Hollywood and high fashion collide at the Metropolitan Museum of Art's Costume Institute Benefit Gala every year. The annual event leads to inevitable fashion misses when the stars rock things so unconventional that they don't translate to the masses. And then there are the stars who opt for things so dangerously bold that they end up experiencing wardrobe malfunctions. As the 2021 Met Gala approaches on Sept. 13, Wonderwall.com is rounding up some of those crazy red carpet moments, starting with Jared Leto's contribution… One of the wackiest looks on the 2019 Met Gala red carpet came from Jared Leto, who interpreted the "Camp: Notes on Fashion" theme in this Gucci getup while toting around… his own head. Yep, the actor arrived in a red gown and carried a replica of his noggin after pulling a similar stunt during the Gucci fashion show earlier that year.
Keep reading for more crazy fashion and whoops moments from Met Galas past…
Katy Perry's 2019 Met Gala look involved turning herself into a human chandelier! The pop star arrived in this lighting-inspired look — complete with candlesticks around her head and waist — by Moschino. Creative director Jeremy Scott designed the very unique ensemble, which certainly did fit the year's "Camp: Notes on Fashion" theme.
A dress that went down in infamy! While pregnant with daughter North West, Kim Kardashian attended the 2013 Met Gala in this floral Givenchy design by Riccardo Tisci that included matching gloves. The internet wasn't kind to the look, quickly turning it into memes and making negative comments about the all-over print.
Rita Ora had a wardrobe malfunction at the 2014 Met Gala. The singer sported an ethereal Donna Karan gown that had an accompanying super-high slit, which resulted in her flashing her unmentionables on the red carpet.
Solange Knowles' 2015 Met Gala look raised eyebrows and inspired plenty of memes. The singer and performance artist arrived in a Giles dress that channeled intergalactic space fashion more than any relatable, down-to-earth style.
The all-time strangest accessory ever seen at the Met Gala? That has to go to Jaden Smith and his portable hair: He donned a sleek Louis Vuitton getup while clutching his old dreadlocks, which he'd cut off for a film role, so he opted to carry them along to fashion's biggest night in 2017. One more funky addition to his look that year? Jaden donned a grill over his teeth.
Rihanna's 2015 Met Gala dress spawned 1,000 memes. The yellow Guo Pei creation might have looked a bit like a pizza, but its high-fashion vibe went perfectly with the theme that year — "China: Through the Looking Glass."
Even Anna Wintour makes a fashion misstep every now and then. The Vogue editor attended the 2008 Met Gala in this silver Chanel number, which we guess was an attempt at embracing the "Superheroes: Fashion and Fantasy" theme but left us seeing more of an intergalactic snail than anything else.
Madonna must have been feeling nostalgic when she wore this to the 2009 Met Gala. The superstar sported an '80s-inspired ensemble by Louis Vuitton but the wacky combination missed the mark. Between the ruched minidress and its puffy skirt, the black thigh-high boots, the fingerless gloves and that top knot secured with what appeared to be a wired scrunchie, it screamed hot mess.
It's a miracle that Anja Rubik got through the entire 2012 Met Gala without a wardrobe malfunction caught on camera! The stunning model rocked a dangerous dress by Gucci that featured the highest slit we've seen, well, ever!
Well, Amber Valletta certainly turned heads at the 2004 Met Gala. The theme was "Dangerous Liaisons: Fashions and Furniture in the 18th Century," so we have to give her props for nailing the time period in this bizarre combo of a gold corset by Maggie Norris and a multipatterned and skirt by John Galliano. Her enormous powdered hairstyle and flower prop were just icing on the Marie Antoinette-inspired cake (that we don't want to eat)!
Marc Jacobs wore his own design at the 2012 Met Gala themed "Schiaparelli and Prada: Impossible Conversations," and we're assuming talking him out of this getup was one of those impossible conversations. The designer donned a long, sheer black lace shirt-turned-dress that showed off his underwear. The pulled-up black socks and chunky buckle-adorned loafers just added another odd element to the wacky ensemble.
Lupita Nyong'o raised eyebrows at the 2014 Met Gala in this Prada confection. The year's theme was "Charles James: Beyond Fashion" — and she certainly went above and beyond in this brown and green feather-covered fishnet design!
Who could forget this headpiece?! Sarah Jessica Parker attended the 2015 Met Gala in an extravagant Philip Treacy hat that exemplified the "China: Through the Looking Glass" theme. The more low-key dress was her own design in collaboration with H&M.
As an ode to the designer being recognized that night, Alexander McQueen, Naomi Campbell wore one of his creations at the 2011 Met Gala. The odd white gown featured panels of fabric and gold accents but it looked more like shredded toilet paper than couture.
Freida Pinto wore a Chanel creation fresh off the runway at the 2011 Met Gala, channeling menswear with a feminine twist. Though it was high fashion, it didn't translate to the street and made her look more wacky than stylish.
Jessica Alba looked more like a prom-goer than a movie star when she attended the 2009 Met Gala. The actress wore a Jason Wu jeweled creation with black tights and heels — and the look ended up being a major flop that year.
Zoe Kravitz bared more than she bargained for when she wore this slinky crimson Michael Kors gown. The super-high slit resulted in some photographers catching the wrong angle, which meant Zoe showed off her underwear at the 2014 Met Gala.
While the Gucci suit was super-stylish, the strange addition will.i.am sported on his head at the 2016 Met Gala left us befuddled: a face visor that served no obvious purpose.
Maybe Diane von Furstenberg's take on the "Manus x Machina: Fashion in an Age of Technology" theme was an homage to Snapchat? The legendary designer wore butterflies on her head that looked like a Snapchat filter come to life atop an otherwise simple black-and-white sleeveless dress in what can only be called a very odd Met Gala 2016 addition.
Those high slits are dangerous! Sarah Jessica Parker wore this Giles Deacon gown to the Met Gala in 2013, and its scandalously high slit inevitably showed off a little too much when she posed a certain way. Maybe she should have gone with even taller plaid velvet Louboutin boots?
Bright and shiny aren't exactly the right vibe when it comes to stunning on fashion's biggest night. Musician Grimes attended the 2016 Met Gala in this brightly colored frock by Louis Vuitton, which looked more Coachella casual than couture. Coupled with her messy, unwashed, colorful hair and chunky mismatched purse, it's safe to say Grimes was one of the worst and wackiest dressed stars that year.
Katy Perry certainly made a splash at the 2017 Met Gala when she showed up in this Maison Margiela "Artisanal" look designed by John Galliano. The pop star donned the embroidered red wool coat over a matching red tulle and silk chiffon gown embellished with a satin ribbon for extra drama and accessorized with an insane headpiece, complete with a sheer red veil emblazoned with the word "witness" and adorned with silver embellishments. At the very least this confusing look was somewhat on-topic for the night — that year was all about avant-garde looks, as the theme was "Rei Kawakubo/Comme des Garcons: Art of the In-Between."