By Jessica Wedemeyer
5:32pm PDT, Jun 2, 2025
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Take a look back at the best and worst celeb style moments of May 2025, starting with this bold getup…
Jenna Ortega donned a fantastic ombré Markgong coat-dress during Netflix's Tudum event at the Kia Forum in Los Angeles on May 31, 2025. We especially loved the extra-long belt, which trailed to the ground, and the matching cuffs. If only she'd gone without her black tights!
Keep reading for more of the month's biggest celeb style hits and misses…MORE:
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Teyana Taylor knocked it out of the park at a dinner party in celebration of the new Thom Browne boutique in West Hollywood at the Chateau Marmont in Los Angeles on May 29, 2025. The singer-actress sported an ensemble featuring several of the designer's signature elements — from the pleated skirt to the striped belt and matching tie. (We especially appreciated the contrast with her mismatched socks and pointy-toe heels.) We've never seen corduroy and tweed look this chic!
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Scarlett Johansson donned a fiery strapless gown created by Saint Laurent designer Anthony Vaccarello at the New York City premiere of
The Phoenician Scheme at Jazz at Lincoln Center on May 28, 2025. While we wanted to love his look, we couldn't deny that there was just something… off. The Oscar-nominated actress added to the effect by posing with her hands awkwardly clasped in front of her, obscuring the most interesting detail: the elegant asymmetrical draping across the midsection. Bummer!
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Ana de Armas scored mixed reviews with her look at the French premiere of Ballerina at the Grand Rex theater in Paris on May 28, 2025. While we loved the bottom half of her custom Louis Vuitton gown — the excessively ruffled skirt was superb — the top half left a lot to be desired. The strapless black satin bodice with a sweetheart neckline was just plain basic.
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Halloween is still several months away, Kacey Musgraves! The country music superstar dressed in theme during the 2025 Crunchyroll Anime Awards at the Grand Prince Hotel Shin Takanawa in Tokyo on May 25, 2025. The "Rainbow" singer channeled Sailor Moon in a school girl-style long-sleeve mini and wore her hair in extra-long pigtails with space buns on top. (Serena would be proud!) She completed her look with pointy-toe Mary Jones, knee-high socks and, inexplicably, a studded black leather choker.
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Summer is practically right around the corner, but
Miley Cyrus was dressed for a cold winter day as she arrived at the
Jimmy Kimmel Live! studios in Hollywood on May 22, 2025. While we loved her Alaïa ensemble — a pleated midi-length skirt in a deep purple shade over black tights, chunky heel pumps and a furry white coat — we wish she'd chosen something a little more seasonally appropriate … and maybe ditched the tights! After all, the look is from Alaïa's Fall 2025 collection.
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We're obsessed! Cynthia Nixon went way outside of her fashion comfort zone at a photo call for the third season of And Just Like That… at Crane Club in New York City on May 21, 2025. The Sex and the City star donned a minty Richard Quinn creation with a vintage vibe — from the oversized tie at the neck to the feathered hemline — that had us completely charmed. This just might be her best look ever!
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Natalie Portman looked red-hot as she arrived for an appearance on
The Late Show With Stephen Colbert in New York City on May 21, 2025, in a darling strapless mini with an embellished hemline. The Oscar winner completed her look with matching strappy red heels.
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Eiza Gonzalez subtly dressed in theme in Ralph Lauren during the premiere of Fountain of Youth at the American Museum of Natural History in New York City on May 19, 2025. The actress delivered a chic "lady explorer" look in a monochromatic brown ensemble comprised of a distressed leather aviator jacket over a cashmere turtleneck and a chiffon maxi-skirt.
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What's better than an in-theme fit? An in-theme fit that's accessible! Jordin Sparks donned an ensemble from Fe Noel's Target collection — a palm-print kimono over a bikini top and high-waist pants, topped off with a headscarf — during the premiere of Lilo & Stitch, which is set in Hawaii, at the El Capitan Theatre in Hollywood on May 17, 2025.
