By Jessica Wedemeyer
2:41pm PDT, May 15, 2025
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Take a look back at the best and worst celeb style moments of May 2025 so far, starting with this bold getup…
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.
Keep reading for more of the month's biggest celeb style hits and misses…MORE:
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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!
