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Alright, buckle up! We’re diving right into some of the craziest, most head-scratching fashion moments from the 2026 awards season. Trust me, you’ll want to see these and maybe double-check your eyelids afterward.

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#1

Heidi Klum’s Latex Shock

Heidi Klum’s Latex Shock

Amy Sussman/Getty Images , Amy Sussman/Getty Images Report

Heidi Klum showed up to the big music awards wearing a latex gown that looked like she forgot to put on clothes. It hugged every curve and had all the risqué details - and folks on social media were basically like, “Uh no.” Some called it ugly, while others just wondered if it was Halloween in March.

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    #2

    Chappell Roan’s Bare-It-All Dress

    Chappell Roan’s Bare-It-All Dress

    Amy Sussman/Getty Images , Gilbert Flores/Getty Images Report

    Chappell Roan really brought the shock factor to the Grammys. Her dress was basically just a few rings and some art painted on her body. People were not here for it, calling it “too much” and asking when this trend will end. Spoiler: probably never.

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    #3

    Jenna Ortega’s Spooky Vibes

    Jenna Ortega’s Spooky Vibes

    Amy Sussman/Getty Images , Amy Sussman/Getty Images Report

    Jenna brought some serious Wednesday Addams energy with a black, skin-baring look that had fans dividing opinions. Some said creepy, some said Halloween décor, and others wondered if she’d had a drastic makeover. Let’s just say, it wasn’t your typical awards glow-up.

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    #4

    Gwyneth Paltrow’s Leg Show

    Gwyneth Paltrow’s Leg Show

    Arturo Holmes/Getty Images , Christina House / Los Angeles Times via Getty Images Report

    Gwyneth crashed the Oscars with a gown that looked normal ... until you saw the sides. Giant cutouts showed off her entire leg and some sparkly sheer pants underneath. Some called it a wardrobe malfunction waiting to happen, and honestly, we kinda agree.

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    #5

    Emma Stone’s Butter Yellow Gamble

    Emma Stone’s Butter Yellow Gamble

    Jesse Grant/2026GG/Penske Media via Getty Images , Kevin Mazur/Getty Images Report

    Emma Stone went butter yellow with a two-piece outfit that felt a little too casual for the Golden Globes. Fans were divided on whether it was trendy or just messy, with some wondering if her stylist had a bad day.

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    #6

    Jennifer Lawrence’s Floral Fail

    Jennifer Lawrence’s Floral Fail

    Monica Schipper/Getty Images Report

    Jennifer Lawrence decided to go floral with scary cutouts at the Golden Globes. Fans loved her, but not the dress, calling it desperate for attention and wondering if clothes were optional now.

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    #7

    Mindy Kaling’s Half-Done Dress

    Mindy Kaling’s Half-Done Dress

    Neilson Barnard/Getty Images Report

    Mindy rocked a semi-velvet, semi-sheer dress that had people scratching their heads. It looked like they started making it then got bored. The top had fans saying "okay," but the bottom was a big nope.

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    #8

    Teyana Taylor’s Anatomy Lesson

    Teyana Taylor’s Anatomy Lesson

    Neilson Barnard/Getty Images Report

    Teyana’s dress screamed drama with its body-like design - nipples and belly button included. Said some? Um, no. Even if the craftsmanship was wild, people just couldn’t get past the anatomical vibe.

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    #9

    Miley Cyrus’s ‘Not My Vibe’ Look

    Miley Cyrus’s ‘Not My Vibe’ Look

    Kevin Mazur/Getty Images , Amy Sussman/Getty Images Report

    Miley’s black sequined gown with giant sunglasses made some fans do a double-take, wondering if they’d switched the TV to a Cruella de Vil marathon by mistake. Not everyone was on board with this vibe.

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    #10

    Olivia Rodrigo’s See-Through Surprise

    Olivia Rodrigo’s See-Through Surprise

    Jerritt Clark/Getty Images Report

    Olivia went vintage sheer with a lace mini dress that showed her matching underwear. Fans weren’t sure if it was a bold move or a fashion oops, and some joked it gave them flashbacks to Chappell Roan's more daring look.

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    #11

    Anya Taylor-Joy’s Romper Rumble

    Anya Taylor-Joy’s Romper Rumble

    Karwai Tang/WireImage , Neilson Barnard/Getty Images Report

    Anya showed up in a sheer romper that had people wondering: is this a romper or underwear? Paired with a wild headpiece, her outfit got a mix of “gorgeous” and “what even is this?” and some cheeky jokes about missing dresses.

