32 ’00s Trends We Love

The 2000s were pretty maligned as a fashion decade. That’s not to say that there weren’t some tough sartorial moments—in the late ’90s, stars were starting to use the red carpet as their personal runway, and the ’00s really upped the ante for shock value. But leaving aside some of the barely-there minis with Uggs and other strange combos we favored, there are some fun style pieces we can lift out of the decade. In fact, the “dressing like it’s Y2K/the 2000s” aesthetic came back into popularity in the early 2020s, with people picking the best, most iconic pieces from that decade and giving them a modern spin. I realize this might sound ridiculous—but some ’00s fashion trends really can become a part of our classic capsule wardrobes.

Below, 32 ’00s trends that we love.

Fedoras

There were a few notable “red carpet hat trends” in the ’00s, including the newsboy hat, beret, and trucker hat, but none was more popular—at least as far as Britney Spears was concerned—as the humble fedora. And, if we’re being totally honest, she rocked it.

Flares

Leaving aside the fact that the low-rise pant isn’t for everyone, the ’00s took our ’90s love of flare pants and took it up a notch—usually with a wider, longer length at the bottom. We’ve loved flares since the ’70s, but this version is a particularly nice update on a classic.

Pants as an Under-Layer

This trend is, in a word, divisive: Plenty of the “’00s worst trends” lists include the mandatory “formal dress over a pair of jeans” look. But it doesn’t mean this trend is impossible to achieve; As with Heidi Klum here, the trick is to pick two pieces that look intuitive together, like this shirt dress worn open.

Shorts and Wellies

Was there anything more iconic than Kate Moss attending the Glastonbury Festival in short shorts and wellies? In the ’00s, this was the fashion girl look. There’s a particular context for this outfit (it’s not something you’d wear to a nice dinner), but for mud or grass, this is perfect.

Crop Tops

The crop top existed long before the ’00s got ahold of it, but this was the crop top decade. We have some…interesting deployments of it, but we also have Mariah Carey looking adorable here in a color blocked outfit. Whether that particular item of clothing is “in” or “out,” the ’00s has plenty of inspo if you like it.

Cropped Jackets

The ’00s were often about layering in interesting ways, including a short jacket with a longer top underneath. A more modern iteration of this look would be to layer a crop top under a cropped jacket and then utilize some high-waisted jeans, then keep the accessories and pumps.

Chunky Belts

Frankly, I love this heart belt on Jennifer Lopez and would wear this look tomorrow. (Rhinestones: Another ’00s trend we like!) A statement belt is a classic element for your everyday wardrobe, but when it’s whimsical or silly, you just want to keep the rest of the look neutral.

Long Scarves

The scarf as accessory, instead of warm weather staple, was a ’00s mainstay. We love the edgy skull pattern here, and the only update to make would be to wrap it around your neck a couple times and match it with something else that’s orange in your look—your shoelaces, nail polish, or similar.

Chunky Jewelry

Obviously, chunky jewelry has been around forever, but the ’00s saw us going with mixed materials—metals with glass, plastic, or crystal, as with Alexa Chung and her skull-adorned necklace here. The big clear drops might look dated, but it’s okay to mix silver and gold in one piece.

Graphic Tees

Paris Hilton, rocking this Forrest Gump-esque shirt, is demonstrating how a graphic tee can be a fun upgrade from a classic shirt. Here, Hilton is probably making a snarky comment to paparazzi, but I kind of love rocking this kind of positivity in your everyday wardrobe.

Midi Skirts

The ’00s trend everyone loves to discuss is the mini, but the midi skirt got some serious love too. We often saw the ’00s skirts end around knee-length, which can be tricky to pull off, but when it was worn below the knee with boots that came up to match, it looks especially fab.

Oversized Sunglasses

Oversized shades have been with us almost as long as we’ve had fashion sunglasses, but the ’00s took the look and made it wonky: Weird shapes, bedazzled frames, mismatched with the overall look (as with Kirsten Dunst) here: It was all happening. Pick a “surprising” pair and wear one today!

Rompers

Even though you might associate the romper with the ’10s, it began to take hold in the ’00s. (After all, if J. Lo wears one, that’s usually a sign it’s about to become popular!) Thanks to the glittery accessories and sleek hair, the look doesn’t have to skew too “youthful.”

Bucket Hats

Never has there been an item of headgear more discussed than the bucket hat. If you love it, you’ve been waiting for the right moment to bring it out. If you hate it, you’ll never wear it. So let your own preferences be your guide, and just break it out when it’s not too cold.

Vests

Granted, this is a costume from Sex and the City, which is arguably one of the more fashionable shows in modern history (so this is not your average streetwear look, in other words). But I still love it as a layering option—whether you’re matching it to your pants or just throwing it on over a tee.

