30+ Red Carpet Looks From the 2000s We Can’t Get Over

Teen star Hilary Duff walked the red carpet for the 2003 Nickelodeon Kids Choice Awards. She wore an interesting outfit with an embroidered/layered look with funky boots. While we’re not saying it isn’t very nice, we think these pieces would’ve looked better on their own.

Hilary committed the ultimate fashion faux pas by pairing together items that should be worn with a plain top or bottom. We get that the whole point of dressing up is to stand out, but this outfit does little for Hilary other than make us question whether she thought this out on her own or paid a stylist to dress her.

Ashely Olsen, one-half of the famous Olsen twins, showed up to the Nickelodeon Kids Choice Awards in 2004 with her pajama bottoms on! Okay, it’s not really her pajamas, but it sure looks like it. We can’t imagine what she was thinking!

The top half of her body looks elegant, almost formal. The bottom half has us wanting to call the fashion police. We cannot fathom why she would choose baggy pants (in satin!!) as a complement to her top.

Raven Symoné was one of the more relatable child stars of the 2000s, but her outfit at the 2004 Nickelodeon Kids Choice Awards was anything but as she paired an OTT top with a pair of patchwork stiletto-heeled boots.

While we applaud her for at least matching her colors, the outfit is a bit much and would look much better broken down. Raven is known for her funky fashion choices, but this one takes the cake and earns her a night in fashion jail.

Everyone loved Christina Aguilera in her “Dirty” phase. She did an image overhaul and showed the world her raunchy side with a series of barely-there outfits. Her outfit at the 2002 MTV Video Music Awards perfectly exemplifies this new look.

Who knew that a scarf could be so versatile? X-Tina showed us how to transform our winter essentials into a top when she paired it with a short skirt and stiletto-heeled boots. While this isn’t everyone’s cup of tea, it somehow works.

You’d think a billionaire heiress would have many stylists to help her prepare for a glitzy red carpet event. But, as this outfit proves, not even money can buy style as Paris Hilton donned this blue mess to the 2003 MTV Movie Awards.

Ms. Hilton is known for her now trademarked catchphrase, “That’s Hot!” But, we’re here to say that her outfit is anything but hot. It should forever be banished to the back of her closet, never to be seen again.

Beyonce raised more than a few eyebrows at a Superbowl press conference in 2004. She arrived wearing Ugg boots paired with a brown mini and tweed blazer. While we applaud her for sticking to a specific color palette, we’d have mixed it up a bit.

Uggs have a reputation for being rather casual, so perhaps a different shoe would’ve matched her outfit better and added a touch of class to an otherwise cute outfit. Try again, Miss B, because this outfit is not it.

Kim Kardashian is quite easily one of the most glamorous women in the world and is known for her classic yet classy outfits on the red carpet. However, this outfit from a party in 2006 has us wondering what look she was going for.

Satin, fur, denim, and leather are not our first choice of fabrics we’d pair together, but Kim thought it was a good idea as she went for an ice queen look for her red carpet walk. Thankfully, this Kardashian has improved her style over the years!

While we understand that Ashley Tisdale was going for a relaxed, almost pajama-like look on the red carpet for the premiere of Princess Diaries 2 in 2004, we can’t help but shudder at this all-pink ensemble.

Perhaps a pair of white or pastel pink pants would’ve worked better, as these jeans clearly do nothing to pull this outfit together. Congrats on trying to stick with them, Ash, but maybe next time, try to adopt a less-is-more approach to your red carpet outfit.

The Golden Globes pre-event party is usually a less casual affair than the actual ceremony. However, it’s still not the right occasion to wear the cringeworthy Uggs and denim mini combo that was considered a look in the early 2000s.

Seen here at a pre-Golden Globes party in 2003, Nicole Richie looked anything but well put together as she strutted her stuff in a mini and sweatshirt. Let’s hope she glammed up for the main event and left her comfy Uggs at home where they belong!

