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Graphic Tees

A graphic long tee and baggy pants were an unofficial weekend uniform in the ‘00s. The casual celeb version was just slightly fancier – i.e., whatever fringe is happening over on Mandy’s shoulder.
How to wear the graphic tees trend in 2025:
Consider graphic tees the new band tee. Keep it simple with a short sleeve boxy silhouette and wear with everything from jeans to slip skirts.
Shoulder Bags

SJP, Y2K fashion It girl, and her fictional counterpart Carrie Bradshaw are solely responsible for the shoulder bag trend. Life was simpler in the 2000s, flip phones were small enough to fit in the tiny accessory along with your lip gloss and keys.
How to wear the shoulder bag trend in 2025:
Bad news for ppl who like to bring everything and the kitchen sink out with them. From Coach to Marc Jacobs, the classic shoulder bag is popping up everywhere. You could even try and bag yourself a vintage original from eBay! This time, though, rather than matching to your shoes, let your bag elevate your outfit.
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Micro Mini Skirts

The little flare on these mini skirts made them sort of like peplum skirts… but without the skirt part. Yep, it’s verging on belt status. Paris Hilton’s outfit is peak ‘00s when accessorised with a baker boy cap, shoulder bag (see above), a diamnté mesh belt (we told you belts were everywhere) and mule wedges.
How to wear the micro mini skirt trend in 2025:
Nowadays, the micro skirt trend is usually balanced with an oversized top. You’ll also find slightly longer hemlines – think a tennis skirt vs. a full-on micro mini.
Waistcoats

Ciara at the VH1 Save the Music event in 2006 is giving us the perfect example of the waistcoat-as-shirt look (either over a bra top or tee) that was the look in the ’00s. Also, peep the fingerless gloves, people.
How to wear the waistcoat trend in 2025:
The key to nailing waistcoats today is to wear them buttoned up and with a minimal bottom half, either jeans or coordinating tailored trousers for a suit look. Avoid embellishment at all costs, unless you’re heading to a festival.
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The Platform Shoe

It’s not like the ‘00s *discovered* platforms, per se, it’s just that basically every shoe had a huge chunky heel, from flats to the most summery wedges. This includes Jessica Alba’s *sandals but make them super-thick* vibe.
How to wear the platform trend in 2025:
These days, give your ankles a little bit of a break with a flatform sandal, otherwise wooden clog platform sandals offer a more modern silhouette.
Rhinestones

Ah, yes. The sparkly (and kinda cheap-looking?) glitter was stapled onto all ‘00s clothes. Trust, there are still a few rhinestones on the floor of your closet. JLo is serving a slightly more elevated take with a subtle, all-over look instead of a twee tee adorned with individual sparkle gems.
How to wear the rhinestones trend in 2025:
You don’t have to go too far to find rhinestones these days. Opt for subtle touches, like seam-embellished jeans or bejewelled buttons that offer just a small touch of glimmer.
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Bucket Hats

All hail Missy, TBH. This pea green sitch should not work, but the studded decoration everywhere (including on a fun bucket hat to make it feel more casual) absolutely does it for me.
How to wear the bucket hats trend in 2025:
Bucket hats have been around for a minute, but you have our full permission to jazz yours up by sewing some patches or rhinestones on it. Sooo ‘00s!
Low-Rise Jeans

These. Were. Everywhere. Eva Longoria wore a pair of these jeans to the ABC primetime previews, and her skinny pink belt helped emphasise just how low they were.
How to wear the low-rise jeans trend in 2025:
Back in the day, they were designed to show off your abs and featured on figure-hugging silhouettes like skinny and bootcut styles. These days, low-rise jeans are a bit more comfy, accompanying baggier and wide-leg denim.
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Pointy Below-the-Knee Boots
I’m all for a monochrome look, and the reason this doesn’t look totally wild on Mariah here is because she goes for different textures and tones. Even though we know knee-high boots well at this point, that very specific stiletto (pointy toe, hitting just under the knee, tight through the calf) is right out of 2003.
How to wear the pointy-toe boots trend in 2025:
Ignoring the almost-falling-off bomber, a plain slip dress combined with Matrix-worthy brown boots is actually a pretty badass going-out look.
Trucker Hats

In the early 2000s, lots of celebs made their red carpet looks more casual with a trucker hat. Gwen Stefani is giving us some fun energy here, but please let us never revisit the visible white underwear look ever again.
How to wear the trucker hats trend in 2025:
A baseball cap is a fashion girlie essential, IMO. Whether you’re toughening up feminine outfits or trying to delay a hair wash day, stick to block coloured designs with an embroidered slogan on the front rather than a large, oversized graphic design.
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Strappy Sandals

