, 2022 

Actress Emma Stone brought us all the way back to La La Land with her take on the gilded era at the 2022 Met Gala. Looking like a precious ballerina, Stone joined the iconic Gala carpet in an unassuming white dress that had just the right amount of detail to showcase her version of the theme and the simplicity of dressing to impress at one of fashion’s most iconic events. 

Related: 10 style and fashion trends to watch for in 2022.


Rachel McAdams poses at a film premiere wearing a sheer, floor-length light lime green dress with beaded detail and a matching sheer cape.
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Rachel McAdams, May 2, 2022

She may have landed on our fashion fails list in the past, but Canadian actress Rachel McAdams brought her A-game this time around. She arrived at the premiere of Doctor Strange in the Multiverse Of Madness looking like an ethereal goddess in a delicate lime green frock with beaded detailing and a matching sheer cape that perfectly captured the sun.

You may also like: Making the case for the coastal grandmother aesthetic as a lifestyle.

Kim Kardashian looks at the camera while wearing a fitted shimmer silver gown. Her long dark hair is styled wet and sits below her waist.
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Kim Kardashian, April 30, 2022

She failed to honour the theme at this year’s Met Gala — but for better or worse, Kim Kardashian brought the correct level of glitz and glamour while attending the White House Correspondents’ Association Dinner. We can only hope that if this outfit lands in a museum one day, no reality star will change themselves to wear it. 

See also: The funniest memes about Kim Kardashian’s Met Gala outfit.

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