35+ Worst Red Carpet Outfits That Made Everyone Cringe
When famous celebrities walk the red carpet, millions of people around the world watch closely. Everyone wants to see what stylish or bold outfits they will wear. But sometimes, stars don’t impress—they make big fashion mistakes that become unforgettable.
Over the years, we’ve seen some major red carpet disasters. Who can forget Bjork’s swan dress, or Whoopi Goldberg’s Dracula costume? These outfits are often listed among the worst celebrity outfits of all time.
If you love fashion, or just want to see what not to wear, here are some of the biggest celebrity fashion fails in red carpet history.
Jennifer Hudson
Jennifer Hudson wore a beautiful Oscar de la Renta dress, but the silver cropped jacket on top was a total miss. It looked more like The Tin Man’s wife than an Oscar winner. That one piece ruined the entire outfit.
Kristen Wiig
Kristen Wiig is known for her comedy, but her outfit looked more like a true crime drama than a Hollywood event. Her red dress and matching gloves made her look stiff and uncomfortable.
Faith Hill
At the 74th Academy Awards, Faith Hill wore a colorful dress that looked like a cake explosion. With too many colors and details, the dress was just too much to handle.
Cameron Diaz
Cameron Diaz wore an Emmanuel Ungaro gown that was already questionable, but the odd purple belt and messy hair made it worse. She said she wanted to look casual—but it looked more like she just woke up.
Helena Bonham Carter
Helena channeled her Harry Potter character a bit too much. Her layered black and white dress looked more like a costume than a gown. People thought Bellatrix Lestrange had shown up at the Oscars.
Kim Basinger
Kim Basinger designed her own gown—and maybe she shouldn’t have. The dress looked like a torn wedding gown with a corset and a missing shoulder. Definitely not red carpet ready.
Uma Thurman
Uma Thurman is stunning, but her dress at the Oscars was not. It had odd blue and gold fabric that looked like pieces of a medieval vest. The outfit was confusing and disappointing.
Kate Mara
Kate Mara usually looks great, but this gown with a droopy sleeve and poor fit just didn’t work. It gave off a tired and sad look, far from the glam we expect on the red carpet.
Sophia Loren
Sophia Loren wore a gown that looked like a fairy-tale costume. It may have worked at a kid’s party, but not at the Oscars. This dress belonged at Disneyland, not Hollywood.
Diane Keaton
Diane Keaton’s Ralph Lauren suit shocked everyone. People thought she was channeling her old Annie Hall character, but the look didn’t suit the glamorous night at all.
Nicki Minaj
Nicki Minaj is known for her bold style, but this outfit went way too far. Covered head-to-toe in leopard print Givenchy Haute Couture, it looked like she fell into a jungle and never came out. Even for Nicki, this was a bit much.
Britney Spears
Back in the early 2000s, Britney Spears was the teen style queen. But this tie-dye orange outfit with a top hat and fishnets was a serious fashion fail. It’s fun to look back, but this outfit definitely belongs in a fashion time capsule.
Madonna
Madonna wore a Francesco Scognamiglio fur vest, fishnets, and… forgot the pants? That’s the only way to explain her strange look at the Vanity Fair Oscar party. The Queen of Pop had plenty of bold moments, but this one had fans shocked.
Gaby Espino
Gaby Espino hosted the 26th Billboard Latin Music Awards in style—well, almost. One of her outfit changes included a super low-cut, sparkly gown where her undergarments were clearly visible. Viewers were left wondering if that was planned or a major red carpet mistake.
Anne Hathaway
Anne Hathaway looked lovely as always, but her Oscar gown featured not one, but two giant bows—one in the front, and a surprise one in the back. The design was just too much and distracted from her usual elegance.
Tyra Banks
Tyra Banks is a fashion industry icon, but her 2000 Academy Awards gown was more costume party than Hollywood glamour. The fluffy purple dress made her look like a sugar plum fairy, not a top model. This one was not her best red carpet moment.
Kim Kardashian
Today, Kim Kardashian is a true style icon with a wardrobe full of designer couture. But back in the early days, it was all about sweater dresses and huge waist belts. One particular look even featured guitar designs—definitely not her best fashion moment.
Salma Hayek
Salma Hayek is naturally stunning, but this over-the-top dress with heavy chain embellishments did nothing to help. The odd color and flashy design turned a glamorous star into a fashion fail on the red carpet.
Celine Dion
We love Celine Dion’s bold fashion risks, but this time it didn’t work. Wearing a jacket backward to a formal event just left everyone confused. This look is still one of her most puzzling choices.
