There have been an abundance of celebrity Hindenburgs throughout the years — fashion and grooming choices that crash and burn in front of millions of flashbulbs and gawking eyes on the red carpet and beyond, leaving everyone wondering, “WTF where they thinking?” Sometimes it’s what stars are wearing — or not wearing — that catches our attention, other times it’s an unfortunate hair style, and occasionally it’s even a regretful nip and tuck. And often? The mistakes enter pop culture lore and live there in perpetuity. On this list, you’ll see some of the biggest style derps, blunders and overall fails in recent memory. Join us as we stroll down this bumpy Memory Lane, won’t you?
Britney Spears, Justin Timberlake
At the 2001 AMAs, then-”It Couple” Britney Spears and Justin Timberlake committed the fauxest of pas: They each wore head-to-toe denim ensembles, otherwise known as Canadian tuxedos.
With her choker and strapless dress and his cowboy hat and blazer, they looked ready for a rodeo. It was matchy-matchy at its absolute worst.
I'm including this one on the list because I shouldn't be biased (but inevitably I always will be when it comes to my dream artist).
As a journalist, and scientist, here are the facts:
1. People consider this to be a horrendous fashion mistake.
2. People are not necessarily very smart and the symbolism of this act flew way over their heads.
3. Not Smart people need to STFU.
You know it. You’ve seen it. You’ve mocked it.
Kate Gosselin‘s hair, which was flat-ironed straight in the front and short and spiky in the back, was an abomination to all that is follicular.
Sarah Jessica Parker
Sarah Jessica Parker could have intercepted radio signals with the ridiculous Philip Treacy hat she wore to the London premiere of the first ‘Sex and the City’ movie in 2008.
While ornate hats are all the rage in the UK, this flowers-and-butterfly concoction added about four inches to the petite star’s height. SJP is known for her edgy fashion sense, but this topper didn’t earn her any accolades for risk-taking.
Actress Rose McGowan was dating Marilyn Manson when she wore this “dress” — and calling it that is being incredibly generous — to the 1998 VMAs.
Back before she rendered her face nearly unrecognizable, the ‘Charmed’ star let it all hang out porn-star style, wearing a g-string and little else save some mesh and sparkly dental floss.
Long before she was Mrs. Kutcher (on Twitter, at least), Demi Moore wore one of the worst dresses in Oscar history — and she even took credit for designing it herself.
Her get-up for the 1989 ceremony featured a bustier with bike shorts. And even though they were made of velvet instead of spandex, that did nothing to class ‘em up. What’s more, the skirt, which appeared detachable, seemed to be some sort of bedspread-like fabric.
Snooki‘s pouf aka beehive was the equivalent of the teased and Aqua Net-spackled bangs of the ’80s.
Snooki takes pride in being a guidette, and since she’s petite, she probably liked adding a few inches with hair height. It’s a shame, since her silky locks ended up looking like rat’s nest.
Was she storing weed or lip gloss in there? It’s really the only logical reason we could come up with for that knot atop her noggin.
Bjork has always been quirky with her music, but her fashion sense at the 2001 Oscars was more ugly duckling than beautiful swan.
The infamous “dead swan” dress was so weird that we wouldn’t have been shocked if the vigilant folks at PETA called for a cease-and-desist. Hell, they may have even asked her to wear mink instead of this frock.
While it was a fail at the Oscars, it’s gone on to have an endless life as inspiration for countless Halloween costumes and has been mocked in movies and on TV shows (including the 2001 Emmys, where host Ellen DeGeneres put her own spin on it).
Britney Spears 2002 VMAs dominatrix get-up, which was a little bit slutty, a little bit Village People and a whole lotta trashy, turned as many heads as that time she made out with Madonna.
The only thing missing here was a riding crop and some candle wax.
BDSM chic? We get it. BritBrit was at the apex of her Lolita phase here and was milking it for all it was worth. But she was doing her best impression of a bar-back at one of those dungeon-like sex clubs
Joan Rivers is a high-ranking member of ‘The Fashion Police,’ but someone shoulda called the cops on her for the feathery mess she wore to the 2003 Emmy Awards.
Between the Big Bird-ish plumage and the Morticia Addams sleeves and hemline, we’re not sure what she was thinking here.