Some Celebrities that Made Epic Fashion Mistakes

By Arie

Celebrities have fallen victim to fashion faux pas. These fashion choices are questionable to say the least and we wish we could just forget about them, but we can’t. We bet these stars feel the same way. While celebrities are known for their style, these outfits are iconic for all of the wrong reasons. You won’t believe some of these fashion fails.

Cameron Diaz

While Cameron Diaz is pretty well known for her California laid-back looks and minimalistic style, this one is even a bit too casual for us. Granny-chic is totally trendy now, but this pink off-the-shoulder slouchy sweater is a bit too cutesy for our taste. Just look at the tacky bow detail and one lace sleeve.

Cameron Diaz's Too Cutesy 

Plus, the bright pink sandals and embellished clutch don’t quite match the vibe of the entire outfit. You can do better Cameron!

Too Much is Going On In This Outfit

Sarah Jessica Parker became a style icon as Carrie Bradshaw in Sex and the City and we lived for her designer outfits in the series. On the red carpet, she always slays with fashion forward looks, so that’s why we could hardly recognize her in this outfit.

Sarah Jessica Parker

Sarah Jessica Parker became a style icon as Carrie Bradshaw in Sex and the City and we lived for her designer outfits in the series. On the red carpet, she always slays with fashion forward looks, so that’s why we could hardly recognize her in this outfit.

Too Much is Going On In This Outfit

Where do we even start here—there’s just so much going on. Between the fedora, hobo bag, scarf, sunglasses, graphic tee, and cargo pants, she combined so many styles into one mismatched outfit. It’s like she wanted to wear all of her accessories at once.

Reese Witherspoon 

It’s only fitting that Reese Witherspoon wore this outfit for the premiere of Cruel Intentions. Cruel intentions indeed. Witherspoon got her big break in the film, but her outfit for the premiere definitely isn’t fit for a leading lading. It’s just not screaming Hollywood A-lister to us. It’s more saying extra.

Cruel Intentions Indeed

On top it’s totally toga party and on the bottom it’s beachy with the maxi skirt and sandals. At least she’s nailing the Grecian goddess look.

Christina Aguilera

Just Look at Christina Aguilera's Pants

If this look doesn’t scream early ‘00s, we don’t know what does. It’s just so Christina Aguilera it hurts. Between the platinum blonde hair with chunky black highlights and trucker hat to the sleeveless white top and super low-rise camo pants, this is a look.

Just look at the pants—they’re everything. They’re tie-up, camo, plaid, and embellished. What more you could possibly want? At least she’s supporting The Rolling Stones, the performer at this benefit concert, with her armband and hat.

Christina Ricci

Christina Ricci is Definitely Unconventional

Chances are you recognize Christina Ricci as Wednesday Addams in The Addams Family films and the actress is known for playing unconventional, dark characters. Well, this look is unconventional.

You may be thinking the navy matching set with silver floral print isn’t so bad, but to us, it looks like a Halloween costume. And don’t even get us started on the shoes—

they look like tennis balls and they’re pretty dirty. What was she thinking? At least she could’ve thrown on some heels.

Paris Hilton

Paris Hilton was a huge trendsetter in the early ‘00s. We have her to thank for many Y2K staples like low-rise jeans, graphic tees, velour track suits, and denim mini skirts, but this look couldn’t be more opposite from her usual style.

That’s NOT Hot

To be completely honest, she looks more like her mom Kathy in this tweed suit ensemble. Doesn’t the look age her? She’s almost completely covered up which is so not Paris. That’s NOT hot.

Gwen Stefani

Gwen Stefani’s Embodying Grandpa Fashion

We’re not sure we’d “Hollaback Girl” after seeing this outfit Gwen Stefani wore to a gallery opening in the early ‘00s. Stefani’s truly embodying grandpa fashion with the argyle vest and embroidered blazer

Gwen Stefani’s Embodying Grandpa Fashion

Did we mention she’s wearing a skirt over pants—does it get anymore Y2K than that? Well at least the shoes sort of match the look. Don’t worry Gwen, we promise not to speak about this one again.

