Decoding Y2K Fashion: Here's What Actually Looks Good 25 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 25 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.
Y2K Fashion: 13 Y2K Trends That Define the Aesthetic:
1. Loose Tailoring
Style Notes: The king and queen of casual-but-chic outfits were Brad Pitt and Jennifer Aniston. These loosely tailored trousers on Jen An were the epitome of Y2K styling.
Shop the Trend:
2. Snake Print
Style Notes: While Christina Aguilera might have some questionable outfits from the past (let's avoid all the chaps talk), these snaketrousers are absolutely something I would wear today. However, there are also plenty of accessory options if you're looking for a more subtle way to hop on the trend.
Shop the Trend:
3. Pinstripe
Style Notes: The corporate world really bled into late-'90s styling, with pinstripe being a fixture for plenty of A-listers.
Shop the Trend:
4. Nice Tops
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.
Shop the Trend:
5. Feathers
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.
Shop the Trend:
6. Basics
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.
Shop the Trend:
7. Baguette Bags
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 coloured bag demonstrates exactly what I'm talking about.
Shop the Trend:
8. Chokers
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 Mango, they're back.
Shop the Trend:
9. Lace-Up
Style Notes: Strings are back, including the G-string (but not as you know it). Here, Lucy Liu is wearing what looks like a lace-up jumpsuit and you'd see similar to this on a night out today.
Shop the Trend:
10. Body Chains
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.
Shop the Trend:
11. Rose-Coloured Sunnies
Style Notes: After some new sunnies? Well, good news: Y2K has your back. Rose-tinted glasses, as seen on Naomi Campbell, are sure to make a comeback. Try finding some rimless ones for the real noughties effect.
Shop the Trend:
12. Crochet
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.
Shop the Trend:
13. Flatform Sandals
Style Notes: There are so many flatform sandals around right now, particularly as we head into the warmer months. We can't help but feel nostalgic when we spot this trend out and about.
Shop the Trend:
-
I Thought I Hated '00s Fashion, But These Throwback Sandal Trends Are Actually Chic
Serving Y2K realness.
-
Suddenly, Jennifer Lopez's Favourite Summer Shoe Trends from the '90s Are Back
I'd legitimately wear them all tomorrow.
-
Fashion People Are Accessorising Like It’s 2008 Again—I'm Road-Testing These 7 Trends
Even our bags have bags!
-
14 Rachel Green Outfits We'd Happily Wear in 2025
Friends' resident fashion girl is still our style inspiration.
-
I'm a Denim Expert, so I Already Know Skinny Jeans Are 2025's Hottest Comeback Trend
Read my deep dive.
-
Sorry, But the '90s Did Leopard Print Better—6 Looks Inspiring My 2024 Wardrobe
The best era.
-
If You Love the '90s and French Style, These 8 Outfits Will Speak to You
The best of both worlds.
-
4 Divisive Y2K Trouser Trends Celebrities Are Wearing Over Classy Wide-Leg Pairs
A nostalgia hit.