Decoding Y2K Fashion: 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.

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.

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2. Snakeskin 

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. However, there are also plenty of accessory options if you're looking for a more subtle way to hop on the trend.

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3. Pinstripe

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

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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.

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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.

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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.

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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.

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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.

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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. Today, it's all about flashing a hint of this — think Jacquemus's SS23 collection.

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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.

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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.

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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.

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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.

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This piece was published at an earlier date and has since been updated.