Britney Spears

Britney Spears's Pink Denim Look

Britney Spears had a major red carpet moment with Justin Timberlake wearing the full denim look at the 2001 American Music Awards. Over 20 years later and we’re still talking about it. While that look was iconic, this denim look leaves a lot to be desired.

Britney Spears's Pink Denim Look 

First of all, we’d like to know where she found pink chaps and pink snakeskin cowboy boots. Chaps are hard to pull off, even if you’re one of the biggest pop stars. And pink and red—really?

Melissa Joan Hart

A Take Your Kids to the Mall Kinda Look

Melissa Joan Hart will always be our Sabrina the Teenage Witch, but this knitted sweater, trousers, and hobo bag combo she wore to the Toys for Tots benefit in 2003 don’t scream red carpet. It’s more taking my kids for a shopping date at the mall than Hollywood actress. And we’re not saying there’s anything wrong with that.

A Take Your Kids to the Mall Kinda Look

Who knows—maybe it was really cold? Perhaps she could’ve thrown on something a bit dressier like a blazer.

Anne Heche

Where do you think Anne Heche was going in this outfit? Chances are you didn’t guess The Sundance Film Festival. The I Know What You Did Last Summer actress Anne Heche showed up to this red carpet event in a trapper hat, jeans, a t-shirt, sunglasses, and sneakers.

Ill-Fitting and Tacky 

Not only was she wearing blue jeans, but the jeans were ill-fitting as they were rolled up at the hem. They also had huge tacky butterflies that scream Limited Too.

Jennifer Aniston

How Did Skirts Over Pants Become a Thing?

Jennifer Aniston became known for playing Rachel Green on Friends and over 25 years later, we still find ourselves recreating some of her iconic looks from the show like the little black dress and pleated mini skirts. It’s safe to say Jennifer Aniston is also a fashionista but this look is just too safe.

How Did Skirts Over Pants Become a Thing? 

There’s nothing exciting going on and we can’t help but wonder how dresses over pants became a thing in the ‘80s.

Drew Barrymores 

Not Appropriate for the Red Carpet

Yet again, just not a look that’s appropriate for the red carpet. Sure, we can see a high school student wearing this outfit, but a movie star to her premiere of Tommy Boy, not so much. Drew Barrymore’s wearing a backpack!

Not Appropriate for the Red Carpet

The whole look is a bit sloppy with the undershirt peeking out underneath the sweater, which has a rip in it, and the belt is holding up the oversized pants. Even the jewelry is a bit kitschy with the beaded necklace and wood bracelet.

Nicole Kidman

Nicole Kidman Looks Outdated

Would you believe this red carpet outfit is just a few years old? Yeah, it’s from the Boy Erased premiere in 2018. Nicole Kidman has us fooled as this purple sparkly dress with sheer panels and a chiffon skirt looks like it came straight from the ‘80s.

Nicole Kidman Looks Outdated 

While Kidman looks flawless in whatever she wears, this dress is really outdated. Plus, it looks like it’s two dresses combined into one since the fabrics don’t quit work together.

Elizabeth Berkleys

Okay, so we all have off days and sometimes we just leave the house in the first thing we find. But when you’re a celebrity, you can’t really do that as paparazzi is always following you around, waiting to catch you at your worst.

Elizabeth Berkleys' Skater Boy Vibes

Saved by the Bell star Elizabeth Berkley may’ve been on her way to brunch with the girls, but on top, she looks like Barney, and on the bottom, she’s giving off skater boy vibes with her baggy jeans and flip flops.

Cher Horowitz

Cher Horowitz Would be Shaking in Her Heels

Alicia Silverstone gave us major fashion inspiration playing Cher Horowitz in Clueless—we’re still recreating the yellow Chanel suit outfit. But we can’t help but think Cher would be shaking in her heels with this outfit.

Cher Horowitz Would be Shaking in Her Heels

The top is doing the most with the argyle and stripes print in hot pink, lime green, and bright orange, and the tassels at the bottom. There’s just so much going on in one shirt.

Kirsten Dunst

Kirsten Dunst's Accessorizing Fail

There’s no doubt that Kirsten Dunst is crazy beautiful, but this look she wore to the premiere of Crazy/beautiful is more fitting for a graduation or bridal shower than the red carpet. While the white lace dress isn’t awful, she’s lost us with the accessories.

