Over 30 Celebrities Who Look Completely Different in Their Photos from the 2000s

Written by: Abdullah
Published:

We thought cherry logos and fuzzy dice were a thing of the past. To celebrate the return of the nineties, let’s take a look at some celebrities who have since changed their style.

Kim Kardashian

Fashion was so bad in the nineties that pretty much everyone looks better today than they did back then. At that time, Kim Kardashian wasnโ€™t wearing Skims but Juicy. In this photo, we see Kimmy in a pink velour Juicy Couture tracksuit, flip-flops, and a white Louis Vuitton handbag. And most notably, her makeup is very different from what it is now.

(Izquierda) Instagram // @millenialarchives | (Derecha) Reddit // u/acid_woo

Ashley Olsen

To be honest, weโ€™re completely obsessed with the Olsen twins. Maybe it’s because they were everywhere in the 90s, and in the 90s, they became the queens of fashion. When the twins started to express their personal style, Ashley was the more classic of the two.

(Left) POPSUGAR // Evan Agostini | (Right) Pinterest // @WhoWhatWear

The twins have retired from acting (who can blame them?), but they remain active in the fashion world. Ashley now has a more grown-up version of her grunge look.”

Ariana Grande

“The twins have retired from acting (who can blame them?), but they remain active in the fashion world. Ashley now has a more grown-up version of her grunge look.”

(Left) Twitter // @firelrd_zuko | (Right) Twitter // @Vilulodoruggi

Ariana Grande has come a long way in terms of style. Now, she often sports a high ponytail along with glamorous dresses and oversized streetwear.”

Mischa Barton

“Here is a true celebrity from the nineties. In fact, actress Mischa Barton was literally named the It girl of 2003. With her role as Marissa Cooper, she was who we all wanted to be. However, since then, she has spoken about the pressure and paparazzi intrusion during that time.

(Left) Pinterest // @buzzfeed | (Right) Reddit // u/PrincessBananas85

In this snapshot from the orange carpet of the nineties, Mischa wears a long gray sequined and pleated top, jeans, and shoes.”

Lindsay Lohan

“Continuing with the nineties It girls, we arrive at Lindsay Lohan. The path of this star is rather tragic. She was a huge child star, found success in the nineties with major teen movies, and then became a sensationalized tabloid spectacle. Like Mischa, Lindsay was hounded by the press, with her every move scrutinized.

(Left) Pinterest // @buzzfeed | (Right) Facebook // Lindsay Lohan”

Naturally a redhead, Lindsay sported some less-than-flattering looks in the nineties. Remember when she went blonde? Now she’s back to her natural red.”

Rihanna

“The good girl gone bad has also had a major style transformation. RiRi is considered one of the style queens: sheโ€™s bold, experimental, and a trendsetter. In the nineties, she was a fresh-faced pop star wearing baby doll tops and cowboy boots.”

(Izquierda) Pinterest // @buzzfeed | (Derecha) Pinterest // @twitter

“Now she’s a true fashion powerhouse with her own brand. Here, the singer and makeup mogul is wearing an oversized striped blazer with a cap and gold chains.”

Gwen Stefani

Some might say that Gwen Stefani has maintained her style over the years. After all, sheโ€™s always worn platinum blonde hair and red lipstick (despite this photo). However, while she hasnโ€™t aged much, Gwen has evolved with the times when it comes to style. Plus, her love life has had a certain sartorial influence.

(Left) Reddit // u/Chef__Goldblum | (Right) HawtCelebs // hawtcelebs.com

In the nineties, Gwen launched her solo album and embraced a skater style. Now, thanks to her fiancรฉ Blake Shelton, she leans more toward country. Just look at those boots.

Tara Reid

Actress Tara Reid is one of those stars who seems to be stuck in the nineties. Back then, she was a star, but tabloids painted her as the ultimate party girl. After a botched plastic surgery, the star has mostly flown under the radar.

(Left) Reddit // u/giinkgoo | (Right) Daily Mail // The Daily Stardust

In this photo, Tara is wearing an array of nineties items. Weโ€™ve got low-rise jeans, dog tags, a sideways trucker hat, a belly chain, and a truly awful layered top. She definitely looks different today.

Katy Perry

In the mid-nineties, Katy Perry burst onto the scene with her hit โ€œI Kissed a Girl.โ€ Before that, she tried to make it as a gospel singer under the name Katy Hudson. Despite her Pentecostal pastor parents’ opinions, she became a massive pop star.

(Left) Reddit // [deleted] | (Right) Instagram // @thombrowne

Back then, Katyโ€™s style was pretty low-key compared to her later looks. No cupcakes or burgers, just yellow stiletto heels, shorts, and a top. Now sheโ€™s a true fashion chameleon.

