The Oscars — a night of stunning gowns, sparkling jewelry, and multi-million-dollar fashion. But even on Hollywood’s most glamorous evening, the red carpet has its fair share of fashion fails. While some looks make headlines for their beauty, others become unforgettable for reasons stars wish they could forget.
Ready for a roundup of the most unexpected, awkward, and downright embarrassing Oscars wardrobe mishaps? Here are the moments celebrities probably wish had stayed behind the scenes.
Venus Williams — A Live TV Surprise (2022)
The tennis legend looked flawless in her white Elie Saab gown… until live cameras caught more than intended. During Will Smith’s now-legendary speech, Venus was seen subtly adjusting her plunging neckline — a second too late. Her wardrobe slip joined the list of unexpected Oscars dramas that year.
Jenny McCarthy — Backwards Dress Moment (1997)
Jenny’s Oscars debut turned into a fashion blooper when she unknowingly wore her Valentino dress… backwards. Even Valentino himself pointed it out! Despite the mishap, Jenny still looked stunning — maybe even started a new trend before its time?
Katy Perry — The Dress That Couldn’t Hold On (2017)
Known for bold looks, Katy’s edgy Jean Paul Gaultier gown began falling apart mid-show. With its deconstructed style and shredded fabric, it blurred the line between fashion statement and wardrobe malfunction. But Katy handled it like a pro — because what’s a little fabric loss to a pop icon?
Blanca Blanco — The Slit That Stole the Show (2017)
Blanca, known for indie films, became a headline star when her high-slit gown revealed… a bit too much. Whether it was her bodysuit or an optical illusion, the red carpet cameras caught it all. “I was so embarrassed,” she admitted after the internet went wild.
Anne Hathaway — The Unfortunate Illusion (2013)
Her pale pink Prada dress was meant to be timeless. But badly placed darts on the chest created an awkward effect that got everyone talking. Anne confessed she chose the dress last-minute — a decision she probably regretted the moment the photos hit the press.
Gwyneth Paltrow — Sheer Misstep (2002)
Wearing a see-through Alexander McQueen dress with no bra might have seemed bold at the time — until hindsight kicked in. Years later, Gwyneth admitted she would’ve added a bra and toned down her makeup. Fashion lessons sometimes come with a time delay.
Mariah Carey — Diva’s Wardrobe Woes (After-Party)
At an Oscars after-party, Mariah’s strapless gown fought to stay in place… and nearly lost the battle. Throw in a daring slit flashing her shapewear, and the night became a masterclass in staying composed. Mariah, naturally, acted like nothing happened — a true diva move.
Emma Stone — The Slit with a Mind of Its Own (2015)
Emma dazzled in her beaded Elie Saab gown — until the high slit revealed a flash of nude underwear on the carpet. Was it a disaster? Not even close. Emma smiled through it like a pro, proving that grace beats any fashion mishap.
Charlize Theron — A Backless Panic Saved by a Friend (2000)
Charlize’s Vera Wang dress nearly left her completely exposed when the back decided to betray her. Enter Julianne Moore — who dashed to the rescue with a safety pin in the bathroom. Charlize later insisted the pin stay in place… even after dry cleaning. Hollywood friendship goals!
Renée Zellweger — A Rip and a Window Escape (2005)
While leaving the Oscars, someone stepped on Renée’s Carolina Herrera gown — causing a massive rip. If that wasn’t enough, she got locked out of her house while trying to change and had to climb through a window. Moral of the story: always have a spare outfit (and a key).
The Oscars are a glamorous battlefield — and not every star escapes unscathed. But if there’s one thing these mishaps teach us, it’s this: confidence, humor, and quick thinking can turn a fashion disaster into an unforgettable Hollywood moment.