Decoding Y2K Fashion Trends: Here’s What Actually Looks Good 20 Years Later


I’m old enough to remember Y2K fashion the first time around. I can still vividly recall the cowl-neck black top I wore with my knee-length stonewash denim skirt and a choker for New Year’s Eve 1999. I loved that outfit at the time, and 14-year-old me was very happy about it, but I know there isn’t much from it I’d wear today. However, thanks to TikTok and the fact that the 2000s were 20 years ago, there is a current revival going on 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. While I’m not keen to re-create much from my wardrobe from that era, there are plenty of other trends that still look good today.

I delved into the archives and dug up some of the best celeb outfits from that time to showcase just what I mean. While it might seem very particular, I’m looking at outfits from around the 1999/2000 mark, as this is the best way to find the most Y2K looks. I discovered that there are actually plenty of trends to wear today. I also found it interesting that fashion around the turn of the millennium wasn’t very extravagant. Pre–Lady Gaga (she released her first single in 2008), everything seems pretty low-key in regard to red carpet looks. This was also the time when Dawson’s Creek was big and The O.C. was far from hitting our screens. Late-’90s fashion still had its influence, but there was a newer, more polished look coming in, too. Keep scrolling to see the Y2K trends that still look good today.

Style Notes: A surprising trend, crochet spans decades and still looks good with whatever you wear with it. This is the classic Y2K pairing of jeans and a nice top, with the statement bag adding a little extra. 

Low-key Y2K luxury is a designer crochet bag. 

Style Notes: Strings are back this season, including the G-string (but not as you know it). Here, Lucy Liu is wearing what looks like a lace-up jumpsuit. Today, it’s all about flashing a hint of this—see Jacquemus’s latest collection.

A very cost-efficient way of tapping into the trend. 

Style Notes: There are few celebrities who avoided this look during Y2K. The nice-jeans-and-a-top outfit was a go-to for even red carpet events, as proven here by Liv Tyler. 

From the color to the texture, this top feels intrinsically Y2K. 

Style Notes: Jennifer Lopez was known for plenty of outfits during this time, and while most people were fairly restrained on red carpets, she wore that green Versace dress. But the trend that is coming back today? The body chain. 

A Y2K jewelry trend that feels quite polished. 

Style Notes: While head-to-toe extravagance wasn’t necessarily embraced, details were. Rhinestones, gems, and feathers were always present on the A-list at this time. We’re still seeing feather trims going strong today. 

Wear with a cropped cardigan for optimum Y2K appeal. 

Style Notes: With the more pared-back styling of the ’90s hanging over our heads around Y2K, minimalist looks were often embraced for the red carpet. Case in point: Katie Holmes wearing a white T-shirt with a pencil skirt and strappy sandals. 

Our editors love this classic tee. 

Style Notes: It’ll come as no surprise that Sarah Jessica Parker was the one trying to push the fashion boundaries around this time, and it was often hard to know where Carrie Bradshaw’s wardrobe ended, and hers started. This brightly colored bag is exactly what I’m talking about. 

Staud’s beaded-bag offering just keeps getting better. 

Style Notes: The king and queen of casual-but-chic outfits were Brad Pitt and Jennifer Aniston. These loosely tailored pants on Jen An were the epitome of Y2K styling. 

This entire suit is a wise style investment. 

Style Notes: Find me someone who says they didn’t own a tattoo choker, and you will have found yourself a liar. Nearly everyone owned some kind of choker at this time, and thanks to brands like Roxanne Assoulin, they’re back.

An easy way to bring more joy into your daily wares. 

Style Notes: While Christina Aguilera might have some questionable outfits from the past (let’s avoid all the chaps talk), these snakeskin pants are absolutely something I would wear today. 

You needn’t opt for bright colors—monochrome snake print will also nail the aesthetic. 

Style Notes: The corporate world really bled into late-’90s styling, with pinstripe being a fixture for plenty of A-listers. 

I’m picturing wearing this with blue straight-leg jeans and mules. 

Style Notes: There are so many flatform sandals around right now. 

Mule flatforms? Shoes don’t get much more Y2K than that. 

Style Notes: After some new sunnies? Well, good news: Y2K has your back. Rose-colored glasses, as seen on Naomi Campbell, are sure to make a comeback. Try finding some rimless ones for the real Y2K effect. 

The thin gold frames make these throwback shades feel so premium. 

This post originally appeared on Who What Wear UK, and has since been updated by Jasmine Fox-Suliaman.

Next Up: All of the ’90s Fashion Trends That We Still Love Wearing Today

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