What were they thinking?! Super low cut jeans, UGG boots, belly shirts and butterfly hair clips oh my! Check out the most memorable and cringeworthy fashion moments of the early 2000’s. Click the NEXT button to start slideshow.

Paris Hilton

Reality star and socialite Paris Hilton definitely had a signature look going on a decade ago which included a great spray tan, a tiara and anything that showed off her flat tummy.

Christina Aguilera

Not only were Christina Aguilera’s vocals a head-turner, so were her fashion choices in the 2000’s.

Nicole Richie

Before becoming a fashionista in her own right, Nicole Richie’s fashion game went through a rough patch.

Britney Spears

Pop princess Britney Spears was on top of the world in her career, but taking a look at some of her fashion choices has us scratching our head. Who could forget the iconic denim dress!

Jessica Simpson

Pop star turned fashion designer Jessica Simpson made some fashion mistakes in her earlier years, red latex anyone?

Pink

Back when Pink’s hair was actually “pink,” she loved to complement her rebellious attitude with her rocker style.

Jennifer Lopez

Who could forget the moment Jennifer Lopez walked the red carpet at the Grammy’s in the now infamous green Versace dress!

Lindsay Lohan

This good girl, gone bad was in her film heyday in early 2000’s.

Kelly Clarkson

The first winner of American Idol Kelly Clarkson fell victim to some of the major fashion fails of the 2000’s including belly shirts and flare jeans.

Gwen Stefani

Singer Gwen Stefani definitely marched to the beat of her own drum when it came to her unique fashion choices.

Ryan Seacrest

Ryan Seacrest embraced the uber-popular hair trend, frosted tips!

Velour Jumpsuit

Juicy Couture was literally everywhere and worn by almost every celeb during the early 2000’s.

The Trucker Hat

With celebrities such as Ashton Kutcher and Justin Timberlake embracing the truck hat trend, you began to see it everywhere!

Low-Rise Lace Up Pants

These super low-cut pants with lace tie-ups were a huge trend in the 2000’s, worn by almost every performer during that era.

The Fedora

From trucker hats to fedoras, hats were a huge trend in the 2000’s.

Cropped Pirate Pants

From Queen Bey to Gwen Stefani, multiple celebs were guilty of sporting the cropped pirate pant trend.

Red Leather

Leather was a major trend in the 2000’s. Why red was the go-to color, we’ll never know.

The Handkerchief Hemline Dress

The handkerchief hemline dress made appearances on numerous red carpets throughout the 2000 decade.

Slip Dress

Celebrities began embracing undergarments as fashion staples. Behold, the slip dress trend.

The Pashmina

The pashmina was one of the most worn fashion accessories on the red carpet in the 2000’s.

Cargo Pants

Although the comfort factor was in full effect, the cargo pant trend was a major eye sore.

Tara Reid

In 1999, American Pie hit the big screen, sky rocketing Tara Reid’s career in the early 2000’s.

Kim Kardashian

Reality star and makeup guru Kim Kardashian has seriously upgraded her fashion game in the last decade!

Eve

Eve was on top of her music career in the 2000’s, unfortunately we can’t say the same for her fashion choices! She’s come along way since her Ruff Ryder days.

Beyonce

Remember when Beyonce and her Destiny Child group members would all dress in matching outfits?!

Destiny’s Child

The matching continues!

Destiny’s Child

And continues…..

Scarlett Johansson

Before she became “Black Widow” as part of the mega movie franchise The Avengers, Scarlett Johansson made a few style mistakes.

Sarah Michelle Gellar

With the popular series Buffy the Vampire Slayer and films like Cruel Intentions, Sarah Michelle Gellar made a number of red carpet appearances in the early 2000’s.

Hilary Duff

Former Disney darling Hilary Duff has come a long way since her Lizzie Maguire days!

Reese Witherspoon

Reese Witherspoon was one of many actresses who embraced the hair clip trend of that era.

Sarah Jessica Parker

The usual fashion-forward Sex in the City star Sarah Jessica Parker made a few fashion hiccups in the early 2000’s.

Jessica Biel

Child actress turned movie star Jessica Biel quickly gained a more polished look as she and her fame grew. Check out those tan lines!

Justin Timberlake

Speaking of Jessica Biel, here’s her other half Justin Timberlake, who went through a few fashion phases in the 2000’s.

N’SYNC

Justin Timberlake, along with his bandmates of N’SYNC had more than a dozen WTF fashion moments.

Ashley Tisdale

Former Disney star Ashley Tisdale went for the layered look and piled on the accessories for her premieres.

N’SYNC

I’m just going to leave this one right here….

Mya

Mya was one of the biggest recording arts in the 2000’s with her collaboration on Lady Marmalade topping the charts.

Lil’ Kim

Also, a collaborator on Lady Marmalade, rapper Lil’ Kim wore some unforgettable cringe-worthy outfits.

Ashlee Simpson

Trying her way in the music game, singer Ashlee Simpson tried a few different looks, and hair colors, before settling on her style.

Alicia Keys

Alicia Keys had a few “what was she thinking” moments during her rise in fame. Her hit song “Fallin'” debuted in 2001.

Mischa Barton

With the popularity of the hit series The O.C., came numerous red carpets for lead actress Mischa Barton.

Blake Lively

This now fashion maven didn’t always have her style together.

Rihanna

Singer Rihanna has her own unique sense of style, and soon found her way, but not until after a few styling fails along the way including belly chains and showing her underwear.

Kristin Cavallari

With the hit reality series Laguna Beach debuting in the early 2000’s, came an onset of California girls and fashion. You decide if it was a hit or miss.

Lauren Conrad

The reality front woman of Laguna Beach is now a fashion designer and television personality.

Mary-Kate and Ashley Olsen

It was tough for the Olsen twins to escape the limelight during the 90’s and 2000’s with their popularity with television shows, movies and clothing line.

Mandy Moore

Portrayed as the girl next door, Mandy Moore has some choice fashion moments in the early 2000s. Bring on the plaid and fringe!

Fergie

During the era of the micro-mini skirts and belly shirts, singer Fergie pulled off this look time and time again.

Avril Lavigne

Grab an oversized tie and a pair of chucks if you want to dress like singer Avril Lavigne in the early 2000’s.

Backstreet Boys

Maybe they were planning on going skydiving after the show? Seriously, what’s the reason behind the goggles?

Eva Longoria

Let’s take a trip down Wisteria Lane. This former Desperate Housewives star loved a great crop top, or sometimes no top, when she appeared for events.

Rachel Bilson

Actress Rachel Bilson has seriously stepped up her fashion since her days on The O.C.

Anne Hathaway

Prior to becoming a Hollywood A-lister, Anne Hathaway made some style slip-ups.

The Spice Girls

Leather, leather, and more leather. In 2000, 4 of the 5 Spice Girls reunited to make their 3rd and final album entitled “Forever.”

Natalie Portman

Actress Natalie Portman was already a Hollywood veteran by the time she hit the early 2000’s, first hitting the big screen in 1994 at the age of 11 in the movie The Professional.

Cameron Diaz

Even Cameron Diaz was guilty of making some fashion flops.

Lara Flynn Boyle

Who could forget Lara Flynn Boyle’s ensemble worn during the 2003 Golden Globe Awards.

Björk

A look back to singer Björk’s infamous swan dress for the 2001 Oscar’s red carpet. What was she thinking?