Celebrity Style Stars: Then and Now

From Kim Kardashian to Ryan Reynolds, look back at the stars' questionable fashion choices -- and how they've transformed!

They're some of the most stylish stars in Hollywood today -- but these celebrities weren't always so fashionable. From Justin Timberlake to Sandra Bullock, see how their red-carpet looks have evolved (and improved!) over the years.

Sofia Vergara

Sofia Vergara fashion

SGranitz/WireImage; Jason Merritt/WireImage

There’s nothing Modern about Sofia Vergara’s old-school style! While the actress’ toned tummy and gorgeous locks haven’t changed, we’re happy to see she’s ditched the bedazzled capris (like the ones she wore to the American Comedy Awards in February of 2000) in favor of sexy, curve-hugging gowns.

Jennifer Aniston

Jennifer Aniston fashion

Terry McGinnis/WireImage; Jon Kopaloff/FilmMagic

In 1995, Jennifer Aniston’s haircut was the envy of women everywhere. But her fashion sense? Not so much. Fortunately, the actress has changed that, trading in sheer sweaters for refined ensembles, including the sleek peplum dress she showed off at the premiere of Wanderlust in February of 2012. We’re sure fiancé Justin Theroux would approve!

Justin Timberlake

Justin Timberlake fashion

Jeff Kravitz/FilmMagic; Steve Granitz/WireImage

From bleach blonde curls to baggy clothes, Justin Timberlake and his fellow 'NSYNC members were the picture of awkward '90s fashion. But if you can’t tell by the title of his latest single, this suave solo artist now loves stepping out in a suit and tie, much like the gray ensemble he rocked at this year’s Screen Actors Guild Awards on Jan. 27.

Emma Stone

Emma Stone fashion

Vince Bucci/Getty Images; Dave M. Benett/Getty Images

She’s one of Hollywood’s most fashion-forward celebs, but judging by her dainty blue mini at the premiere of Superbad in 2007, Emma Stone wasn’t always that way. But after going blonde and traveling the world to promote The Amazing Spider-Man last summer, Stone emerged a more poised and fashion-forward star.


Rihanna fashion

Evan Agostini/Getty Images for Tempo; Larry Busacca/WireImage

Rihanna’s fashion sense has transformed almost as much as her hair! Although the cameras have always loved this chart-topping pop singer, her style is more sophisticated than ever -- including the ravishing red gown she wore to this year’s Grammys on Feb. 10.

Brad Pitt

Brad Pitt fashion

Jim Smeal/WireImage; ALBERTO PIZZOLI/AFP/GettyImages

Brad Pitt has only gotten better with age -- and so has his fashion! It’s not that Brad’s grungy look made us cringe in 1988, but we’re happy to see him donning suits these days. After all, he’s got to keep up with fiancé Angelina Jolie -- and that’s no easy task!

Blake Lively

Blake Lively fashion

SGranitz/WireImage; Jeffrey Mayer/WireImage

Blake Lively was just 17 when she made her acting debut in The Sisterhood of the Traveling Pants, which is why we can’t fault her for the bright colors and rolled-up capris she wore to the Kids' Choice Awards in April of 2005. But it’s Lively’s current va-va-voom style that’s got her turning heads, including the stunning strapless dress she showed off at the premiere of Savages in June of 2012.

Halle Berry

Halle Berry fashion

Jim Smeal/WireImage; Alexander Tamargo/FilmMagic

It seems no one was safe from the embarrassing fashion of the 1980s -- not even Halle Berry! Although her embellished jacket and skirt aren’t the worst fashion crime ever committed, the actress’ current style is much more modern and trendy.

Sarah Jessica Parker

Sarah Jessica Parker fashion

Ron Galella, Ltd./WireImage; Bennett Raglin/WireImage

It’s hard not to transform your style after becoming New York City’s most fashionable journalist on Sex and the City. But Sarah Jessica Parker has taken quite the leap, trading in oversized jackets and funky hats for flattering dresses, like this polka-dotted number she wore in late February with trendy pink pumps. Carrie Bradshaw would be proud!


