Best Celebrity Outfits From the Early 2000s

Picture it: a cropped white tank top, cargo pants, and a pair of platform flip flops. It's an outfit that could easily work for either 2003 or, well, 2023. Y2K fashion trends are (surprisingly!) still going strong, and it seems like every time we say "Oh please, no, let's stop now!" we spot another cringy styling trick from the past being revived (ex: dresses over jeans).

To be honest, the Y2K fashion comeback has grown on us (millennials, for example, now get to wear the '00s outfits they were too young to appreciate). But, if we're going to commit to rocking items such as corset tops and duster coats that remind us of The Matrix, we're going to do it right. That means looking up actual Y2K outfits — as in, what celebrities wore from 1999 through 2003.

Whether the goal is Destiny's Child-level sexy or cool and casual like Angelina Jolie in her Lara Croft era, here's a bit of Y2K fashion inspiration, straight from that period of time.

Jennifer Lopez's Cargo Pants

Since this bottom style is so baggy, choose something tight or cropped to wear up top, like J.Lo's graphic tee.

Jennifer Aniston's Suit

This look is still a red carpet and event favorite, and you don't have to be a celebrity to pull it off. We love how the actress skipped the shirt and added a statement necklace instead.

Devon Aoki's Sweater Dress

If you're searching for cute winter outfits, try this timeless, model-approved formula: a printed sweater dress, styled with knee-high boots and minimal accessories.

Destiny's Child's Floral Outfits

We can't decide which outfit we love more: Beyoncé's flower top and sparkly pants, Kelly Rowland's floral-printed ensemble, or Michelle Williams' sweet matching skirt set. Honestly, we'd still rock every piece.

Angelina Jolie's Leather Pants

Turn faux leather pants into a statement piece by balancing them with a solid T-shirt and coordinating boots, just like Jolie.

Janet Jackson's Maxi Skirt

If you've grown tired of micro-minis, take a tip from Jackson and reach for a maxi instead. A shirt with bold sleeves and boots will make this bottom work for cooler weather, but come summer, a tank and strappy sandals make the perfect replacement.

Aaliyah's Dress-Over-Pants Outfit

If you're not yet sold on this Y2K fashion trick, experiment with a long, sheer tunic on top, similar to what Aaliyah wore to the premiere of Romeo Must Die. For a subtler take, swap the sequin styles for basic alternatives.

Sarah Michelle Gellar's Halter Top

A silky, solid halter top will look great with almost any pair of pants — even shiny blue, snakeskin designs.

Katie Holmes' Jeans

If you're still stumped about what shoes to wear with wide-leg denim, Y2K outfits are a source of inspiration. These jeans were often paired with sleek black boots with a small heel, much like what Holmes wore at the 2002 MTV Movie Awards.

Jessica Simpson's Pink Dress

A sweet tank dress styled with matching heels is the Y2K way to nail date night fashion. Keep the accessories simple and carry a cardigan or duster in case you feel cold.

Kaley Cuoco's Brown Outfit

Celebrities have been trading their jeans for trousers as of late. If you're still unsure what to wear up top, choose something in a coordinating color for a sleek solution that will elevate these basic bottoms.

Victoria Beckham's Corset Dress

Victoria Beckham may have worn this lace-up corset dress to a Y2K awards show (specifically, the 2003 MTV Movie Awards), but in 2023, we'd pair it with a cardigan and boots for a fun date night look.

Christina Aguilera's Metallic Set

We love a pre-made outfit (AKA a matching set) and stylists agree that in 2023, metallics will be worn casually, too. This whole look feels like something Megan Fox would wear on a night out, but a hot pink or bright blue option might make things feel more modern.

Busy Philipps' Tube Dress

You know who loves a long skirt and boot combo? Today's top style icons. We'd admittedly copy Philipps' fashion formula from head to toe — and yes, that includes the tube top.

Mary-Kate and Ashley Olsen's Casual Outfits

The Row designers are still big fans of rocking long coats with sporty sneakers, and now that we've ditched slim-fitting jeans for wider-leg options, this outfit feels like a fresh and fun everyday look.

Sandra Bullock's Black Dress

A black dress could be considered more of a classic than a Y2K fashion trend, but the piece is definitely being seen in a new light for 2023. As we dream up all the ways to style an LBD, we'll be keeping Bullock's ensemble in mind — especially the fringe at the bottom, which is another detail that's bubbling back up.

Brittany Murphy's Pleated Skirt

There's no shortage of schoolcore street style, but the archives hold a ton of outfit inspiration, too. Case in point: Murphy's pleated skirt, which she wore with a bomber jacket and knee-high boots for 2003's Cadillac Super Bowl Grand Prix.

Christina Milian's Denim-on-Denim Outfit

Denim-on-denim is still one of our favorite ways to wear jeans, but if you're looking for something sexier than an oversized jacket and flares, copy Milian's corset and mini skirt combo. Weirdly enough, it contains pieces similar to those we've shopped on Revolve.

Lucy Liu's Leather Duster Jacket

Long, oversized duster coats have become a go-to for stars such as Hailey Bieber. These days, we'd skip the scarf, but other than that, Liu's look wouldn't feel out of place on today's top models.

Britney Spears's Tracksuit

Velour tracksuits are one of Y2K's most recognizable fashion trends, so naturally, we noticed when SKIMS, ALO, and Aerie began selling them again. Now, the laid-back (yet weirdly elevated) look is being worn by everyone from Lindsay Lohan to The White Lotus's Adam DiMarco.

Halle Berry's Red Dress

We saw the rise of tomato soup red in 2022 and the color trend has been going strong since. Between Doja Cat's Swarovski crystals look, Margot Robbie's Valentino dress, and Priyanka Chopra's British Vogue cover, celebrities are loving this specific shade, and we know that Berry's ruched red dress from the Gothika premiere would fit right in.

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