Paris Hilton

Sheโ€™s the queen of the nineties! Paris Hilton appeared out of nowhere and was suddenly everywhere. With her Juicy tracksuits and tiny dogs, Paris was the It girl of the decade. We donโ€™t care what others say.

(Left) Instagram // @parishilton | (Right) Instagram // @popsugar

Though Paris Hilton no longer has her baby voice, her style is quite similar. Of course, she fully leans into her persona, embodying all things Paris. And her hair and…

Christina Aguilera

Surely, every kid in the nineties wanted to look like Christina Aguilera after her makeover with โ€œDirrty.โ€ In the 90s, she was a Disney kid turned pop star, like Britney. However, with her new album, Christina became Xtina, debuting wild beauty looks and a love for chaps.

(Left) Pinterest // @buzzfeed | (Right) Instagram // @xtina

Over the years, Christina Aguilera has gone through several style transformations. For instance, she had that burlesque phase after starring in the movie. Now, she looks like the multimillion-dollar star she is.

Avril Lavigne

When we first met Canadian teenager Avril Lavigne, she was presented as the ultimate skater girl. Avril was the rebel of the era. Or at least, thatโ€™s what we were supposed to think.

(Left) Twitter // @2000sthetic | (Right) Facebook // Avril Lavigne Fans

Avril has stayed true to her punk rock vibe over the years, with a few updates. For a while, she leaned into kawaii styles, although she faced some criticism for it. In this shot, sheโ€™s wearing punk pink plaid but with a more modern silhouette.

Britney Spears

Oh, Britney, Britney, Britney. The Princess of Pop was an absolutely huge star in the nineties, with hit after hit. Like other young stars of her generation, Brit was followed, harassed, and scrutinized by the paparazzi. All this led her to suffer a breakdown.

(Left) Pinterest // @kitschygoth | (Right) Facebook // Digi24

Itโ€™s been a while since Britney has looked her best because she was trapped in an abusive conservatorship. She stated that she wasnโ€™t allowed to get her hair or nails done. Now that her father has been removed, weโ€™re seeing more of her carefree style.

Kelly Osbourne

Like Avril Lavigne, Kelly Osbourne had a more rebellious style than other stars of the nineties. As the daughter of rocker Ozzy Osbourne, she grew up with a metallic edge and an attitude to match. Kellyโ€™s outfits during this decade were quite emo: here she wears a bow in her hair with a Care Bears tutu dress.

(Left) Reddit // u/Chef__Goldblum | (Right) Reddit // u/Bo-naana

Fans were pretty surprised when Kelly Osbourne revealed her new look in 2021. Besides losing weight, it seemed the star had undergone some major cosmetic surgery.

Courtney Love

During her twenties, Courtney Love released solo music and acted in several films. She also wrote three manga collections. In the previous decade, she was known as a grunge musician and the wife of Nirvanaโ€™s frontman, Kurt Cobain.

(Left) Pinterest // @thecut | (Right) InStyle // Dave Berett

Weโ€™re quite surprised to see that the wild Courtney Love has transformed into a rather polished lady. Of course, sheโ€™s still a rock star at heart.

Khloรฉ Kardashian

All the Kardashian-Jenner sisters look very different from when they first appeared on our TV screens. The youngest Kardashian, Khloรฉ, has always considered herself the โ€œfatโ€ sister. With her two petite older sisters, itโ€™s no surprise that Khloรฉ, being taller, always felt like she stood out.

(Left) Pinterest // @usweekly | (Right) Pinterest // @margaagrma93

After several โ€œrevenge bodies,โ€ Khloรฉ is now unrecognizable. She has definitely had cosmetic surgery on her face and probably on her famous body too. Plus, her style game has improved.

Drew Barrymore

As a child star, Drew Barrymore has been around long before the nineties. However, when she joined the cast of the Charlieโ€™s Angels reboot, she became a standout girl of the nineties.

(Left) Pinterest // @emilyna | (Right) Facebook // Drew Barrymore, New York

Seriously, even Destinyโ€™s Child referenced that movie and called out the angels by name. Imagine that. Here, a laid-back Drew is wearing bootcut jeans, a khaki bomber jacket, and a slogan tee. Her hair is highlighted blonde and pulled back in a ponytail. Since then, Drew has leveled up.

Beyoncรฉ

Speaking of Destinyโ€™s Child, how could we not talk about Beyoncรฉ? Obviously, sheโ€™s been an icon since birth, but she too was subject to nineties trends. As a girl group member, Beyoncรฉ wore especially shiny and strangely shaped outfits.