Tilda Swinton
Tilda Swinton is known for unique and daring fashion, but this lumpy velvet gown looked more like a bedsheet than a red carpet dress. Even fashion-forward stars can have a wardrobe misstep.
Whoopi Goldberg
Whoopi’s 1993 Oscars outfit had a spooky, Count Dracula-inspired look that’s still talked about today. She designed it herself—no stylist involved—and it clearly showed. This one tops many worst red carpet outfit lists.
Charlize Theron
Charlize Theron usually looks flawless, but this Dior gown with oddly placed roses was a rare miss. It’s surprising to see a luxury brand like Dior make a design choice that ended up being this awkward.
Hilary Swank
Hilary Swank’s gown looked more like a high school prom dress than a Hollywood statement. The short slip under the sheer overlay made a Dior gown look almost cheap. Not the elegance we expect from the red carpet.
Geena Davis
Geena Davis wore a high-low bubble dress with black straps, sheer tights, and long gloves to the 1992 Academy Awards. The whole look screamed runaway Vegas bride—and not in a good way. Too many clashing elements made this outfit one of the worst red carpet appearances of the decade.
Lady Gaga
Lady Gaga’s red carpet gloves in 2015 went viral for all the wrong reasons. People compared them to oven mitts, cleaning gloves, and even Mr. Krabs’s claws. Gaga is known for bold fashion, but these gloves stole the spotlight—in the worst way.
Kim Kardashian
The 2015 MET Gala theme was “China: Through the Looking Glass,” and Kim Kardashian showed up in a nearly see-through gown with crystals and feathers. While she turned heads, many felt her look missed the theme completely.
Bjork
Bjork’s swan dress, designed by Marjan Pejoski, remains one of the most talked-about red carpet outfits ever. It was so unique that it became a fashion moment—for better or worse. One of the two dresses was later sold for $9,500.
Kim Kardashian
Kim Kardashian wore a 1998 Thierry Mugler vintage gown to the Hollywood Beauty Awards. The dress had a thigh-high slit and bold cutouts, showing plenty of skin. While it didn’t malfunction, many were on edge wondering if it might.
Melissa McCarthy
Melissa McCarthy is usually stunning in bright gowns, but her gray David Meister dress in 2013 fell flat. It didn’t flatter her figure or her vibrant personality, making it one of her least memorable red carpet moments.
Jennifer Lopez
Jennifer Lopez usually nails the red carpet, but in 2010, her Armani gown came with so much extra material it looked like fabric overflow. The bulky design didn’t match J.Lo’s usual sleek style.
Kate Hudson
Kate Hudson wore a strange fringe neck shawl with a gray gown that made her almost unrecognizable. Usually flawless, Kate missed the mark with this look, proving that even fashion favorites can get it wrong sometimes.
Angelina Jolie
Angelina Jolie is now known for her classy style, but back in 2000, she arrived at the Oscars looking like a gothic princess. Her all-black dress and emo vibes were hard to ignore—and let’s not even talk about that awkward moment with her brother. Thankfully, her fashion sense has evolved.
Susan Sarandon
Susan Sarandon wore a shiny gold Dolce & Gabbana gown to the 1996 Oscars that made her look more like the award than a nominee. While bold, the outfit reminded everyone of the Academy Award statue—and not in a good way.
Demi Moore
Demi Moore shocked everyone by wearing a self-designed outfit that included spandex bike shorts, a metallic floral wrap, and a corset. This odd mix made her one of the top names on the list of worst dressed celebrities at the Oscars that year.
Kate Winslet
Kate Winslet’s first Oscars appearance featured a shiny pink gown that looked more like spilled Pepto-Bismol than red carpet glam. Even though fashion in the ‘90s was different, this color choice was not a winner.
St. Vincent
St. Vincent wore a bold Saint Laurent creation to the 2018 Oscars that looked more like runway art than wearable fashion. With its strange shape and dramatic flair, it left fans wondering why this was chosen for a real-world event.
Thalia
Thalia’s flowing, scarf-like gown looked like a magical fairy costume. While dreamy, it seemed risky—one wrong step and there could have been a serious wardrobe malfunction. Thankfully, she avoided any mishaps.
Juliette Binoche
Juliette Binoche wore an outfit that used way too much crushed velvet. While she won an award that night, her dress did not win any style points. This look is often remembered as one of the Oscars’ biggest fashion mistakes.
