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. 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

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.

Bottega Veneta The Pouch Crochet-Leather Clutch Bag (£6165)

2. Lace-Up

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.

Jacquemus La Jupe Terraio Hemp-Blend Maxi Skirt (£475)

3. Nice Tops

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.

Rixo Danica Ruffled Printed Cotton Blouse (£165)

4. 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.

Loren Stewart XXL Silver Body Chain (£315)

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.

Prada Feather and Bead-Embellished Crinkled-Chiffon Midi Skirt (£2130)

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.

Arket Crew-Neck T-Shirt (£15)

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 is exactly what I’m talking about.

Staud Tommy Geometric-Print Beaded Shoulder Bag (£215)

8. 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.

H&M Tailored Trousers (£25)

9. 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 Roxanne Assoulin, they’re back.

Roxanne Assoulin Enamel and Gold-Tone Choker (£120)

10. 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.

Gauge81 Chipata Snake-Effect Faux Leather Flared Pants (£310)

11. Pinstripe

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

MM6 Maison Margiela Pinstriped Tailored Jumpsuit (£830)

12. Flatform Sandals

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

M&S Collection Leather Flatform Flip Flops (£35)

13. Rose-Coloured Sunnies

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.

Ray-Ban Square Frame Sunglasses (£158)

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

This article originally appeared on Who What Wear

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