Kirsten Dunst's Accessorizing Fail 

The powder blue belt with an embellished sun brooch looks like they ran out of fabric to make the bow even and the shoes don’t quite match the femininity of the dress.

Lil Kim

OMG! Are you seeing a theme here? It’s the dresses on top of pants people. How was this ever fashionable? Lil Kim fell right into this trend and not only did she wear a dress with jeans, she completed the look with a denim jacket. The double denim isn’t working here. Also, take a moment to acknowledge the popped collar. Lol.

Lil' Kim's Denim on Denim

As if this outfit wasn’t already a lot with the flower embellishments, the Louis Vuitton black bag isn’t exactly matching the rest of the rapper’s look.

Madonna

Madonna's Unrecognizable

Who didn’t want to own a Juicy Couture tracksuit back in the day? While we wanted a velour one, we would’ve been happy with any of them. Apparently, Madonna was also a fan.

Madonna's Unrecognizable 

We could barely recognize the “Material Girl” singer in this look that wasn’t the most cohesive. The tracksuit is totally sporty, but the white undershirt is making Madonna look sloppy. Not to mention the sunglasses and slouchy beanie aren’t screaming popstar.

Alanis Morissette

A Rather Frumpy Look

Where do we even start here? While there’s no denying Alanis Morissette is beautiful, this outfit she wore to the Environmental Media Awards in 2003 is rather frumpy.

A Rather Frumpy Look

For one, the shirt looks like a cat or paper shredder got to it and the black dress underneath is completely shapeless, doing absolutely nothing for her figure. To top the grungy look off, the “Ironic” singer threw on a black scarf. As if there wasn’t already enough black.

Neve Campbell

While the Scream actress can do no wrong, this outfit is a real snooze fest. It’s really not red carpet worthy. Neve Campbell’s ensemble she wore to the premier of Hollywood Ending is just so casual with the black cotton top and army green midi skirt.

A Real Snooze Fest

But what’s really catching our eyes is the floor-length denim jacket with frayed sleeves and a hem. Were these ever stylish? We sure hope not.

Julie Benz

Julie Benz is Giving Us Bar Mitzvah Vibes

While we loathed Julie Benz’ Darla on Buffy the Vampire Slayer, we fell in love with Rita on Dexter. But we’re not loving this outfit she wore on the red carpet. It’s giving us Bar Mitzvah guest vibes instead of Hollywood actress.

Julie Benz is Giving Us Bar Mitzvah Vibes

Sure, crochet is really in right now, but a gold crochet top for a film premiere with a blue floral print embellished skirt, isn’t doing it for us.

Sharon Stone

Sharon Stone became known for playing femme fatales and mysterious women, but this black dress is giving us total Rock ‘n’ Roll vibes. Not only is very little left to the imagination, there’s just too much going on in this dress with the sequin, feathers, belt buckles, thigh-high slit, and black panel cutouts.

Less is More

And then there’s the flashy diamond chocker and long necklace and the dramatic black boots. In this case, less is more.

Cindy Crawford

During the ‘80s and ‘90s Cindy Crawford was one of the most popular supermodels—there was rarely a magazine cover or runway she didn’t grace. But this pink strappy midi dress with gold floral lace details and a bright, hibiscus print on the chest is screaming more model off duty.

There's Just Too Much Going On

To be honest, Crawford would look like a million bucks in just about anything she wears, but this outfit isn’t delivering. Yet another example of just too much going on.

Sean puffy Diddy

Sean Combs has changed his name more times than we can keep track of. Puffy Daddy, Puffy, P. Diddy, Diddy—we’re not even sure what to call the rapper anymore. But what we can all agree on is this outfit he wore to the Fall/Winter 2003 Marc Jacobs Fashion Show is wild. Was he part of the show?

Sean "P. Diddy" Combs is Giving Us Everything, Literally

The black leather jacket with fur is a lot and the matching beige beanie, turtleneck sweater, and trousers are making him look like a giant Band-Aid.

