Imagine: a white crop top, cargo pants, and a pair of platform flip-flops. It’s an outfit that could have been worn in 2003, or it could be today. Whether it’s Gen Z’s love of trends, Millennial nostalgia, or simply the natural cycle of [insert item here] coming back into style and then going out of style again, Y2K style is experiencing a resurgence. And while some of the decade’s trends are somewhat questionable, there are fresh, modern ways to wear early 2000s fashion. I mean, if we’re going to wear things like corset tops and Matrix-inspired anthers, we might as well do it right. That means seeking out real Y2K outfits—what celebrities wore from 1999 to 2003. Whether you’re aiming for Destiny’s Child-level sexiness or cool and casual like Angelina Jolie in the Lara Croft era, here’s some Y2K outfit ideas fashion inspiration straight from the celebrities who shaped this era.
Jennifer Lopez Cargo Pants
Because this bottom style is pretty loose, opt for something fitted or cropped on top, like a baby tee like Jennifer Lopez’s. A suit will also work, especially if you want more coverage. Add cool sneakers to complete the look. Jennifer Aniston’s Shirtless Suit
Jennifer Aniston Shirtless Suit
This look is still a red carpet and event favorite, and you don’t have to be a star to pull it off. We love how the actress skipped the shirt and instead added a statement necklace. It’s simple, yet stunning. Devon Aoki Sweater Dress
Devon Aoki Sweater Dress
If you’re looking for cute winter outfits, try this timeless, model-proven formula: a patterned sweater dress styled with knee-high boots and minimal accessories. This outfit was a hit in the early 2000s and can work today. Add statement shoes to accentuate the look.
Floral Outfits for Destiny Child
We can’t decide which outfit we love most: Beyoncé’s floral top and sparkly pants, Kelly Rowland’s floral ensemble, or Michelle Williams’ cute skirt and top set. Try any of these looks today and you’re sure to get tons of compliments. It’s a blend of Fairycore and Y2K at its best.
Angelina Jolie Leather Pants
Turn leather pants into a statement piece by balancing them with a monochromatic tee, just like Angelina Jolie does. Simple accessories, like the studded belt and black heeled boots, keep the edgy theme of the aesthetic. Finally, apply matte makeup to bring Jolie’s outfit to life.
Janet Jackson Maxi Skirt
If you’re tired of micro minis, take a cue from Jackson and opt for a maxi instead. A statement-sleeved shirt and boots will make this outfit suitable for cooler weather. In the summer, the ideal replacement would be a tank top and strappy sandals.
Aaliyah Dress-Over-Pants Outfit
Dresses over pants are a controversial topic, but here’s proof that it works. If you’re still unsure about this 2000s fashion trick, experiment with a long, sheer tunic like Aaliyah’s. For a slimmer option, replace the sequins with more basic choices, such as a sheer or knit top. Sarah Michelle Gellar’s Halter Top
Sarah Michelle Gellar Halter Top
A silky, plain halter top will suit almost any pants, even bright blue snake-print trousers. This outfit is a great option for a date or a night out with friends. If you prefer a simpler look, replace the snake-print trousers with your favorite jeans. Katie Holmes’s flared jeans
Katie Holmes Flare Jeans
If you’re still unsure what shoes to wear with denim, take inspiration from 2000s outfits. Pair flared jeans with chic black boots and opt for a small cup heel, just like Holmes did at the 2002 MTV Movie Awards. Jessica Simpson’s pink dress
Jessica Simpson Pink Dress
A cute sleeveless dress with matching heels is a surefire way to look 2000s style. Don’t overdo it with accessories and bring a bolero or tippet along in case you feel like it. Add your favorite shoulder bag, and you’re good to go. Kaley Cuoco’s monochrome brown
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