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    #12

    Jenna Ortega’s Torn-Up Slip

    Jenna Ortega’s Torn-Up Slip

    Amy Sussman/Getty Images Report

    Jenna was back with another risky look - a torn ivory slip dress that had people wondering if this was 'bedroom ready' or just laundry day gone wrong. Some joked it looked like it came from Great Grandma’s attic after a mouse party.

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    #13

    Emilie Livingston’s Pantsless Party

    Emilie Livingston’s Pantsless Party

    Taylor Hill/FilmMagic , Lionel Hahn/Getty Images Report

    Emilie showed up to the Vanity Fair party rocking a glittery black leotard with sheer tights that left... well, her booty kind of out in the open. Some called it cringe-inducing, others just couldn’t look away and wondered if any boundaries remain.

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    #14

    Ariana Grande’s Cake Dress

    Ariana Grande’s Cake Dress

    Kevin Mazur/Getty Images , Matt Winkelmeyer/GA/The Hollywood Reporter via Getty Images Report

    Ariana went glam in a black dress that some said looked like a birthday cake gone wrong. Fans loved her usual glam but weren’t feeling this dress - calling it a mismatch and questioning if she'd borrowed her mom’s dress by accident.

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    #15

    Kesha’s Met Gala Mix-Up

    Kesha’s Met Gala Mix-Up

    BACKGRID Report

    Kesha showed up to the Grammys afterparty looking like she was ready for the Met Gala - with a sheer white outfit topped off by a faux-fur collar and a gold crown. Some called it mystical, others said it looked cheap and messy. Definitely a love-it or leave-it moment.

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    #16

    Justin Bieber’s ‘Just Rolled Out of Bed’ Look

    Justin Bieber’s ‘Just Rolled Out of Bed’ Look

    Jerritt Clark/Getty Images , haileybieber Report

    Justin Bieber went casual to a Grammy afterparty - think open hoodie with no shirt underneath and baggy jeans showing some pink boxer briefs. Fans were baffled and wondered if he got dressed in the dark or just gave up.

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    #17

    Ethan Hawke’s Marching Band Moment

    Ethan Hawke’s Marching Band Moment

    JC Olivera/Variety via Getty Images Report

    Ethan Hawke showed up looking like he escaped from a marching band gig or maybe a pirate show. His Dior outfit had people debating if he was a swashbuckler, matador, or just really committed to a costume party.

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    #18

    Chloé Zhao’s Funeral Vibes

    Chloé Zhao’s Funeral Vibes

    Mike Coppola/Getty Images Report

    Chloé showed up to the Oscars looking like she was headed to a funeral - with a black ruffled dress and veil that had people asking if she was mourning the cancellation of something (hint: Buffy). Fans called it witchy and totally off for an awards party.

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    #19

    Kim Kardashian’s Gold Glitter Disaster

    Kim Kardashian’s Gold Glitter Disaster

    Neilson Barnard/Getty Images , Daniele Venturelli/WireImage Report

    Kim dazzled in a gold sparkling gown fresh from Milan Fashion Week... but her hair? Not so much. Fans loved the dress hugging every curve but agreed the hair looked like it was fighting for attention and losing.

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    #20

    Benny Blanco’s High School Casual

    Benny Blanco’s High School Casual

    Phillip Faraone/Getty Images Report

    Benny Blanco rocked some seriously casual vibes at an afterparty - brown boots, socks, shorts, a pink hoodie, and a brown jacket. Social media was like, "Who dressed Benny?" with many agreeing it looked like a hipster teen’s outfit gone wrong.

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    #21

    Paris Hilton’s Golden Statue Look

    Paris Hilton’s Golden Statue Look

    parishilton Report

    Paris came to the party looking like a shiny golden award herself in a skin-tight sequin gown with a massive diamond choker. Some thought the mixed metals were a bit much and called the look a shiny nightgown gone matronly.

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    #22

    Kylie Jenner & Timothée Chalamet’s Stylist Fail

    Kylie Jenner & Timothée Chalamet’s Stylist Fail

    Neilson Barnard/Getty Images Report

    Kylie and Timothée hit the Oscars afterparty in contrasting black-and-white looks, but fans weren’t loving the vibe. Kylie’s feathered train and Timothée’s all-white leather suit got roasted as a mess, prompting lots of “Who styled these two?” questions.

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