Heather Locklear

If this was Coachella, we’d be all for this outfit, but it’s not—it’s the Vogue Fashion Awards Ceremony. Heather Locklear looks like she’s on her way to a rave.

A Coachella-type Look

The sheer top with sequin embellishments, the green sequin neck wrap, and sequin fringe heeled boots with yellow details are more fitting for the Worst Fashion Awards. At least the Melrose Place actress appears to be ready to dance. It must’ve been really fun to pose in this outfit.

Rooney Mara

Did Rooney Mara get secretly married? Well, no. While we could see a bride wearing this white mini dress with embellished floral details to a courthouse wedding, she wore this to the Side Effects film premiere.

Rooney Mara's Courthouse Wedding Dress

At first glance, the dress isn’t too bad, but up close, there’s just too much going on. For starters, what’s going on with the flap on top? Is it a bolero or part of the dress? And there’s heavy floral beading and lace floral details. At least it fits her like a glove.

Gwyneth Paltrow

We can’t help but think celebrities wouldn’t wear a dress like this on the red carpet now. This looks more like a Halloween costume to us. But enough about that.

Gwyneth Paltrow Looks Costume-y

It’s not the dress style that Gwyneth Paltrow she wore to the Sliding Doors film premiere that’s questionable here, it’s the colors which completely wash her out. Plus, the green details make it look like she spilled coffee on her outfit before attending the event.

Lauren Hutton

Model Lauren Hutton became known for the gap in her teeth, but in this look we can’t stop staring at the outfit she wore to the GQ Men of the Year Awards. It’s just so shiny. The whole look isn’t doing anything for her amazing figure and it’s making her look shapeless.

Lauren Hutton's Just So Shiny

Where do we start? The shirt’s sleeves are too short and the pants legs are too short. And the colors completely clash.

Heidi Klum

Most people can agree that Heidi Klum is one of the most beautiful women in the world and the former Victoria’s Secret Angel knows a thing or two about fashion, after all she was the host of Project Runway.

What Would Tim Gunn Say?

We can’t help but think Tim Gunn would roast her in this gown she wore to the amfAR Gala at Fall Winter 2020 New York Fashion Week. While the color is to die for, the dress is completely shapeless and it looks like a bed cover.

Katy Perry

This dress is doing the most. Katy Perry’s ready to fly away at the amfAR Gala in this blue feathered and tulle dress with exaggerated shoulders that look like wings. Again, we’re loving the color, but that’s about all we like about the gown.

Well, We Do Like the Color

If you can manage to stop looking at the feathers, check out the bow and brooch embellishment—it’s a lot. Here’s just another example of less is more.

Faith Hill

If this was a pride gala event, Faith Hill would fit right in. But this was the Oscars and this dress isn’t screaming the biggest night in Hollywood. While we’re sure this colorful ombre pastel gown caught everyone’s attention, it’s not formal enough for the event.

Faith Hill's Ready for Pride

She must’ve been so inspired by her performance of “Somewhere Over the Rainbow”, that she matched her outfit to it. Pretty clever, but still just too casual.

Kim Kardashian

Even throwing up peace signs won’t help this fashion nightmare from the almost always stylish Kim Kardashian. Do you remember when we all used to wear oversized belts over our tops? Belts are supposed to hold up pants—this white one is doing nothing besides for being an eye sore.

Kim, We Expected Better From You

And tunic tops with leggings and hobo bags and oversized sunglasses are so late ‘00s. Kim, we expected better from you.

Once again,Kim Kardashian

Okay, we get it—animal print is totally on trend, but a head-to-toe print outfit is even a bit too much for us. Kim Kardashian really went for it with this cheetah print onesie, matching cheetah print coat, cheetah print gloves, and cheetah print boots at 2019’s Paris Fashion Week. Who even has that much animal print in their wardrobe?

Once Again, Kim Kardashian

Well, Kim does. While the outfit, hugs her body perfectly, the Keeping Up With the Kardashians star is really giving the Cheetah Girls a run for their money.

Celine Dion

In addition to being a pop legend, Dion’s the queen of monochromatic looks. This turquoise one is just one of her many one-color looks, which includes an all red suit and a yellow suit.

Did Celine Dion Join the Blue Man Group?