This one brings us not one, but two fashion disasters of the 2000s in the form of Kelly Osbourne and Avril Lavigne. Pictured here at the 2003 MTV VMAs, the two donned their finest punk outfits in an effort to stand out, and boy did they ever!

From Avril’s lingerie-inspired top to Kelly’s bold t-shirt, there’s very little right with this picture, which obviously turned more than a few heads. We know Avril was the queen of punk for a while and are rather grateful that she swapped this look for a more glamorous, refined dress code in her later years.

Britney Spears has had a few questionable outfit choices over the years, such as this confused combo she wore to the Nickelodeon Kids Choice Awards in 2003. Pairing a cute floral dress with clunky cowboy boots wouldn’t have been our first choice.

We’re hoping that Britney, too, regretted her decision when she saw herself in pictures after the event and that she tossed those boots in the trash where they belong. Come on, Britney! We know you can do better than that!

Do you remember that awful trend of pairing a glam top with jeans and heels? Mischa Barton was clearly a big fan of the style and wore it to the Nickelodeon Kids Choice Awards in 2004.

She rocked the look and inspired many copycat outfits. Young girls everywhere started combining their favorite slinky dresses with bootleg jeans and slinky heels to parties and clubs in the early 2000s. Thanks, Mischa, for the inspiration!

Anne Hathaway combined business with casual for her outfit at the Nickelodeon Kids Choice Awards in 2003. Wearing a crisp white shirt and tie with jeans, the actress looked the part in a fun and neat outfit.

Hathaway is one of few young actresses that should’ve made the best-dressed lists in the early 2000s but was sadly excluded as her outfits were seen as too mature for her age. We’ll give you a high-five for this one, Anne, and hope that more people will look back on this fashion choice as one of the better outfits of the 2000s.

Another early 2000s trend saw young girls pairing flared skirts with jeans and flats to combine casual and glam. While it wasn’t necessarily the worst fashion choice, some didn’t get it right.

Ashely Tisdale makes it onto our list for the second time with her rather, uh, interesting outfit choice for the premiere of the kids’ movie Ice Princess in 2005, leading many to wonder what her aim was when she paired glitter and denim for the event.

We can only thank the powers that be that Rihanna learned how to dress properly after she was photographed wearing this rather confusing ensemble to a party in 2005. While we all love good sweatpants, wearing them with heels is a definite fashion no-no!

Thankfully, Rihanna has grown up and realized her fashion mistake. She’s now known as one of the most glamorous women around and regularly makes headlines for her fashion wins. Don’t worry, RiRi, we still love you despite this little blunder.

There always seems to be one group member with poor fashion sense, but when it’s the entire group, something needs to be said and done! Pictured here wearing a menagerie of denim outfits, the boy band NSYNC should’ve thought twice before leaving the house as they did.

From Justin’s bandana to Chris’s denim vest, there’s very little right about this picture. Let’s hope the boys of NSYNC learned from their obvious fashion disaster mistakes and banished these outfits forever!

Pictured at the 2003 Spirit Awards, Brad and Jen looked stylish yet casual as they walked the red carpet. While Jen is a breath of fresh air in her sleek black outfit, we have to wonder what made Brad wear that shirt. It looks like something his grandmother had embroidered for him.

Once the most glamorous couple of the early 2000s, they regularly made headlines for their alluring looks and incredible style. While Jen looks gorgeous, we’ll forgive Brad for this little blunder, as he usually looks perfect.

We have no words that accurately describe the outfit Mya wore to the KTU Miracle on 34th Street Show in 2001. Wearing a blue velvet patchwork skirt, the singer thought it a great idea to pair it with metallic boots, an oversized black jacket, and a crop top.

While we think that blue is her color, perhaps less of a clash in fabrics or a different look altogether would be more fitting or appropriate. Good try, though, Mya! You look good regardless of what you’re wearing!

