10 Stylish Y2K Outfits That Define the TikTok Aesthetic

I was wearing Y2K trends the first time they came around, and boy, would you have liked to see my collection of halter tops, choker necklaces, baggy jeans and pointed slingback shoes with stumped toes. (Let's face it: I was probably a little inexperienced at walking in heels.) It was a time when dressing was truly fun, even if I probably looked horrendous 99% of the time. The big question is, would I re-wear these pieces now? Because of TikTok, it's something I have to legitimately ask myself.

Thanks to the social media platform and the fact that the early 2000s were 20 years ago, there's a current revival of everything related to Y2K fashion. According to a Stylight report, "these turn-of-the-millennium trends are booming thanks to Gen Z discovering and showcasing them on TikTok." It's a compliment, really, that the young and hip people of today regard my generation's style as aspirational. That's what they're saying, isn't it?

Admittedly, I was scared when Y2K fashion first came back around. I wouldn't even say that I got it right the first time around, so why would I repeat the same mistakes now as a seasoned, 30-something fashion editor? While I managed to avoid it long enough, the pull of nostalgia has proven too tempting to resist, so I set out on a hunt for Y2K outfits I could see myself in, courtesy of some influencers who have already embraced the movement.

Keep scrolling to see the ways in which you can channel late '90s- and '00s-inspired Y2K outfits.

1. Leather Coat + Cropped Knit + Low-Rise Trousers 

Style Notes: The Matrix's influence on fashion should never be underestimated. The iconic 1999 film is solely responsible for the influx of leather coats that ruled at the turn of the century. Add low-rise trousers and a crop top to further enhance your Y2K aesthetic. 

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2. Denim Bustier + Bootcut Jeans

Style Notes: I only need to type the words "Britney Spears," and an image of her iconic all-denim outfit flashes before my eyes. Make this look your own with a fresh take on double denim. Try pairing a bustier with bootcut jeans. 

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3. Pleated Skirt + Short-Sleeved Shirt + Socks + Loafers

Style Notes: Preppy outfits dominated the 2022 runways, but the look has deep roots in the '90s thanks to all those teen movies that came out during that time. (If you haven't seen it, She's All That is finally streaming on Netflix, and I would highly recommend.) Will a pleated skirt, tube socks and chunky loafers become your new Y2K uniform? 

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4. Handkerchief-Hem Dress + Wedge Heels 

Style Notes: When it comes to Y2K dress trends, none speak "throwback" more than handkerchief hemlines. Pair yours with simple mule wedges for main-character, 13 Going on 30 energy. 

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5. Sporty Vest + Loose Trousers + Cow-Print Bag

Style Notes: if you're unsure how to kick-start assembling your Y2K outfit, you only need to look to the Spice Girls (and digital creator Oluwaseun) for guidance. Throw on a sporty vest, loose trousers and a smattering of statement animal print, and consider your life and wardrobe spiced. 

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6. Mesh Top + Miniskirt + Pointed Knee Boots

Style Notes: The overlap between Y2K fashion and punk fashion is blurred, so why try to define it? Fuse the two by pairing a mesh printed top with an edgy leather skirt and pointy boots for a vamped-up take on the aesthetics. 

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7. Shrug + Vest + Cargo Trousers 

Style Notes: Cargo trousers are one of the easiest and, admittedly, least-daunting ways to tap into the Y2K trend without much commitment. Once you're comfortable wearing them, I suggest adding a discernibly '90s shrug into the equation. 

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8. Fitted Minidress + Shoulder Bag

Style Notes: Another staple up for consideration is the minidress—specifically a tight-fitting minidress. Just add a shoulder bag (preferably in nylon), and you've just assembled the perfect Y2K-inspired going-out look. It's as easy as that. 

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9. Oversized Shirt + Sparkly Top + Ripped Jeans

Style Notes: The jeans-and-a-nice-top outfit equation was born out of the '90s and therefore falls into the Y2K aesthetic. Right now, I'm seeing lots of Gen Z influencers wearing rhinestone or chainmail tops with bleached, ripped denim. If you wan more coverage, simply layer on an oversized shirt. 

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10. Cropped Cardigan + Tube Skirt

Style Notes: Tube dresses might be making a comeback, but can I please draw your attention and appreciation to the tube skirt? Yes, I might have worn it to school, but now, the humble buy is making waves on social media. It's most commonly styled with cropped cardigans, the sort you'd find in the Clueless costume department. 

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Next Up, The Autumn 2022 Shopping Guide: Where to Buy the Biggest Trends of the Season