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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 Tik Tok 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 Tik Tok. 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 to dig 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. What I discovered wasn't that there aren't any trends to wear today. In fact, it was the opposite. 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 when 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.

1. Crochet

y2k fashion: gwyneth paltrow wearing a halterneck and jeans with a crochet bag

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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. 

2. Lace-Up 

y2k fashion: lucy liu wearing a lace up jumpsuit

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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.

3. Nice Tops

y2k fashion: liv tyler wearing a nice top and jeans

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

4. Body Chains

y2k fashion: jennifer lopez wearing a body chain

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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. 

5. Feathers

y2k fashion: destiny's child wearing feathers

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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. 

6. Basics

y2k fashion: katie holmes wearing a white t-shirt with a snakeskin skirt

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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. 

7. Baguette Bags

y2k fashion: sarah jessica parker wearing a slip dress and baguette bag

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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 is exactly what I'm talking about. 

8. Loose Tailoring

y2k fashion: jennifer aniston wearing a pair of grey tailored trousers with Brad Pitt

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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. 

9. Chokers

y2k fashion: gabrielle union wearing a pair of leather trousers and pink top with tattoo necklace

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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. 

10. Snakeskin 

y2k fashion: christina aguiliera wearing a pair of snakeskin trousers

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

11. Pinstripe

y2k fashion: salma hayek wearing a pinstripe suit

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

12. Flatform Sandals

y2k fashion: britney spears wearing a pair of flatform sandals

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

13. Rose-Coloured Sunnies

y2k fashion: naomi campbell wearing a pair of rose coloured sunnies

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

Next up, The Biggest Spring/Summer 2021 Fashion Trends to Know

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