Award shows are often the highlight of the year for entertainment lovers.
A bad look on an important night can go on to haunt stars for years just ask Whoopi Goldberg.
Let’s take a look.
The star wore what can only be described as a semiformal, ultra-girly ballet outfit.
To make an already bad situation worse, Boyle paired the getup with satin pumps with lace wraparound bows.
This outfit is living proof that even the best-loved designers can get it wrong sometimes.
The jumpsuit was an unusual creation from Balmain Couture and certainly wasn’t your average Grammy look.
The shape of it drowned Jenner, who is relatively petite at 5-foot-6.
Unfortunately, the backlash was so intense that it impacted how Goldberg approached fashion moving forward.
It hurt my feelings.
It kept me from dressing up for a very long time.
If this were Awards Show Barbie, she’d be going home empty-handed.
Even so, we have to give the “Twilight” alum props for shaking things up.
Kim Basinger wore a strange bridal look in 1990
We stan a good bridal look.
Though it may have looked like a botched bridal dress, it still gave off wedding ceremony vibes.
The gown came from Basinger’s own vision the actress designed it herself.
Jada Pinkett Smith falls into the latter category.
Back in 1998, he dated “Charmed” star Rose McGowan.
The pair certainly weren’t shy when it came to flaunting their love.
McGowan supported her beau at the MTV Video Music Awards that year, and she wore an eyebrow-raising getup.
The actress sported a black dress that was see-through mesh at the front and black string at the back.
She opted to go braless and wore a black G-string to protect her modesty at least in the front.
“I [wore] that for a reason,” she said (viaMetro).
“It was my first public appearance after being raped.
If you or anyone you know has been a victim of sexual assault, help is available.
Visit theRape, Abuse & Incest National connection websiteor contact RAINN’s National Helpline at 1-800-656-HOPE (4673).
For the Academy Awards in 2020, Wiig donned an interesting bright red dress by Valentino Haute Couture.
Wiig finished off the look with nude pointed pumps and dramatic black opera gloves.
Twain highlighted the black and white coord with a bright red wig.
That said, there’s no doubt Twain’s iconic leopard print outfits look a million times better.
The Italian screen siren took ruffles to the extreme when she made an appearance at the 2009 Academy Awards.
Gardiner was nothing but dedicated to the theme, accessorizing with gold platform pumps and a gold headband.
Gaga wore the shocking look to the 2010 MTV Video Music Awards.
Thurman looked glowing and beautiful, but the gown simply wasn’t up to par.
To make matters worse, Britney paired the in-your-face outfit with black pumps that featured elaborate string detailing.
However, some trends stand the test of time and resurface, while others die a royal death.
Hindsight is 20/20, and it’s become clear that this wasn’t a good look.
Regardless of what was intended, there’s too much going on here.
While we love a good tailoring moment when it hits right, McEntire missed the mark.
Not only was the color and pattern a touch too gaudy, but it was also ill-fitting and chunky.
McEntire paired the look with chunky black pumps and kept accessories fairly minimal with gold brooches and small earrings.
Had it been a different style, this could’ve easily been a win.
In 2023, he showed up to the Grammys wearing a striking multicolored EgonLab jumpsuit.
Its diamond pattern and low-cut square neckline got everyone talking.
It just goes to show that even the best pop stars aren’t infallible when it comes to fashion.
Would you want it any other way?
In 2017, he appeared at the Academy Awards to announce the nominees for best actor.
Keys highlighted her outfit with gold glittery eye shadow.
Many men in Hollywood prefer to go for the classic look, but Redmayne isn’t one of them.
He can often be seen at various events sporting loud, patterned suits.
Sometimes it works, sometimes it doesn’t.
Redmayne toldE!reporter Zuri Hall what influenced his decision to wear the monochrome number.
“I’m colorblind, which is why I’m wearing black and white tonight.
When I wear color, it can be a bit risque.”
Redmayne’s outfit choice sparked a lot of conversation online.
Many praised the actor for taking a risk, while others placed him firmly on the worst-dressed list.
In 1974, actress Edy Williams was known for her skimpy style choices and her sex-kitten persona.
To stay true to form, she turned up at the Oscars wearing a leopard print bikini.
Some other stars also showed a little flesh, including Cher, who wore a barely there pastel gown.
Instead, we were shading ourselves from the glare of her shiny purple silk.
Needless to say, her gown didn’t win any awards, either.
Presumably to accentuate the blue of his ensemble, Rodman wore heavy blue eye shadow.
Rodman’s date for the night, actress Vivica A.
Regardless, at least we can’t accuse Rodman of playing it safe.
While Braxton’s figure was phenomenal, the material didn’t do much in terms of style.
Drescher wore a safe and inoffensive white floor-length maxi gown for the night’s festivities.
And while this may have flown under the radar, her elaborate floral headpiece didn’t.
One of the outfits that divided opinion was the star’s Golden Globes ensemble.
Chalamet had worn several scarves to different events since the release of the Dylan caper.
Some outlets also suggested that he was simply trying to emulate Dylan in all of his bohemian glory.
Diaz’s makeup was grungy with a smoky eye, making her baby blues stand out wonderfully.
However, the dress falls worryingly short of the bar.
The black pants and black shoes combo made her look slightly dowdy.
We’ve all had those!
If things got a little chilly, Crow could wrap herself up in her floor-length blue coat.
We couldn’t help but be boggled.
There were a lot of different elements to digest here, and none of them seemed cohesive.
In 1996, the star rolled up to the Academy Awards wearing an evening gown by Dolce & Gabbana.
Surprisingly, the sunglasses were the only saving grace for some of the photographs.
Diane Kruger made a rare fashion mistake
Diane Kruger is one of Tinseltown’s most radiant stars.
Fans regularly take style cues from her, but it hasn’t always been that way.
Her Golden Globes look in 2005 won few points.
At the time, she was a new up-and-coming actress with only a handful of credits to her name.
As her career progressed, so did her taste.
To add insult to injury, Minelli accessorized with a flash of bright blue in her famous black locks.
For the 2025 Golden Globes, the star wore a velvet suit from designer Loro Piana.
Sunglasses peeped out from underneath the hat’s rim, giving Strong the look of a used car salesman.
It’s a crying shame, but you’re free to’t win them all.
The dress wasn’t just a flashy outfit but also a party trick.
It could change color and even be written on.
Her green chunky pumps stood out like sore thumbs next to the chic playfulness of her dress.
We can’t change fashion history, but we can take notes and remember what not to do.
Every now and then, she still likes to switch things up a little by throwing us a curveball.
In 2015, she attended the Academy Awards wearing a stunning white glittery gown from Azzedine Alaia.
The shape of the dress was undeniably gorgeous and Gaga-esque, with boxy shoulders and a cinched waist.
However, the scene was stolen by Gaga’s enormous red gloves.
We have to admit, this outfit has two halves.
Still, it wouldn’t be Gaga if there wasn’t something slightly unusual involved.
Davis added an extra touch by wearing matching white evening gloves, sheer black tights, and black pumps.
Whatever Davis was trying to achieve, it’s a memorable look but for all the wrong reasons.
Whether the sheerness of the dress was intentional or a camera flash mishap is up for debate, too.
Bates certainly couldn’t be accused of underdressing for the occasion.
We can’t blame her.
Certain rules should be followed, and Travolta threw them all out of the window.
Was it a fashion protest?
We’ll never know.
