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2025 - Joy Villa -

We’re not sure where to even begin with this one. The singer-songwriter chose a crypto-inspired gold dress with $WIF accessorizes, which included an oversized necklace featuring a dog in a knitted beanie. Topped off with a red hat saying ‘The hat stays on,’ as an obvious nod to her new president, for whom she has shown enormous support, this bizarre combination has to have been the worst look on the carpet.

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2025 - Bianca Censori -

It’s hard to know if Bianca Censori should really be on this list, as she technically didn’t wear much at all. The model and wife of Kanye West showed up in a floor-length fur coat, until, following a nod from West, she dropped it to the floor to reveal one of his own designs, which was completely see-through. Taking sheer to the next level, this mini dress quite literally revealed all...

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2025 - Lady Gaga -

Lady Gaga was definitely calling all her Little Monsters with this gothic look. Whether it’s weird or wonderful, we’re not sure. But this high-neck, long-sleeve, all-black Vivienne Westwood gown became even more iconic when decorated with vintage Tiffany & Co. jewels and topped with the most severe haircut of the night.

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2025 - Jaden Smith -

Jaden Smith decided to show up to the 2025 Grammys dressed as a castle. To be precise, he wore a black suit with a matching foam castle covering his whole head, with a circle cut out for his face. The Grammy nominee didn’t explain why he showed up as if he were attending a fancy dress competition, but then again it was Louis Vuitton, so maybe we can forgive him!

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2010: Beyoncé -

This pale pink, zippered gown by fashion designer Stephane Rolland was probably a good idea at the time. But it's a heavy and clumsy choice.

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2020: Billy Eilish -

A custom Gucci look with matching nails? More like creepy, weird, and scary poster child for late-adolescent angst. But hey, that works too.

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2014: Pharrell Williams -

Can anybody remember the Royal Canadian Mounted Police being asked to supervise male fashion at the 2014 edition of the Grammys?

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2012: Nicki Minaj - Here's what you get when you cross a nun with Little Red Riding Hood.

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2019: Ashanti -

Now here's a good idea. Why book a hotel room when you can bring along your own sleeping bag?

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2017: Carrie Underwood -

Sheer, lacy, and with a sequin collar. So far, so good. But what's with the peekaboo cleavage?

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2013: Florence Welch - It hurts just imagining her trying to squeeze into that dress. And what's the inspiration behind this Givenchy outfit? Green hornet or swamp crocodile?

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2019: Kylie Jenner -

How to model a fashion straight jacket, with little room to maneuver.

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2017: Katy Perry - Glossy linoleum meets feather duster? Pairing these two completely opposing fabrics just has "no" written all over it.

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2012: Robyn - The minimalist, white outfit isn't too bad. But do you think she realizes that her skirt is topped by a mullet?

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2015: Kim Kardashian -

It may say Jean Paul Gaultier on the label, but the reality is we all know a deluxe bathrobe when we see one.

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2018: Sam Smith -

Sharp suit or military fatigues? A rather uniform fashion sense if ever there was one.

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2010: Imogen Heap -

It's amazing how much influence Tim Burton has on red carpet fashion.

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2017: Santigold - A bubblegum-pink dress with a three-headed serpent uncurling over her chest. Is the singer-songwriter serious?

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2019: Meghan Trainor -

Pantsuit? Nearly. Elvis Presley jumpsuit? Definitely.

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2011: Miley Cyrus -

This Roberto Cavalli snakeskin number doesn't know whether to stay on or slither off.

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2013: Jennifer Lopez - This Anthony Vaccarello outfit doesn't quite cut it. Mini skirt or ball gown? You choose.

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2017: CeeLo Green - CeeLo's alter ego looks ready for some kind of futuristic, other-worldly battle in this golden getup.

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2014: Madonna -

Her penchant for menswear is well known, but here she looks like an undertaker.

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2015: Ariana Grande -

This gown looked stunning, that is until someone accidentally spilled silver nail polish over it.

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2016: Kacey Musgraves - The same galaxy-inspired colors and patterns on this gown are often seen decorating children's lunchboxes.

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2020: Lana Del Rey -

Here's how to look totally underwhelmed for such an overwhelming event.

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2015: Rihanna - The only thing that comes to mind when looking at this dress is the nursery rhyme 'Little Miss Muffet.' But instead of the spider scaring people off, it's the dress.

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2020: Ben Platt -

The latest harlequin look, or borrowed golf sweater?

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2015: Maddy Ziegler and Sia - Oversized blazers and giant wigs. Yep, it's the Ziegler & Sia show.

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2011: Cyndi Lauper -

She might be having fun, but what's with the black road-warrior look?

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2018: Jaden Smith -

The problem with being young is that coordination just goes out of the window. 

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2013: Esperanza Spalding - There are several reasons why this dress is a fashion nightmare, starting with, well, the dress itself.

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2012: Fergie - If her inspiration was a traffic cone, then she pulled it off big time dressed in this oversized lace and blinding orange dress. Let's not even talk about the black granny panties.

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2011: Hayley Williams - Is her Jeremy Scott dress 1920's flapper or pink tutu? Not sure, but the matching hair and eyebrows are interesting.

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2011: Nicole Kidman -

Her strapless mermaid dress by Jean Paul Gaultier appears rather drab. And the rows of gathered ruffles tend to sink the outfit.

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2020: Sophie Turner -

A sequin top minidress may work at a teenager's birthday party, but impressing on the red carpet requires a little more finesse. And why is Joe Jonas looking so glum?

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2012: Kate Beckinsale -

This cream Zuhair Murad mini dress nearly worked. But it was the black detailing that looked odd. Aren't you supposed to wear a belt around the waist?

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2018: Sarah Silverman -

A black shapeless Maggie Marylin dress and Jimmy Choo combat boots. Chic-goth perhaps, but it's the pale yellow rose that catches everybody's eye.

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2020: Chris Brown -

No shirt, no jacket, and no tie. Just two-tone hair and a striped baggy jumper. Sorted!

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2018: Lady Gaga -

A black and white lace catsuit paired with a billowing black skirt. Fancy funeral or fashion faux pas?

See also: Funny celebrity moments on the red carpet

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