The 2026 Winter Olympics have officially kicked off in style, with Milan, Italy, hosting the opening ceremony on February 6.
While the world’s top athletes prepare to compete across snow and ice through February 22, the opening red carpet night at the iconic Teatro alla Scala drew a wave of celebrities eager to soak in the Olympic moment.
From Hollywood heavyweights to pop icons and former Olympians, here is Bored Panda’s list of the 10 worst-dressed celebrities whose fashion moments failed miserably.
#1 Stanley Tucci
The acclaimed actor, best known for films like The Devil Wears Prada, The Hunger Games, and Julie & Julia, opted for a muted look at the Milano Cortina 2026 opening ceremony.
He stepped onto the La Scala red carpet in a navy padded jacket layered over a chunky white turtleneck, paired with slim black trousers.
He finished the look with black leather shoes, round-frame glasses, and a clean-shaven head.
Image source: Vittorio Zunino Celotto/Getty Images
#2 Marisa Tomei
The Oscar winner beloved for My Cousin Vinny and her role as Aunty May in the MCU, Tomei went in an unexpectedly subdued direction.
She opted for a long black coat-dress featuring multicolored embroidered diamond motifs.
The 61-year-old paired the look with black ankle boots, loose waves parted at the center, and a small structured clutch.
Image source: Vittorio Zunino Celotto/Getty Images
#3 Monique Coleman
Best known for Disney’s High School Musical franchise, Coleman attended the Milano Cortina 2026 Winter Olympics opening ceremony at Teatro alla Scala in Milan.
She opted for a navy zip-up tracksuit-style ensemble paired with wide-leg trousers. She accessorized with a metallic silver clutch and a chunky bracelet.
Unfortunately, her sporty footwear clashed with the formal venue, though her slicked-back hairstyle and bold red lipstick elevated the look.
Image source: Vittorio Zunino Celotto/Getty Images
#4 Adam Rippon
Rippon is a retired Olympic bronze medalist in figure skating. He is also a pop-culture favorite known for his sharp wit and TV appearances in shows like Dancing with the Stars, RuPaul’s Drag Race, and Messyness.
For the opening ceremony, he made a bold choice that leaned more toward a high-neck ugly-holiday-sweater vibe than high-fashion red carpet. The pattern on the sweater featured the Olympic rings, which he paired with tailored black trousers and chunky black loafers. His hair was neatly groomed.
Image source: Vittorio Zunino Celotto/Getty Images
#5 Devon Lee Carlson
The fashion influencer and founder of Wildflower Cases, known for her cool-girl California aesthetic, Carlson opted for an overly casual style for the Milano Cortina 2026 opening ceremony.
She wore a red-and-cream varsity-style cardigan layered over a black turtleneck and relaxed black trousers. She complemented her outfit with black ankle boots and a small structured handbag.
The 31-year-old kept her accessories minimal, wearing her hair loose and makeup natural.
Image source: Vittorio Zunino Celotto/Getty Images
#6 Gracie Gold
The Olympic bronze medalist, a six-time Grand Prix medalist, and a two-time U.S. national champion, Gold went full glam for the Winter Olympics 2026 opening ceremony.
She wore a dramatic blush-pink feathered jacket paired with a heavily sequined ombré skirt that faded from soft pink to deep red and black.
The combination of feathers and heavy sequins created a distracting silhouette that competed with her classic red lipstick and a neat updo.
Image source: Vittorio Zunino Celotto/Getty Images
#7 Usher
The Grammy-winning R&B icon behind hits like Yeah! And Confessions, Usher brought a rugged, off-duty energy to the red carpet.
He stepped out in a jumbo Ralph Lauren fur-lined bomber jacket marked with the Olympic and Team USA logos. He paired it with a partially unbuttoned denim shirt, faded blue jeans, and brown suede boots.
Usher complemented his outfit with a black Olympic-branded scarf, aviator sunglasses, and a chunky belt buckle.
Image source: Vittorio Zunino Celotto/Getty Images
#8 Michelle Yeoh
The Oscar-winning star of Everything Everywhere All at Once and Crouching Tiger, Yeoh opted for an understated, almost minimalist look at the Milano Cortina opening ceremony.
She arrived in an all-black ensemble featuring a long-structured coat layered over a sleek top and tailored trousers. Yeoh finished her look with a wide-brim black hat, white platform sneakers, and loose, straight hair tucked under the hat.
Image source: Vittorio Zunino Celotto/Getty Images
#9 Benito Skinner
Best known for Over Compensating and sharp pop-culture satire, Skinner brought an oddly casual energy to the red carpet.
He layered a bright red color-blocked puffer jacket over a USA-themed Olympic knit, pairing it with relaxed cream jogger-style trousers.
Skinner elevated his look with black lace-up boots, scrunched socks, and neatly styled hair.
Image source: Vittorio Zunino Celotto/Getty Images
#10 Donatella Versace
The legendary creative force behind the Versace empire, Donatella, leaned into her signature aesthetic.
She wore a body-hugging red midi dress with ruched detailing at the neckline. The 70-year-old styled the look with sheer black tights and towering black platform heels.
Donatella’s platinum-blonde hair was worn sleek and center-parted, paired with heavy eye makeup and nude lips. For accessories, she carried a small black handbag.
Image source: Vittorio Zunino Celotto/Getty Images
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