The outfit is just too much with the fluffy fanny pack, coat, and skirt paired with tights and crocodile thigh-high boots. Even though we love the color, the “My Heart Will Go On” singer looks like she should be part of the Blue Man Group.

Helena Bonham

Oscar winner Helena Bonham has been in some of our favorite films like Harry Potter, Charlie and the Chocolate Factory, and Sweeney Todd: The Demon Barber of Fleet Street, but when it comes to red carpet looks, hers aren’t always our favorite. While we can appreciate that she takes risks with her fashion, she’s a red carpet rebel.

Helena Bow-nham Carter

Off the red carpet, her outfits are just as questionable. The mismatched bows, the star print scarf, the hibiscus print dress, fur coat, and socks and sneakers are definitely a look.

Kendall Jenner

Wow. Just wow. Kendall Jenner is absolutely stunning but in this matching slime green glittery set she wore to the 2020 BRIT Awards after party, she looks like a highlighter. They did say neon’s back in.

Our Eyes Are Hurting

The color is simply just too shocking. Our eyes are hurting just looking at it, so imagine how blinding the look must’ve been in person. The ‘90s style metallic bag isn’t toning down things either. Also, just look at the Cinderella shoes—there’s no way they were comfy.

Jena Malone

We’re so used to seeing Jena Malone as a blonde, that we forgot she used to have dark hair during the early part of her career. You could’ve tricked us into thinking she was part of the catering staff at the premiere of Pride and Prejudice, in which she played one of the leading ladies.

Total Apron Vibes

The dress is giving us total apron vibes with the pockets and Peter Pan collar and the silhouette looks really matronly. Plus, the gray and yellow colors of the dress are just so boring.

Lizzie McGuire

Lizzie McGuire’s Hilary Duff was another Y2K style icon we turned to back in the day. Do you remember when everyone wanted to get their hands on Von Dutch, but only celebrities could afford the “luxury” brand.

Hilary Duff's Pants are a Bit Much

While we’re used to seeing trucker hats with the logo, these low-rise denim and hot pink leather jeans she wore to her Metamorphosis album signing are a bit much. At least this look wasn’t on the red carpet.

Sandy Powell

We’re not going to lie, we excepted more from the British costume designer. Sandy Powell’s known for her work from Shakespeare in Love and The Young Victoria, but a graphic tee with a blue satin suit isn’t cutting it for us.

Is This Sandy Powell or David Bowie?

Did we mention she wore this to the Cannes Film Festival for the premiere of How to Talk to Girls at Parties? In a sea of gorgeous gowns and well-tailored suits, this doesn’t quite fit in.

Dunham’s sister

We’ll let Lena Dunham’s sister take this one. The actress posted on Twitter that her sister said, "It's like the Delia's catalogue made a red carpet dress!" Yep, that pretty much sums it up perfectly.

Not a Girl, Not Yet a Woman

The teal silk ballgown with coral rose print and black trim looks fitting for a pre-teen, but not for the Emmys. While the dress might’ve been a miss, The Girls actress did go away with wins for Outstanding Comedy Series, Lead Actress in a Comedy Series, and Directing a Comedy Series.

Taylor Swift

Taylor Swift has had an epic style transformation during her career. She’s gone from country sweetheart to pop legend, and her red carpet looks have reflected that. She’s now known for bold colors, dramatic silhouettes, and tons of sparkles, but in the late ‘00s she was all about cowboy boots and romantic dresses.

Taylor Swift's Disney Princess Vibes

Such is the case with this gold ballgown she wore to the 2007 Country Music Awards, that’s giving us total Disney princess vibes, but the color is totally off. The night wasn’t all bad as she won Best New Artist.

Iggy Azalea

When Iggy Azalea hits the red carpet you know she’s going to make a statement. Between deep-V dresses, daring cutouts, and thing-high splits, the singer isn’t afraid to take fashion risks. One thing for sure is she always look super sultry.

Iggy Azalea Reminds Us of Our Grandma's Curtains

But at New York Fashion Week in 2014, Iggy wasn’t looking fancy. This black dress with gold embroidery is super safe and it’s reminding us of our grandma’s curtains.