Hot off her American Idol win, Kelly Clarkson attended the 2005 premiere of Swimfan wearing clunky heels, a pair of bootleg jeans, and a strapless dress. While we like the dress, the outfit would’ve looked far better sans jeans.

Kelly has come a long way and improved her style over the years, so we’ll forgive her for this small mistake once she started gaining fame and popularity. You’re gorgeous, Kelly, so we’ll overlook your earlier fashion blunders.

Black Eyed Peas singer Fergie put her worst fashion foot forward and rocked up to an event in 2005 looking like she was going to play football in heels. With cropped pants, a cami, and a cropped sweater, Fergie decided heels would top off this already bizarre outfit.

Fergie is known for her eccentric outfits, but this one is the most bizarre yet. Maybe a different pair of shoes, pants, cami, or sweater would improve this look, but somehow we doubt it.

Desperate Housewives star Eva Longoria channeled her inner Pocahontas as she donned this leather ensemble at the 2001 Lara Croft: Tomb Raider premiere. With nothing but tape keeping her jacket “closed,” we’re sure the paparazzi were on high alert to snap that perfectly timed pic if the wind blew even just a little.

While this outfit might not be the best thing she could’ve worn, Eva certainly rocked it and looked amazing as she walked the red carpet that year. You’d be hard-pressed to find a picture of this bombshell ever looking anything but glamorous.

Diva Mariah Carey shocked fans with a skintight pair of jeans and a barely-there butterfly top ensemble at the VH1 Divas Concert in 2000. Known for her stunning voice, the singer opted for a more casual look for this glamorous event. And boy was she turning heads as she walked the red carpet!

Mariah Carey is synonymous with over-the-top glamor, so why wear jeans rather than a fancy dress or ballgown to this glamorous affair that celebrated female singers? We don’t know!

So who’s going to tell Mandy Moore that long denim skirts went out of style in the ’80s? Walking the red carpet for the 2000 launch of her new album I Wanna Be With You in New York, the singer looked odd as she paired a glam top and heels with a basic skirt.

We’d have paired this cute, feathery top with a pair of skintight black jeans, but perhaps the skirt was a nod at the singer’s squeaky clean image that she portrayed for so many years with her bubblegum pop music. We guess we’ll never know…

Does everyone on the planet own an “I Heart NY” t-shirt, and is it appropriate to wear it to any event? Photographed at the 2001 premiere of the hit movie Save the Last Dance, Kerry Washington arrived wearing a blazer, a beautifully cut skirt, and a rather plain t-shirt.

We love this funky look, albeit it’s a bit casual. But somehow, Kerry makes it work and only appears on our list of 2000s red carpet fails due to this more casual look from an actress who’s usually polished and in full glam.

We can’t fathom what Gwyneth Paltrow was thinking when she arrived at the 2005 premiere of The Next Best Thing wearing this pink and beige outfit. While the jacket or pants would’ve worked independently, the colors don’t go together, leaving her looking like a milkshake.

Now the CEO of her fashion and wellness empire, Goop, Gwyneth has come a long way from this cringeworthy look that made it onto our list of red-carpet fails of the 2000s. Don’t worry, Gwyneth, we’ll pretend this never happened.

Former Baywatch babe Carmen Electra stepped out on the red carpet at the Maxim Hotel opening in Los Angeles in 2000 wearing this patchwork monstrosity. While leather is a great fabric for an edgy look, patchwork leather has the opposite effect.

We can only ponder why Ms. Electra chose patchwork and leather for the opening of a hot hotel. Whatever it was, she landed up on the list of red-carpet fails that year. Maybe try a different textile next time, Carmen.

Who can forget Björk’s swan dress from the 2001 Academy Awards? Turning more than a few heads, the eccentric singer donned the rather odd design by Marjan Pejoski, earning herself the label of having a red-carpet fail in 2001.

While we can certainly appreciate a designer’s work, we can’t help but wonder what the inspiration for this specific piece was. But, if anything, it got people talking about Björk and her dress, which is always good.

