She Wore THAT? 25 Then-and-Now Style Pics From Your Favorite It Girls

Now: Olivia always mixes high fashion with function, and she knows exactly how to show off multiple statement accessories at once. Strappy heels, belts, and fringe clutches complete almost all of her outfits — even the fancier looks.

Then: Olivia still loved to make a statement in a bold print, and she's always favored feminine silhouettes, but her outfits were less risky. When she accessorized, it felt more matchy-matchy.

Now: Rihanna's the new face of Dior, which has caused her to tone down her racier looks for the red carpet. However, she still favors denim, shades, and a really bold shoe.

Then: Rihanna was obviously rocking a body chain way before all the ladies who are wearing them now. She showed hers off with a tie-dyed belly shirt that feels so 2000s and low-slung jeans.

Now: While Kate favors long dresses or jumpsuits, all of which have slight bohemian edge, she never steps out without adding an element of sexy.

Then: Kate's style was just as sexy as it is now, but it was also superfeminine. She chose a silky white bustier set for the 1999 MTV Movie Awards.

Now: The Olsens always manage to stun, even when they're wearing all black. For such petite girls, they make oversize silhouettes look striking on the carpet.

Then: Remember when you collected all of the Olsens' home videos in the '90s? That's when MK and A were hitting up the red carpets in slinky patchwork dresses and matching sandals with chunky soles.

Now: There's nothing Nicole Richie won't try once, so you can expect to see her in sheer dresses, statement prints, and all-white suits that highlight her neon locks.

Then: Back when she lived The Simple Life, Nicole favored going-out tops. She was still showing off bold, sometimes questionable prints, but at least she was patriotic!

Now: Kate's style is streamlined, ultrafeminine, and extremely fashion forward. Bosworth is friends with plenty of designers, and she even started her own line of shoes. You can spot her starting trends on the regular.

Then: In the 2000s, Kate still knew how to match like a pro, and she was totally on trend with this turtleneck and miniskirt ensemble.

Now: Every time J Law steps out, she gets sexier and sexier. For the red carpet, she usually chooses Dior, and she shows skin on the street too!

Then: In 2007, Jennifer was just another blond bombshell wearing strapless, tulle-finished dresses and keeping the heel height low.

Now: When Angelina makes red carpet appearances, she looks like a total siren. The actress usually wears long gowns that feature demure necklines.

Then: No one can forget Angelina's goth-inspired looks from the '90s. Of course, she usually brought them lots of edge, showing off her hip bones in low-waisted jeans or, in this case, throwing on a dramatic velvet cape.

Now: With a toned bod like Jennifer's, who wouldn't want to show it off? The actress always chooses waist-cinching dresses or takes a slight risk with a plunging neckline.

Then: Matchy-matchy looks were all the rage in the '90s, so when Jennifer promoted Friends, she chose silk designs that hit her right above the ankle and easy, complementing sandals.

Now: Kate may slip into an evening gown every now and then, but she never leaves it at that. Everyone's favorite '90s supermodel still practices her signature rocker-inspired style, keeping feathers and fringe in heavy rotation.

Then: When Kate dated Johnny Depp, she made lots of red carpet appearances by his side. While she wore plenty of Calvin Klein slip dresses, this high-fashion sequined gown looked just as effortless with a simple chignon hairstyle.

Now: Victoria wears a lot of her own designs, but she usually tends toward simple black gowns for the red carpet.

Then: One of Victoria's first red carpet appearances was at the 1997 MTV Music Awards in Europe, alongside the Spice Girls. Back then, you couldn't find her showing off a hemline that extended to her knees. It was always about the supertight minidresses and platforms.

Now: Rachel is an undeniable style icon, and her fashion sense has matured since her days on The O.C. Rachel knows exactly how to flatter her petite frame, habitually opting for tailored minidresses and high heels.

