Celebrity Fashion Misfires At Winter Olympics Ceremony

The most criticized celebrity looks in Milan

The 2026 Winter Olympics are now underway, opening with a high-profile ceremony in Milan on February 6. Italy set the stage for this year’s Games with a formal launch that blended sport, culture, and celebrity presence. Competitions will run through February 22, bringing together elite athletes from around the world to compete in a full program of winter events on snow and ice.

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Before the action began, attention shifted to a glamorous opening night gathering at the legendary Teatro alla Scala. The event served as both a cultural highlight and a celebrity showcase, with actors, musicians, public figures, and former Olympic athletes attending the celebration. Cameras focused as much on fashion choices as on the Games themselves.

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As with any major red carpet, not every outfit landed well. Bold concepts, risky styling decisions, and unusual combinations resulted in several looks that drew more criticism than praise. Some outfits clashed with the venue's formal tone, while others appeared overdesigned or poorly coordinated for the occasion.

Fashion critics and viewers quickly weighed in across media and social platforms, pointing out the least successful appearances of the night. This roundup highlights ten celebrity outfits that missed the mark, turning what should have been standout style moments into widely discussed fashion missteps.

Worst Red Carpet Looks at Winter Olympics Opening Night

Worst Red Carpet Looks at Winter Olympics Opening Nightcommons.wikimedia.org
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Stanley Tucci

Stanley TucciVittorio Zunino Celotto/Getty Images
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Gracie Gold

Gracie GoldVittorio Zunino Celotto/Getty Images

Usher

UsherVittorio Zunino Celotto/Getty Images

Adam Rippon

Adam RipponVittorio Zunino Celotto/Getty Images

Michelle Yeoh

Michelle YeohVittorio Zunino Celotto/Getty Images

Marisa Tomei

Marisa TomeiVittorio Zunino Celotto/Getty Images

Devon Lee Carlson

Devon Lee CarlsonVittorio Zunino Celotto/Getty Images

Benito Skinner

Benito SkinnerVittorio Zunino Celotto/Getty Images

Monique Coleman

Monique ColemanVittorio Zunino Celotto/Getty Images

Donatella Versace

Donatella VersaceVittorio Zunino Celotto/Getty Images

Opening night showed that Olympic-level spectacle isn’t limited to the competition itself - the style and star power drew just as much attention. Medals and results will shape how these Games are remembered, but the first public moments still set the tone.

A few celebrities made risky fashion choices that missed the mark, which is normal on the red carpet. Not every outfit lands, and that unpredictability is exactly why audiences keep paying attention.

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