(Left) Instagram // @carterfamily_beyonce | (Right) Twitter // @housewivesofslc

Here, sheโ€™s wearing two pieces of fabric held together by ruched strings. Beyoncรฉ clearly still enjoys a bit of sparkle, but her style is much more high-fashion now. The star often wears stunning haute couture looks.

Ashley Tisdale

Honestly, Ashley Tisdale wore some of the most outrageous outfits of the nineties. To be fair, she was a teenager with newfound fame, expected to appear at events looking chic. Did nobody get her a stylist? Did anyone have a stylist in the nineties?

(Left) Instagram // @boshbabexoxo | (Right) Facebook // J-14 Magazine

In this wild outfit, the actress wears a long slip dress with ruffles over a T-shirt and straight-leg jeans. Accessories included a beanie and a sequin handbag. Thankfully, sheโ€™s left this look in the past.

Gabrielle Union

Actress Gabrielle Union has starred in many teen movies. Her most iconic role, however, was as the cheer captain in Bring it On from the year 2000. This is literally one of our favorite movies of all timeโ€”go Clovers!

(Left) Facebook // Gabrielle Union | (Right) Instagram // @larryjarahsims

Gabrielle Union looks great in the nineties, but she also fell into the eraโ€™s trends. Did anyone look good in these styles? Here, sheโ€™s wearing a high-neck sequin top with blinding white jeans. Yikes. Thankfully, the star now rocks a much chicer 2021 look.

Nicole Richie

If Paris Hilton was the queen of the nineties, her best friend Nicole Richie was undoubtedly the princess. While Paris always dressed in pink and diamonds, Nicole was the grungier one of the pair. Often sporting bandanas and hats over her messy hair, Nicole looked like a true wild child of the nineties.

(Left) Pinterest // @90scanadalover | (Right) Pinterest // @dailymail

Since then, Richie has become much more polished. She even founded her own fashion brand and now looks incredibly stylish. We especially love this blue ponytail.

Hilary Duff

As a Disney Channel star, Hilary Duff wore many of the same terrible fashions as her peers. Here we can see a floral rosette with chains hanging over a pair of low-rise combats. Seriously, will we ever get over this fashion crime? This outfit also includes a small 90s handbag (which is back in style) and a striped tank top.

(Left) Reddit // u/GillyGooze | (Right) Pinterest // @twitter

What was this decade? Now, Hilary dresses much more polished. In the photo on the right, sheโ€™s sporting chic round sunglasses with an oversized trench coat.

Mary-Kate Olsen

Weโ€™ve already talked about Ashley Olsen, and now itโ€™s Mary-Kateโ€™s turn. Of the two, MK has always had the more grunge and bohemian style. Honestly, we love it. In fact, if anyone pulled off the style of this decade, it was the Olsen twins.

(Left) Pinterest // @baird1351 | (Right) Twitter // @VersaceVenus_

Along with her sister, Mary-Kate founded a fashion brand called The Row. The sisters still dress in a goth-grunge style but with chic and high-fashion touches. Ah, the Olsen twinsโ€”theyโ€™ve given us so much.

Jennifer Lopez

Okay, we know this photo of Jennifer Lopez is from the โ€œAll I Haveโ€ music video with LL Cool J. But, just look at her! She was still in her โ€œJenny From the Blockโ€ phase and was rarely seen without a big pair of hoops.

(Left) Reddit // u/hilda123459 | (Right) Pinterest // @iodonna

Weโ€™re obsessed with this baby pink long coat paired with pigtails. In the nineties, J.Lo wore all kinds of crop tops, bandanas, and tracksuits. In the selfie on the right, she looks much more modern. However, sheโ€™s still a fan of crop tops.

Demi Lovato

Just look at Demi Lovato! The star was on kidsโ€™ TV in the early nineties and then found fame starring alongside the Jonas Brothers in Camp Rock. In this shot, we can see some nineties fashion staples: first, platform peep-toes and a strapless silver party dress.

(Left) Pinterest // @garotasfashion | (Right) Twitter // @PopCrave

Since the nineties, Demi Lovato has come out as non-binary. Their style is more adventurous than beforeโ€”even sporting a mullet! Weโ€™re definitely here for it.

Miley Cyrus

From child star to child star, Miley Cyrus has changed a lot since the nineties. Back then, the singer was a Disney star with a hit TV show and lots of catchy, cheesy songs. In this photo, a young Miley is seen wearing a sheer top with blonde highlights.

(Left) Pinterest // @womenabout55 | (Right) ELLE // Robert Kamau

Miley has gone through many styles since the nineties. Currently, sheโ€™s embracing rock music and a style filled with jewelry, tattoos, and even a mullet.

