Sorry, Gen Z, But These Y2K Fashion Trends Are Too Painful To Bring Back

Fashion simultaneously evolves and cycles. Decade after decade, new trends are created while past trends are honored. It’s a beautiful way to connect generations. Which is why I thought it was so cute when Gen Z started posting tributes to Y2K fashion on TikTok.

The bubblegum pink, baby tees, and below-the-hip jeans are quintessential pieces of the era. However, these young, naive, well-intended souls are missing out on some absolutely show-stopping pieces that you could find on every girl in the halls of school everywhere, and even on the red carpet.

Pieces that I have a feeling these Zoomers would never have the gall to attempt to pull off. As an expert of the time period and someone with first-hand experience, here are some of the most daring looks that these TikTok biddies wouldn’t dare to don.

Dress Over Jeans


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A post shared by Ashley Tisdale (@ashleytisdale)

Ashley Tisdale, the queen of layers and Y2K fashion, wore jeans on the red carpet many a time, and many of those times there was a skirt or a dress on top of those jeans. You might think, “did an alien who didn’t understand how to dress their newly acquired human body throw this look together?” And while we’re pretty sure Ashley and her team were never abducted by extraterrestrials, we know now that this look should have never touched down on Earth.

The Longest Shirts You’ve Ever Seen

Hilary Duff at 30th Annual American Music Awards

I’m seeing a lot of crop tops in these Y2K fashion tributes, but it’s just not the truth. The shirts needed to be so long, and then they needed to be pulled down even longer. Not only that, you’d be wearing at least one, if not two or three, even longer tank tops under the long shirt to make the top even longer still. It’s all about the illusion: the illusion that you had five extra vertebrae.


Britney Spears and Justin Timberlake in full denim outfits.

Denim was THE fabric of Y2K. And not like, a jean jacket paired with jeans. The entire outfit was denim. We might not have looked hot, but the thick material definitely raised our core body temperature to an unhealthy degree.

Scene Kids

Was mainstream fashion not your thing? Don’t even worry about it. Y2K fashion has just the alternative look for you: scene kids! There was always a group of kids from your high school who were scene and they all looked exactly like this, complete with raccoon eyeliner and also raccoon hair. For real. And honestly, their confidence sold it, so I’m not even mad at it.

Plaid Bermuda Shorts

O’Connell’s Plain Front Patch Madras Bermuda Shorts

Plaid bermuda shorts made me feel like I was a rich woman on vacation when I actually looked like an Easter picnic blanket. The key with the Bermuda shorts is they needed to be an unbalanced mix of pastels and bright colors that were assaulting to the eye. Pair it with a polo and voilà! Fashiòn!

Cargo Everything

Cargo everything in Pen 15 promo photo.

There was no shortage of pockets in the 2000s. Pants, skirts, shorts, capris, everything you wore on your legs could have extra pockets added to every part of it. The perfect place to keep your collection of lip smackers.


@jennaabarclay Didn’t we alll think gaucho pants & a sequined shrug was ✨timeless✨? #2000s #2000sfashion #2000saesthetic #millennial #nostalgic #00snostalgia ♬ Bossy (feat. Too $hort) – Kelis

Gauchos were super flowy and hit mid-calf length to ensure that your legs could not be flattering in any way. We would pair this with a poncho and really serve some amorphous blob realness.

Trucker Hats


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A post shared by Miss Bel-Air (@doyoulovethe2000s)

Trucker hats were everywhere except for where they needed to be: in the trash. They usually said something insane like a terrible catchphrase or a cheesy brand name, and they never quite fit anyone’s heads. I had a baby pink one that had Napoleon Dynamite’s face on it. I guess I wanted everyone to know that I knew fashion *and* humor.

Belts Over Shirt

Victoria Justice wears belt over shirt.

Victoria Justice

We wear belts to hold up our pants, but with this trend we have completely eliminated the function of the accessory while also making it look worse. 


Pink and blue early 2000s ponchos

The power that ponchos had over us was perplexing. It’s essentially a blanket with a hole in the middle, and in this example, it was completely see-through, so it was almost an accessory at that point. You still had to wear a whole outfit under it. But I’ve said it once and I’ll say it again: Y2K fashion is nothing without its layers.


Fedoras were clearly a crowd favorite in Pen 15 episode.

The only person to ever pull off a fedora is Ne-Yo, but did that stop any of us from getting one on vacation and never wearing it again? Nope! Now it’s your turn to waste your money, TikTok girlies.

This Shirt

If you have never held this shirt in your hands, you will never understand its cottony egg carton construction. When you’re not wearing it, it’s the size of a Build-A-Bear T-shirt but stretches out into this monstrosity. It defied the laws of physics and the laws of fashion.

Scrunched Hair And Straightened Bangs

@overthemoonfaraway Unbrushed curls? She must be dressing to impress. #2000s #millennials #nostalgic ♬ Yeah! (feat. Lil Jon & Ludacris) – Usher

This isn’t exactly fashion, but crusty, crispy gelled hair with pin straight bangs, and heavy lower eyeliner with nothing else, that was the look. Try and make that look good. Just try. I literally dare you.

Ali Hinman
Ali Hinman
Ali is your new gay BFF (they can be girls too, ya know). She is a karaoke queen and a woman of extremes. She throws her opinions around like confetti. No she’s not a crazy cat lady, but yes, she believes that her cat Tina deserves the world and nothing less.