Handkerchief Skirts

The handkerchief skirt can be a maxi, midi, and miniskirt all in one garment—but, to keep it from looking dated, make like Gabrielle Union here and keep the hem generally one length. Then, keep the rest of the look simple and neutral, letting the skirt be the standout.

Low-Rise Jeans

You either loved or hated the low-rise jeans of the ’00s (I happen to be in the latter category because I have thin hips). Thankfully, jeans have evolved in the intervening years, and the new low-rise pants won’t just slide off your body—and they’re not quite as low as they used to be.

Miniskirts

The pleated mini had a real redemption arc in the early 2020s, especially via influencers on TikTok and Instagram. This look on Rihanna could absolutely work today, but if you’d rather not be so ab-forward, just take a long chunky knit top and layer it over your skirt.

Studded/Patterned Denim

Destiny’s Child made it cool to match your outfit with your bffs. Actually, there’s not much you’d need to do to update these looks; If you like a longer length on your denim, choose a pair of jeans with a longer inseam and no slits. And you can always go for bedazzling in your tops!

Chunky Boots

Chunky boots never went out of fashion, per se, it’s just about how you wear them. The ’00s gave us surprise boot pairings, as with this more feminine, folded miniskirt on Gwyneth Paltrow. To modernize, just make something in the rest of you look bulkier and black, like a blazer.

Cargo Pants

This look on Britney is just so cute, and she’s actually balancing out top and bottom effectively. Using a faux fur jacket and top that’s feminine, then leaning into a chunkier, heavier vibe in the pants, then taking it back to delicate in the shiny shoes is actually cohesive.

Tunics

A shorter jacket and a long top underneath: Peak ’00s! There’s ways to make this look dated, but there’s also ways to make it look classic. Keep the length of the tunic not too long; It should just peek out underneath the jacket. Opt for a pair of pants in a similar color.

Rhinestones

We really wanted to sparkle in the ’00s, ya know? Nelly Furtado here has sparkly nails, eyeshadow, earrings, jewelry, AND outfit. You don’t need to do that much (unless you want to!) so pick one or two and really lean in. An easy way is to grab a bedazzled tee and just rock it.

Wallet Chains

Much like a chunky belt, the wallet chain is one of those surprising, counterintuitive pieces that, when deployed effectively, can bring a look together. Britney Spears wears hers messily, but the key is to have yours look sleek (and match with your belt, as she does).

Trucker Hats

The trucker hat of the ’00s was made graphic and feminized so as not to look too jarring with the rest of an outfit (it could still look jarring, tbh, but that’s another story). Since it’s an unusual shape, match the color to your shoes to tie the look together. Or, go for a heavy baseball cap instead.

Tube Tops

The tube top was the slightly more conservative older sister to the crop top—like, if you didn’t want to show that much stomach, the tube top was your friend. It’s a fabulous layering piece; Seriously, put it under a big, heavy blazer and see how great it looks.

Platform Shoes

While never “out” of fashion, it felt like we got tired of platforms after wearing them every day in the ’00s. But the platform espadrille, as Kate Moss is wearing here, is truly a timeless piece. And if you don’t want to lean in on the chunkiness, just opt for a sleeker shape.

Boyfriend Jeans

Long, slouchy, tapered, cuffed: The boyfriend jean was everywhere in the ’00s. Now, it’s basically just considered a classic piece of denim, no different than the skinny or wide-leg, but the boyfriend jeans of today also come in high-rise and more tailored shapes.

Butterflies

It didn’t really matter where: On tops, pants, shoes, and accessories, butterflies were everywhere. (And we got a little tired of them by the end of the decade.) Now, as with everything else on this list, it’s all about moderation. A little butterfly clip is the cutest touch to your look.

Shoulder Bags

Whether sleek and structured or soft and colorful, a shoulder bag was on everyone’s shoulder in the ’00s. If you like shoulder bags already, you’ll know that you can wear them anytime. But if you’d like to dip a toe into the style, go with a big similar to Hilton’s: simple, neutral color, sleek.

Chunky Necklaces

Why wear one of your necklaces from your jewelry box when you can wear allllll of them? Kate Beckinsale is giving us the blueprint for how to make it work: Have all the pieces kind of go together, and use varying lengths so they look complementary and feel delightfully jumbled.

Column Dresses

To a degree, the Calvin Klein-esque column dress of the ’90s was replaced by more body-con styles in the ’00s and ’10s. But the red carpet (and sometimes runway) still gave us some gorgeous iterations of the classic style. You could wear this anytime—just hem it if you don’t like the pooling at the bottom.

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