Amber Rose

Amber Rose, you’re not fooling anyone. We’d be able spot you a mile away with your signature platinum buzzcut. But girl, we’re not getting this outfit. As if the watercolor marble print overly structured suit wasn’t already doing the most, what’s with the black lace top underneath?

We Just Don't Get It

The print is already a lot, but as a set, it’s just overwhelming. With the black thigh-high leather boots completing the ensemble, it looks like she’s wearing two completely different outfits. It’s the mullet of looks—business on top, party underneath.

Mary-Kate and Ashley

Oh look—it’s the Olsen twins. And Mary-Kate and Ashley did what they do best at the 2018 MET Gala—twinning. To truly appreciate these outfits for what they are we have to mention the theme of the event was “Heavenly Bodies: Fashion and the Catholic Imagination”.

Mary-Kate Olsen and Ashley Olsen Look Shapeless

While the flowing robe-like gowns perfectly capture their bohemian vibe, they’re pretty shapeless and they’re drowning the sisters’ slim figures. Did they even consider the event’s theme?

Katie Holmes

Katie Holmes is the queen of street style and her cashmere cardigan and bra set she wore a few years ago pretty much broke the internet. But the Dawson’s Creek actress has had a few misses on the red carpet, like most celebrities.

We Guess Yellow IS a Hard Color to Pull Off

Yellow’s a hard color for anyone to pull off and this shade isn’t doing the actress any favors. And that’s not all—the top and skirt are just too casual and ill-fitting for an event celebrating awards season.

Shailene Woodley

There’s just something not quit right about this black floor-length dress with floral details Big Little Lies actress Shailene Woodley wore to The Hunger Games premiere. Besides for the dresses’ flowers being an optical illusion, it looks like it’s missing something in the middle. Maybe the designer ran out of flower print?

At Least it Has Pockets

It also looks like a sack on the actress. Well, at least it has pockets! So, it’s not a total loss.

Justin Bieber

If this was a contest for construction worker chic, Justin Bieber would be the undeniable winner. On top, the “Baby” singer is giving us total doctor vibes and, on the bottom, he looks like a painter with paint splatters all over the pants.

Justin Bieber's Rocking That Construction Worker Chic

While this was clearly his day off, he’s not looking much like a pop star, let alone the “Prince of Pop”. At least he’s wearing a mask!

Lady Gaga

Did you really think we’d make a fashion mistakes list without Lady Gaga? When it comes to style, Lady Gaga isn’t afraid to make a statement and we never know what to expect with her outfits. They all have one thing in common—they’re wild. How can you forget about the infamous meat dress?

It's Totally (Lady) Gaga

While this white mini with 3D structures she wore to the 2008 Jingle Ball is out there, you won’t believe it’s one of her more wearable, toned-down looks. One thing for sure is it’s totally Gaga.

Sandra Bullock

Sandra Bullock is another one of the A-listers who’s known for being America’s sweetheart and while her style is usually on point, this dress isn’t our favorite.

Sandra Bullock's Flower Overload

Bullock wore it to the premiere of Murder By Numbers at the 2002 Cannes Film Festival and there’s just too much happening in the look. There are flowers, ruffles, and mesh cutouts. Safe to say, it’s made many Worst Dressed lists. Are you really surprised?

Rihanna

Wow, this is not the type of outfit we’ve ever worn to the dentist. But for Rihanna, it’s exactly what she wore. We’re getting a headache just looking at the optical illusion, so we can’t imagine this is the best thing to wear for someone who’s holding sharp, metal objects in your mouth.

For an Optical Illusion, This is Great

While white and black is usually chic, we’re not loving the clashing patterns of the checkerboard top and zebra print pants.

Khloe Kardashian

Like her sister Kendall and Kim, Khloe’s made a few bad choices when it comes to clothes. While she looks flawless at awards shows, in her day-to-day life, she’s doesn’t always look super glamorous.

Khloe Kardashian's Outfit is a (Flip) Flop

Sure, there’s nothing wrong with jeans and a t-shirt, but what in the world is going on with these jeans? You’d think she could afford a tailor. Why are they even rolled up like that? And the flip flops aren’t helping make this outfit look any less sloppy.

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