Selena Gomez

Selena Gomez also acted as a child, appearing on the same show as Demi Lovato. Later, she became better known on Disney Channel and eventually transitioned to pop music. In this early red carpet photo, a young Selena wears Converse sneakers and a vest.

(Left) Pinterest // @womenabout55 | (Right) ELLE // Robert Kamau

A vest, people! Luckily, Selena hired a stylist at some point in her career. In the photo on the right, sheโ€™s wearing a bright pink jumpsuit adorned with sequined catsโ€”simply incredible. Bold!

Anne Hathaway

Sheโ€™s now a major movie star, but Anne Hathaway was also a dorky teen in the nineties. Just look at the โ€œbeforeโ€ photo to see it. In fact, look at any photo of Anne from this period. Here sheโ€™s posing in bootcut jeans, a halter top, and a rather ugly denim bag.

(Left) Twitter // @AnneHathabae | (Right) Instagram // @annehathaway

Nowadays, itโ€™s nearly impossible to see Anne Hathaway looking anything less than perfect. She shines, wears elegant suits, and continues to reign as an acting icon.

Ashlee Simpson

Where could we even start with this outfit? Seriously, how did this look ever see the light of day? From what we can see here, Ashlee Simpson is wearing a long tutu skirt, high-top baseball (or bowling?) shoes, a sheer shirt over a T-shirt, and a low-slung belt.

(Left) Twitter // @keatonkildebell | (Right) Pinterest // @fashionistacom

Why didnโ€™t anyone tell her to take off at least one of these fashion abominations? Like the others on this list, Ashlee Simpson has since matured. Or at least she hired a stylist.

Mandy Moore

Mandy Moore and Anne Hathaway recently shared a throwback photo of themselves decked out in nineties outfits. Thankfully, theyโ€™ve realized just how awful those outfits were. Here, a young Mandy is rocking quite the combination.

(Left) Reddit // u/almondbutterpecan | (Right) Instagram // @mandymooremm

Her plaid skirt is lime green and purple, paired with a sparkly pink turtleneck top. Mandy Moore wore a lot of pink in the nineties. She still likes bold colors, but now theyโ€™re less bubblegum and more refined.

Amanda Bynes

We have another sad story with Amanda Bynes. The star found success with her sketch comedy on Nickelodeon and eventually got her own show. She then starred in many hit teen movies. However, she also suffered intense media scrutiny, which led to struggles with substance abuse.

(Left) Pinterest // @nymag | (Right) Twitter // @merissahansen17

In the nineties, Amanda Bynes looked stunning. Here, sheโ€™s wearing dark blue studded jeans, a tank top, and straightened hair. Now, she sports a slightly more dramatic look.

Taylor Swift

How adorable is she! Early in her career, Taylor Swift was a curly-haired country star often seen in cowboy boots. As her career progressed, Swift developed a more polished style, continuing to evolve with each album.

(Left) Pinterest // @perksofabear | (Right) Instagram // @tswizzle_tay

In this first image, Taylor is rocking nineties nude lips along with fringed moccasin boots. Remember those? Now she sports coordinated outfits with high-fashion pieces. Look at those shoes!

Cameron Diaz

Weโ€™ve already mentioned one nineties angel, and thereโ€™s room for one more. Like Drew Barrymore (her best friend), Cameron Diaz began working long before the nineties. During this period, she wore her signature straight blonde hair along with decade trends. Here we have a strapless top with a long layered necklace. Chills.

(Left) Vogue // Jeff Kravitz | (Right) Reddit // u/FeederTheSuperhero

Cameron Diaz has retired from acting, so we donโ€™t see her as often anymore. Her style is quite down-to-earth, with simple jewelry and her classic blonde locks.

Victoria Beckham

Former Spice Girl Victoria Beckham sported some truly questionable outfits in the nineties. In fact, the โ€œWAGโ€ (wives and girlfriends) fashion trend took off because she, Cheryl Cole, and other celebs dressed up for the 2006 World Cup.

(Left) Twitter // @pray4mischa | (Right) Twitter // @victoriabeckham

Here we can see one of VBโ€™s looks from that era. Check out that animal print! Since then, she has founded a successful fashion brand and joined the ranks of the stylish elite. Who wouldโ€™ve guessed?

Written by Abdullah

Abdullah Malik is an SEO writer and content reviewer specializing in entertainment and celebrity news with TrendingThat.com. He has written over 2000+ articles and has helped rank numerous websites. An avid follower of media, music, TV, and film, Abdullah combines his passion for entertainment with his expertise in SEO to create engaging, high-ranking content. As a dedicated writer and content reviewer, he is always looking to enhance his skills as a storyteller, journalist, and SEO expert.