Then: While she was always glowing, Rachel wore a lot of long tunic tops with straight-leg jeans and sandals. It's plain to see that she's enhanced her red carpet formula since then!

Now: Kim rarely steps out without showing what seems like too much skin, and her goal is to make jaws drop. Just take this sheer, skintight dress, for example. It's one of the first outfits she wore since announcing her second pregnancy.

Then: Oh, the days of Kim's non-Kanye West-approved outfits! We can hardly imagine her rocking denim on the red carpet now, when there's so much opportunity to show some skin.

Now: Jessica definitely always gears toward the feminine side, but for special events, she doesn't mind showing a sexy slip of leg or a fun print, like this Kenzo design.

Then: Cuffed jeans and oversize sweaters were paired with fun sandals and a delicate handbag. Jessica always looked just as effortless as she does now.

Now: The sexy actress always makes us swoon, and she almost always plays up the shimmer when it comes to an evening gown. Look out for leg slits and high necklines.

Then: Kate was still glowing, and her outfits always felt perfectly put together. Just look at the equal amount of bangles on each wrist!

Now: Blake is a total fashion goddess. On the red carpet, we can't help but gape at her gowns, and she graces her best princess moments with a feminine touch.

Then: Remember when Blake was just another teenager promoting Sisterhood of the Traveling Pants? Distressed denim and fitted short-sleeved tees were red carpet appropriate with matching heels.

Now: What designer doesn't want to dress Emma Stone? She wears tailored, menswear-inspired silhouettes just as well as she does long gowns, and she can pull off just about any color.

Then: When Emma was rising to fame, she opted for flared denim, graphic tees, and dangling earrings.

Now: Jaime's been flaunting her baby bump in flowing feminine gowns that come in bold colors.

Then: Jaime was just another red-carpet-ready star in jeans and a breezy top.

Now: Solange will put on just about any avant-garde design you throw her way, and she always rocks it. Structured shoulders, unexpected cutouts, and colorblock pieces make up her adventurous wardrobe.

Then: In 2001, Solange's style was as bold as ever, but her outfits were definitely a lot busier!

Now: Miranda loves to show off her supermodel bod, but she does it with elegance in mind.

Then: Miranda kept up with the trends when she made her debut on the Victoria's Secret red carpet. Most ladies had one of these distressed miniskirts in their wardrobes!

Now: We maintain the fact that Taylor dresses for who she's dating. Lately, she's been leaning toward daring looks! Cutouts, jumpsuits, and cleavage are the name of the game for the singer.

Then: When Taylor was strictly country, she always chose flouncy, ladylike dresses. When she wasn't getting all matchy-matchy with her accessories, Taylor wore her cowboy boots on the carpet.

Now: Kendall is one of the hottest supermodels of the moment, so she definitely aims to stand out. She loves a formfitting dress, a leg slit, and little details like cold shoulders.

Then: Kendall made her red carpet debut alongside her sister Kylie. Even back then, Kendall knew the power of a leather jacket.

Now: Every time we see Jennifer on the red carpet, she gets a bit more, well, naked. There's no denying she's got gorgeous curves, and she chooses superglitzy designs to play them up.

Then: J Lo has always been big on the sparkle, but at the premiere of Selena, she covered up with a furry shawl.

Now: Emma is one of the most modest style stars, but she always gets it right. Wearing tailored pants and bold silhouettes on the red carpet, she makes the most simply structured designs feel unexpected.

Then: Little Miss Hermione Granger! At the Harry Potter premiere, Emma went for shades of purple and gray. We just can't get over that furry stole!

Now: There's a certain sweetness to Reese's look that even sexy cuts can't take away from. On the red carpet, Reese likes monochrome ensembles. But sometimes she'll stray from the expected with a bold shoe, like these ankle-strap pumps.

Then: Reese has been making red carpet appearances for quite a long time! When she was younger, she was even preppier than she is now, polishing off her outfit with a tucked-in collared shirt.