Eve’s outfit for the 2008 MTV Movie Awards is one of the best on this list of red carpet fails, as it featured a striped poncho paired with some cute cropped jeans. Bringing the outfit together with a matching bag and shoes, Eve looks pretty well put together.

Perhaps it was the fact that the outfit was too casual for the event that got fashion critics talking. As far as we can tell, there’s nothing glaringly wrong with this cute, summery outfit that makes her look laid-back and relaxed.

Brittany Snow looked ready for lunch with grandma when she walked the red carpet at an NBC event back in 2005. Combining a white dress with a black shrug and black heels, the actress looks far too timid in an outfit that’d be more suited for an older woman.

Brittany is young, and we strongly feel she could’ve jazzed up the outfit by ditching the cardi and swapping the pointy-toed heels for a sparkly open-toe. As much as we love Brittany, we can’t forgive her for this red-carpet failure.

It must’ve been a chilly night for Mary J. Blige to wear a thick fur coat to the 2001 Billboard Music Awards. While we can’t see any snow on the ground, it must be there, because why else would she wear this big fashion faux pas and risk the folks from Peta showing up to douse her in paint?

Her outfit leaves us scratching our heads as we try to figure out how many looks she combined to get this overall look that combines a candy cane and a gangster. We count at least three. How many do you see?

This, folks, is why our parents tell us never to run with scissors. Someone should’ve told Tara Reid this before she walked the red carpet at the 2002 Billboard Music awards looking like she tripped and cut her skirt.

Once a fashionista with a bevy of fans, the actress has clearly made some bad choices in her life, and this outfit is one of them. Listen to your parents next time, Tara, because they could’ve saved you the embarrassment of becoming a red-carpet fail.

Kim K certainly loves her boots as she appears on our list for the second time wearing the same white boots as before. It could be that both pictures were taken at events in 2006. That doesn’t excuse this rather poor fashion choice, though.

Kim has, thankfully, updated her wardrobe since then. She recently added being a designer to her already impressive list of accomplishments on her resume with the launch of her new Skims range. Good on you for ditching the boots and putting your best fashion foot forward, Kim! We’d hate to see another red-carpet fail list that includes her.

Did Jennifer Love Hewitt wear her grandmother’s white crocheted tablecloth to the 2002 premiere of Spider-Man in LA, or are we just seeing things? We know it’s a poncho, but it’s too close to a tablecloth to be ignored.

Pairing her oversized poncho with bootleg jeans and boho jewelry, Jennifer looks casual and relaxed… Maybe a little too relaxed for our liking. All she needed was a flower painted on her face and her hair left loose to look like a hippie at a Woodstock revival show.

Why, oh, Why, Julia? Wearing a floral dress with a thin, possibly knitted shawl, Julia Stiles became a red carpet fail. She wore this less-than-impressive outfit to the 2002 premiere of her movie Secretary.

We get that she was going for that demure, almost innocent look that was a strong theme in the movie. Sadly, we can’t help but think there were so many easier ways to achieve this. Even a pencil skirt and a classic white button-up shirt would’ve been better than this old-fashioned nightmare.

Was it summer or winter when Lindsay Lohan attended the Neil Bogart Memorial Concert in 2002? While her tracksuit and skinny scarf scream winter, she also wore black flip-flops which made it feel like summer.

Thanks for confusing us, Lindsay! And just so you know, a tracksuit is far from appropriate to honor one of the legends of the music world. Maybe dress up a bit more next time, because this outfit is not it.

We don’t know where to start when looking at this interesting/eccentric/downright weird outfit that Pink wore to the 2000 MTV Video Music Awards. While we know that this fun singer likes to stand out, we can’t imagine what made her choose this!

The top, the jeans, the coat, the hair! It’s so hard to come up with anything nice to say about this outfit. But if we had to choose anything, we can say that we like the shade of her hair color. Everything else is just too much.

