Why Is ‘Ugly’ 2000s Fashion Making a Comeback? I Tried To Find Out.

You may remember the 2000s as the turn of the millennium, an era of lightning speed tech innovation, or you know, the time fashion went to absolute shit. But a quick scroll on TikTok or Instagram reveals that Gen Z’s coolest kids are now sporting what was previously dismissed as hideous. Since when did terrible trends that people loved to hate — Dress over jeans? Skin-tight animal print tops? Capri pants? — actually became cool? I needed answers, so I reached out to people who were totally owning the Y2K style, and dove deep into an investigation. 

First, what exactly is 2000s fashion? Klaudia, 25, a Singaporean who embraces her Y2K-inspired fashion sense on Instagram, said it’s the complete opposite of the basic normcore fashion that most people wear today. 

“Y2K fashion is quite the opposite of ... minimalistic fashion,” she said. “I'm always allured by louder colors that most people would [stay] away from, I think, such as orange, yellow, and neon shades; and prints-on-prints, chokers, some metal, some beads, funky shades, big earrings, tons of rings.”

Apparently, it has a lot to do with another trend — thrift shopping.

“I believe thrifting could [have] also led to the rise in Y2K fashion because it’s mostly clothes from the 2000s,” said Kah Yu, a 20-year-old student in Singapore whose Instagram thrift shop features characteristically Y2K items such as argyle vests and rhinestone crop tops.

Scouring for pre-loved gems from thrift stores has become a way of life, most notably championed by Gen Z. Besides its affordability, thrifting also comes as a rejection of fast fashion and its negative impact on the environment.

Then there’s the nostalgia factor. 

From the “rare aesthetic” trend to 2014 throwbacks on TikTok, Gen Zs have been ferociously experimenting with nostalgic fashion. According to psychologists, nostalgia is often associated with positive emotions, offering a comforting anchor during stressful times. This perhaps explains why, for many fashion enthusiasts today, going back to Y2K trends amid global uncertainty is their way of going forward.

Lis, a 23-year-old student in London, loves wearing cropped printed tops and little baguette bags. “It’s the era I grew up in, so it feels pretty nostalgic,” said Lis, whose Instagram account documents her everyday street style. 

I too was an impressionable kid during the early 2000s, but I have to say, I don’t have the same predilection for venturing into bold fashion territory. On a normal day, monochromatic outfits and plain tones are my jam.

I do occasionally go thrift shopping for affordable secondhand pieces, but always kept to my fashion comfort zone. But they say don’t knock it ‘til you try it, so I spent an afternoon thrift shopping for interesting Y2K pieces around Singapore and combining them with my existing wardrobe for a 2000s-inspired makeover.

I also had my friends rate my outfits out of 10 and offer their honest feedback. Some were encouraging, others brutal. But all constructive, nonetheless. Now, roll the montage taken from my trusty bedroom.

Y2K has weaved itself into cottagecore, an ethereal aesthetic that’s gently embraced by romantic teens. Drawing inspiration from old Disney cartoons and classic fairy tales, I paired a silky slip with a floral button cardigan — both featuring dashes of pale pink and green. To accessorize, I paired the outfit with a mint green baguette bag and dainty green earrings. I also added a cream satin scrunchie and baby blue bandana to complete the soft, quaint outfit. Wearing this made me feel super cute … and properly craving for a tea party in the woods, sipping, pinky-up, from a tiny antique teacup.

“Very sweet. I think it shows the more feminine side of Y2K. The headband also goes really well with the look,” a friend said. But another friend wasn’t feeling the meadowy vibes: “I think your bandana saved the outfit, which just looks like two sets of pajamas.” 

Well, it’s true — I actually got the dress from the lingerie section. But who says you can’t wear pajamas out and still totally own the look? 

Friends’ rating: 6.5/10

Would I wear this again? Yes, but perhaps in an alternative incarnation. This look is just a little too — for lack of a better word — cottagey for my liking. It would definitely be fun to try incorporating more edgy pieces like silver metal accessories, to contrast with the softer elements of the look.

This outfit featuring a crop top-and-low-rise-jeans combo is all about owning the basic bitch identity. I stuck with a safe blue color and kept things simple. My style inspiration? Musa, the exuberant music fairy from Winx Club. 

This was the most well-received outfit, but probably because it’s also the least adventurous. 

“The low-rise jeans, crop top, and hoops go very well together. I can see Britney wearing this in the early 2000s,” offered a supportive friend.

Truth be told, my mind was set on denouncing the low-rise jeans trend. I was certain I wouldn’t like it. After all, who would want to look like they’re all torso? But I’m actually digging this “jeans sitting precariously low on your hips” mood. It made me feel hella confident.

Kah Yu, who has just started dipping her toes — and her thighs — into the low-rise jeans trend, said her favorite thing about Y2K fashion is its heck-care attitude towards fashion norms and beauty ideals. 

“We can be eating an 8-course meal, having a food belly, wearing low-rise jeans, and still being confident about that,” she said. 

Well, I agree. I’ve had this crop top in my closet for years but have only ever worn it with high-waisted pants, to conceal my belly rolls and avoid making my torso look awkwardly long. But this midriff-baring getup definitely screamed, “I’m comfortable in my body!” which is an attitude I want to manifest.

Friends’ rating: 7/10 

Would I wear this again? Yes! 