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Salma Hayek turned heads at the 2025 Sports Illustrated Swimsuit Issue launch party at the Hard Rock hotel in New York City on May 15, 2025 — but not necessarily for the right reasons. No, it was the Oscar-nominated actress' sartorial selection that had eyes widening. Her black gown featured sheer sleeves, a corset-style bodice and a skirt comprised of hair-like fibers. To make matters worse, her cuffs were lined with the same wisps of fabric. It had us, ahem… totally wigging out.
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Kris Jenner had an eyebrow-raising monochromatic menswear moment in Paris on May 14, 2025. The reality star paired burgundy slacks with a comically oversized double-breasted suit jacket with structured shoulders in the same deep-berry shade. She completed her look with coordinating loafers, a matching tie and a burgundy-and-white pinstripe button-down.
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Kim Kardashian turned heads while out and about in Paris on May 14, 2025. The reality star wore a cream Conner Ives duster featuring a feathered hemline and feather-adorned shoulders over a lacy beige bralette. She completed her look with a suede Déhanche belt and a navy baseball cap — a stark comparison to the rest of her glam getup.
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WOW.
Heidi Klum had a major fashion moment during the 78th Cannes Film Festival opening ceremony in France on May 13, 2025. The supermodel looked pretty in pink in a strapless Elie Saab confection with a thigh-high slit and a massive train.
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Jenny McCarthy was right on trend at CBS Fest at Paramount Studios in Los Angeles on May 7, 2025. The Masked Singer panelist donned a darling long-sleeve polka-dot-print Saint Laurent mini with peep-toe heels and shades. The actress first donned the dress in late 2024 — months before the polka-dot trend fully took off. (See her first stab at the ensemble
here.)
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Diane Kruger brought the drama to New York City Ballet's 2025 Spring Gala in NYC on May 8, 2025. The actress donned a strapless black Jason Wu creation with a bustier top and a sheer skirt. She finished off her look — which the fashion house described as "a vision of dark romance" — with sheer opera gloves and a Dora Marra-designer butterfly masquerade mask.
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Drew Barrymore had a stellar menswear moment at CBS Fest at Paramount Studios in Los Angeles on May 7, 2025. The actress looked polished in a crisp beige suit — a perfectly tailored jacket and flared slacks — over a white-and-blue striped button-down and a thick pink tie.
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Blake Lively had a major bridal moment outside the Late Show with Seth Meyers studios in in New York City on May 1, 2025. The actress was a vision in white in a midi-length Christopher John Rogers dress with a plunging neckline, a corseted bodice and a skirt comprised of layer upon layer of ruffled fabric.
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It was a "pajamas on the red carpet" kinda night for
Heidi Klum at The King's Trust 4th Annual Global Gala at Cipriani South Street in New York City on May 1, 2025. The supermodel donned a disappointing, figure-devouring Vetements ensemble comprised of loose-fitting slacks and a matching tuxedo-inspired jacket in the same satiny fabric.
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Kerry Washington donned Prada separates at a special screening of
Shadow Force at the AMC Lincoln Square theater in New York City on May 1, 2025. While we loved the body-skimming cut of her gold set, we couldn't help but wish she'd gone with a brighter color.
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Dascha Polanco played with proportions at PaleyLive's Walking and Talking: An Evening with The Walking Dead: Dead City at The Paley Museum in New York City on April 30, 2025. The Orange Is the New Black alum paired an oversized white blazer with a pleated miniskirt. She went sans shirt and completed her look with white pumps and white sequin-encrusted fishnet stockings.
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The jury is still out on this one… Maria Bakalova chose a unique Fendi LBD for the premiere of her film Electra at the Fine Arts Theatre in Beverly Hills on May 2, 2025. The three-quarter-sleeve midi-length dress featured a high neckline, a peplum waist, contrasting fabrics and a fit-and-flare hemline. At least it wasn't boring!