JLo made a surprisingly well-received entry into the world of acting. With movies like Enough on her now-impressive list of feature films, her outfits leave much to be desired. Only JLo could pull off this frilly dress and coat combo that resembles a Sunday afternoon with grandma outfit.

Stepping out onto the glitzy red carpet for the 2002 premiere of her new movie, the singer/actress looked more like a lady who lunches than the booty-kicking baddie she played in the movie. Hire a better stylist, Jen, because whoever dressed you for this event did you dirty!

It was clear that Jessica Simpson liked the color red as she wore this interesting all-red leather outfit to the 2001 American Music Awards. She looked rather interesting, even if she did resemble a bright-red tomato ripe for the picking.

Jessica is most famously known for her reality show documenting her journey as a newlywed when she married former 98 Degrees singer Nick Lachey. While the marriage didn’t last that long, this outfit will forever be remembered as one of her worst.

Reese Witherspoon was a hot commodity after her appearance in Cruel Intentions. It’s no surprise that she attended many red-carpet events, such as this one for the Blockbuster Entertainment Awards in 2000. But, it wasn’t her popularity that turned heads at this event. Rather, it was this shapeless blue dress.

Resembling a metallic shopping bag, the dress had little detail and did nothing to make the young actress stand out. We will, however, applaud her for at least matching her shoes to the dress, making it a solid choice for a red carpet fail.

Ashton Kutcher and Brittany Murphy starred in one of the funniest movies, making it normal to see them at events together. But, as is clear from this photo snapped at the 2002 VH1 Awards, their outfit choices were anything but in sync.

While Murphy opted for a pale pink ensemble that made her look sweet, Ashton donned a vest. He paired it with his fresh-out-of-bed hairstyle, leaving him looking like he had put in no effort. We expected more effort from Ashton Kutcher!

It seems like Janet Jackson suffered a bit of a snag as she walked the red carpet at the Vanity Fair Oscars Party in 2002 wearing a top that left little to the imagination. Did her knitted sweater get snagged on the car door and fray, or was this an actual choice?

To make matters worse, the singer paired her barely-there top with a long, oversized jacket. This left many people scratching their heads and wondering just what she was trying to achieve with this rather odd ensemble. Whatever it was, the turned heads and odd looks didn’t bother the singer as she smiled broadly for the cameras.

Gwen Stefani is in a league of her own regarding fashion. This is just the type of outfit that the former No Doubt singer was known for as she walked the red carpet at 2001’s My VH1 Music Awards.

Pairing her houndstooth pants with a tight bodysuit, the singer turned heads. She made her way around the event, wearing her signature red lip and sharing a smile with those around her. Though it may not be everyone’s cup of tea, Gwen has fun getting dressed… Even when the majority of her wardrobe has her looking like she’s committed a red-carpet fail.

Ms. Aguilera makes it onto our list for the second time. This time photographed at an event in 2001, Christina mixed leather and denim to come up with this, um, unique look. While we all love a good pair of denim, we don’t know how to feel about these.

Christina went through a paper-boy hat phase, too, so while the hat is no surprise, it does nothing for her outfit and should’ve been left at home where it clearly belonged. Thank goodness she saw the error of her ways and is rocking a more glamorous look of late – a far cry from her wild fashion sense from the early 2000s.

No one, and we mean no one, will ever be able to get this extreme fashion blunder out of their heads. While it’s been over 20 years since Britney and Justin wore full denim outfits to the 2001 American Music Awards, the look lives on in our nightmares.

From Justin’s denim cowboy hat to Britney’s matching bag, there’s not enough time or words to list every single thing wrong with this outfit choice of one of the most famous couples from the 2000s. Better luck next time!

Rihanna makes it onto our list for the second time with another appearance at a red carpet event in 2005. This time wearing pants with a vest and Converse sneakers, the singer looked like she was on her way to a basketball game rather than a Hollywood event.

While we will admit that she looks rather cute and innocent, the outfit could do with a bit of glamming up and is far better than her outfit from our previous entry on this list of the worst 2000s red carpet fails.