With a sequined teal camisole tucked into a gray patterned midi skirt, this is a classic girl-next-door look, infused with Y2K granny chic. I completed it with a tortoiseshell claw clip and baguette bag (in a croc print) — both Y2K essentials. 

My friends had no comments on this one, and I get it — nothing says “I’m boring” like this prudent outfit. But you know what, boring is a vibe too. I can totally see myself strolling around a quiet neighborhood in those croc print mules, engaging in mundane activities like smelling the flowers or exchanging pleasantries with middle-aged neighbors.

Friends’ rating: 5.5/10

Would I wear this again? Yep, I actually really dig the classic modesty oozing out of this outfit. It’s different from what I would usually wear, but in a refreshing way.

For this outfit, I took notes from Klaudia, who suggested mini-sized clothing items and a pair of sunglasses that would suit my face and vibe. In her words: “It's all about the vibe, man.” But NGL, I found myself completely out of my element in the bodycon top and denim mini skirt, staring blankly into the mirror wondering who this leopard-print-wearing, sunglasses-flashing girl was.

This is definitely my most controversial outfit yet — a friend rated this 1/10, while another gave it an 8/10. I guess in keen eyes this could read as a daring, skimpy chic take on the perennially polarizing leopard print, but it could also well be interpreted as a lazy, tacky kopitiam-core getup that would struggle to be associated with fashion. “CUTE! Love the print and the boots,” said a friend. “This outfit makes me angry,” said another.

Friends’ rating : 4.5/10

Would I wear this again? Probably not. I get the charm of this cheeky outfit but when I was sizing myself up in the mirror, all I could think about was how unrecognizable I looked. It’s cute but it’s just not me.

A sharp departure from the out-of-character leopard print fit, this Y2K boyband-inspired look was more my speed. In fact, besides that dark blue top, the entire outfit consisted of items that were already in my wardrobe. The baggy pants, oversized sweater vest, and sneakers — all in dull tones — channelled laidback NSYNC from that press conference when they launched some MSN CD thing (I’m sorry, did these acronyms just ambush you with a wave of nostalgia?).

While this outfit wasn’t spectacular, my friends were pretty much on board with it. “You look so cool in this one,” said a friend. “The pants and shoes, especially; you look like you’re ready to bust out some hip-hop moves.”

Friends’ rating: 7/10

Would I wear this again? Heck yeah. I’m already wearing it again right now.

“The colors here are crazy,” said a friend, “unless that’s the look you’re going for??” Why yes it was. I call this look “the quirky Cantopop queen.” The 2000s were a big time for manic pixie dream girls — those beautiful fascinating girls in movies who seem to exist solely to intrigue and support male protagonists. Here, I’m channeling Cantopop’s very own manic pixie dream girl, Chungking Express-era Faye Wong.

I got decked out in half a rainbow (none of which were my usual colors), butterfly hair clips, and bedazzled sandals; it was go-loud-or-go-home for this one. As eclectic as these elements were, I felt that they complemented one another pretty well. But what really tied the ensemble together was the gray patterned midi skirt, which balanced the loud tones with a touch of classic femininity.

This look was so fun to put together, but it’s probably still a little too out there for most people. My friends unanimously agreed, through their dismal scores, that this outfit wasn’t it. “Your shoes are a no-go; I feel uncomfortable looking at them,” a friend commented. 

Friends’ rating: 3.5/10

Would I wear this again? I think so! I actually quite like the vibrant look of this manic pixie dream outfit, but I’ll probably dial back on the manic and go with a more toned-down pair of sneakers. 

Ah, dress over jeans. The Y2K trend that everyone loves to hate. Except now it’s actually becoming cool again. I don’t think anybody pulled off this trend better than pop stars in the 2000s, so squeaky clean Nickelodeon and Disney mainstays — think 2004 Amanda Bynes and Lindsay Lohan — were my style inspos for this outfit.

I threw on the same lacey cami dress over flared jeans (low-rise, of course) and black leather boots. The result? A very visual representation of the get-you-a-girl-who-can-do-both meme: An upper body that says, “I’m ready to lie on a dreamy meadow doing nothing but twirling a glass of red wine,” and a lower half that says, “I’ve just purposefully brisk walked around the city, running errands, and now I’m tapping my foot impatiently at Starbucks waiting for my Frappuccino.” 

This was another polarizing outfit among my friends, with scores ranging from 2/10 to 7/10. 

“The outfit just feels out of place: jeans and boots with pajamas,” one of them commented. But at least one friend could appreciate this signature Y2K trend. “I think this shows off the jeans-under-dress trend well,” she texted. “Love that the dress is more feminine + the slightly more masculine flare jeans + boots.”

Friends’ rating: 5/10

Would I wear this again? Yes! Totally digging the jarring contrast in this look and how it straddles the line between fashion disaster and sartorial poetry.

What I learned at the end of this short experiment, is that Y2K style isn’t really about specific clothing items. It’s more about the spirit of breaking fashion rules and pushing aesthetic boundaries.

“A lot of Y2K-inspired fits, which I consider to be basic guised as Y2K … are to me an insult to the true essence of the Y2K fashion genre, because you literally see multiple replicates of similar design. Nothing exciting, unique or original about them,” Klaudia told me. 

After playing around these various Y2K styles, mixing and matching my way into creating my own definition of beauty, I can see what she means. And now I have an expanded wardrobe. Nice.