By Megan Riedlinger
8:22am PDT, Apr 24, 2018
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 2018 Met Gala approaches, Wonderwall.com is rounding up some of those crazy red carpet moments, starting with Solange Knowles. The star attended the 2015 Met Gala in a Giles dress, channeling more of an intergalactic space fashion moment than a relatable, down-to-earth style. Keep reading for more…
RELATED: Cutest couple moments from Met Galas past
What girl doesn't want to be a Disney princess? Katie Holmes is among the majority, but unfortunately, she picked the wrong time to show her love of a certain animated beauty when she attended the 2014 Met Gala. Channeling Belle from "Beauty and the Beast" in this bright yellow Marchesa number, Katie sparkled but looked a little out of place.
RELATED: Celebrity kids all grown up
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-theme 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."
RELATED: The Met Gala's most buzz-worthy looks of yesteryear
The all-time strangest accessory ever seen at the Met Gala? That has to go to Jaden Smith, who donned a sleek Louis Vuitton getup while clutching his old hair. He'd recently cut his dreadlocks 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 Guo Pei yellow 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 for the big event, but its wacky combination missed the mark. Between the ruched minidress and its puffy skirt, the thigh-high black boots, the fingerless gloves and that top knot (is that a wired scrunchie?!), it screamed hot mess.
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 multi-patterned and colored 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!
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.
Who could forget this headpiece?! Sarah Jessica Parker attended the 2015 Met Gala in this 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.
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.
Supermodel Karolina Kurkova had a message for everyone at the 2005 Met Gala. The blonde stunner wore a white Viktor and Rolf gown emblazoned with the words "I Love You" to the big event.
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.
It's a miracle that Anja Rubik got through the entire 2012 Met Gala without a wardrobe malfunction! The stunning model rocked a dangerous dress by Gucci for the event, which featured the highest slit we've seen, well, ever!
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 to the big event — and the look ended up being a major flop that year.
Blake Lively opted for this unfortunate frock at the 2011 Met Gala. That year, the actress wore Chanel, but the drapey nude look was a major departure from the star's normally lauded style.
Kim Kardashian West suffered a wardrobe malfunction at the 2014 Met Gala. The star looked pretty in this Lanvin look on the red carpet, but her high slit ended up showing off a little too much later in the evening.
Kristen Stewart dared to go bare at the 2010 Met Gala. That black Chanel creation landed her on some worst dressed lists that year thanks to its wonky neckline and unfortunate sheer skirt. K-Stew's thrilled expression didn't exactly help either.
He might have been attempting to put himself on the best dressed list, but some disagreed with Andre Leon Talley's look at the 2011 Met Gala. The famed fashion editor put a royal blue shawl over his Ralph Lauren suit for an unconventional red carpet look.
Former Food Network chef Sandra Lee attended the 2013 Met Gala but clearly misinterpreted the concept. That year, the Costume Institute Gala's theme was "PUNK: Chaos to Couture." While the foodie got the memo to wear black, we don't exactly see anything punk about all those ruffles.
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. It seemed to be a face visor that he donned for no real reason.
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 higher plaid velvet Louboutins?
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.
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.