Beyonce fashion

Kevin Winter/Getty Images; Jason Merritt/Getty Images

Destiny’s Child was right when they said, “I don’t think you can handle this.” Although Beyonce and her groupmates had the bodies to flaunt skin-baring outfits in 2000, it’s the singer’s mature style that we’re envying now, including the black-and-white ensemble she wore to this year’s Grammys on Feb. 10.

David & Victoria Beckham

David Victoria Beckham fashion

Tony Barson/WireImage; Alberto E. Rodriguez/Getty Images for Sports Spectacular

Their style might be a little less skin-baring these days, but David and Victoria Beckham still make quite the sexy couple! Considering Victoria is now a successful fashion designer and entrepreneur, it’s no surprise the former Posh Spice and her hubby are seen in chic dresses and suits these days.

Kim Kardashian

Kim Kardashian fashion

Mark Sullivan/WireImage; Dave J Hogan/Getty Images

Who knew Kim Kardashian had such a seriously unfashionable phase? The giant hoop earrings! The matching boots and purse! We much prefer Kim’s current style, like this yellow gown from May of 2012, which puts her killer curves on display.

Mark Wahlberg

Mark Wahlberg fashion

Ron Galella/WireImage; Jon Kopaloff/FilmMagic

Is that really Mark Wahlberg hiding under all that baggy material? It’s hard to believe, but yes -- Marky Mark really did think he looked good in that. We couldn’t be happier to see the Ted actor all cleaned up, especially in a snazzy suit at the film’s premiere in June of 2012.

Eva Longoria

Eva Longoria fashion

Ron Galella, Ltd./WireImage; Jeff Vespa/WireImage

We can’t believe Eva Longoria ever showed off this much skin! Although the Desperate Housewives actress bared her tummy quite a bit in the late '90s, she’s become known for mature gowns and sleek dresses, much like the one she wore to this year’s Golden Globes on Jan. 13.

Katie Holmes

Katie Holmes fashion

Steve Granitz/WireImage; Bruce Glikas/FilmMagic

She might be mom to 6-year-old Suri, but Katie Holmes has maintained a youthful fashion sense herself throughout the years. Fortunately, the actress has swapped too-tight dresses for classier items, including a flattering blue blazer she wore in NYC on Jan. 10. Suri’s got quite the fashion role model at home!

Jessica Alba

Jessica Alba fashion

Ron Galella, Ltd./WireImage; Alo Ceballos/FilmMagic

Raising two daughters has been a good influence on Jessica Alba’s style! The actress had a penchant for glittery eyeshadow and color coordination back in 1999, but now she keeps it simple and fun, even when she’s running errands.

Sandra Bullock

Sandra Bullock fashion

Jim Smeal/WireImage; Albert L. Ortega/Getty Images

It looks like Sandra Bullock has only gotten more glamorous throughout the years! Now a mom and an Academy Award winner, the actress has ditched her childish sweaters and baggy jeans from 1994 for a more chic red carpet style. Our favorite part? Her footwear! Stylish pink pumps are (almost) always a better choice than chunky boots.

Ryan Reynolds

Ryan Reynolds fashion

Jeff Kravitz/FilmMagic; Jeffrey Ufberg/WireImage

Before he was People's Sexiest Man Alive, Ryan Reynolds was just Average Joe. (Sure, it was the '90s, but there’s no excuse for a soul patch like that!) Fortunately, Mr. Blake Lively has traded in his jeans and T-shirts for a suit-and-tie look, making him one stylish stud today.

Jennifer Lopez

Jennifer Lopez fashion

Albert L. Ortega/WireImage; Jeff Vespa/WireImage

One thing that hasn’t changed after all of J.Lo’s years in the biz? Her killer body! The singer-actress may have covered up with loose sweaters and long skirts back in 1996, but now she’s not afraid to flaunt her curves in form-fitting dresses, like the one she wore to the Golden Globes on Jan. 13.

Connect with Us
Follow Our Pins

Yummy recipes, DIY projects, home decor, fashion and more curated by iVillage staffers.

Follow Our Tweets

The very dirty truth about fashion internships... DUN DUN @srslytheshow http://t.co/wfewf

On Instagram

Behind-the-scenes pics from iVillage.

Best of the Web