A barely-there sandal was the shoe pick for prom-goers everywhere. Actually, I gotta hand it to Mandy Moore: Modernise the shoe a lil bit, shorten the hemline, and make the curls a smidge less bouncy, and she could totally pull this off today.
How to wear the strappy sandals trend in 2025:
A simple strappy sandal has been around forever, but opt for a simpler strap over the foot and a square toe and boom, you’ve modernised it for this decade.
Baker Boy Hat

I find the rest of Britney’s outfit to be…um…intriguing (we really loved a flouncy tunic top back then), but she’s totally pulling off that hat! It’s the more feminine version of the trucker hat.
How to wear the baker boy hats trend in 2025:
Today, you probably wouldn’t go with baby pink (or the wild jean/boot sitch), but stick to a baker boy hat in neutral hues or a heritage tweed fabric for a country twist, and it’s the perfect accent.
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Crop Tops

The mini and crop top combo was sooooo popular. Fergie has a lot happening here – blazer, belt, leg-warmers and heels feel like several accessories too far – but the black graphic crop top is straight outta 2002.
How to wear the crop top trend in 2025:
Now, you’ve got all the choice in the world when it comes to crop tops. From baby tees to longline cropped tank tops, pair yours with a mid or high-rise waistband. Whenever you’d wear a white or black t-shirt, swap it out with this.
Baby Pink

Head-to-toe tonal is never a bad call, but this level of pink would be challenging for anyone but the master – in this case, we’re referring to Jennifer Lopez. JLo somehow manages not to make a feminine slip dress with a colour coordinating wrap scarf and sandals feel twee.
How to wear the baby pink trend in 2025:
Pastel pink is actually a huge SS25 colour trend, so there’s plenty of choice on the high street when it comes to incorporating this hue into your wardrobe in an item and silhouette that works with your style.
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Faux Fur Coats

The outerwear in the ‘00s had to be just as intense as the rest of your outfit. Case in point: Britney Spears rocking this bright pink faux fur jacket when she received her star on the Hollywood Walk of Fame. More really is more!
How to wear the faux fur coat trend in 2025:
Faux fur has been getting better and better, so there really is no restrictions with this look. Keep it simple in a black mid-length design, go for a statement style in a brightly coloured number or have fun with a leopard print pattern.
A Statement Belt

Beyoncé hit the 2000s fashion trifecta during her appearance on MTV’s TRL. We’re talking low-rise cropped cargo pants with an oversized belt. Bonus points for that wallet chain. You could not have a more Y2K outfit, IMO.
How to wear the statement belt trend in 2025:
You’ll want to match your belt to the cut of your jeans. We love a chunkier belt with high-waisted denim to accentuate our figure. Otherwise, for low-rise silhouettes or when you want a belt to sit low on your hips over a slip dress, you can’t go wrong with a chain belt.
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Lots of Satin

I don’t miss the way it wrinkles immediately when you sit down, but I don’t totally hate Emma’s floor-length number here. The cut might be a bit dated, sure, but the shine and length are both things we brought into the 21st century with our sexy summer dresses.
How to wear the satin trend in 2025:
Less is more – we’d go for a classic satin slip dress, maybe with a cross-strap back for just a little added interest.
3/4 Length Trousers (AKA Pirate Pants)

Did we all seriously think this was a flattering cut? Bubble hems were evidently everywhere, including on cropped trousers, but this baggy fit is really not the one.
How to wear the cropped trousers trend in 2025:
Maybe skip the bagginess and opt for a pair of capri pants or pedal pushers instead. All our favourite high street brands have their own take on the trend, from split-hem black styles to gingham picnic printed designs, but the key to success here is ensuring a close-fit throughout the thigh. A slight flare into a straight-leg below the knee is as loose as you can go.
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Big Sunglasses

We’ll get to tracksuits in just a sec, but the whole ironic sunglasses at night was a fave of ‘00s stars, especially when the sunglasses in question spanned from the mid forehead to past your cheekbones. Honestly, JLo could be headed to the gym, a party, a brunch, or all three here.
How to wear the big sunglasses trend in 2025:
Even though thin ‘90s sunglasses are still the rage, a big chunky pair can feel really substantial and the perfect pair for a summer holiday. Experiment with oversized square and cat-eye styles.
Dresses Over Trousers

This trend – layering a mini dress over floor-grazing jeans – was big with teen actresses, as it allowed them to wear shorter hemlines while still looking family-friendly. Win-win!
How to wear the dress-over-trousers trend in 2025:
These days, I wouldn’t necessarily say jeans under dresses is the look (although I’ve been proven wrong before) but if you did want to recreate this outfit in a modern way, try opting for a longline shirt that can either be worn open or left unbuttoned at the front from the top of the thighs, down.
Belle Bakst is a NYC-based fashion editor and content creator. Her work has been featured in Cosmopolitan, InStyle, Harper’s Bazaar, Brides, and more. When she’s not researching this season’s best shoes, you can find her vlogging a sample sale, or thrifting in Manhattan. Follow @littlefashionstylist on Instagram and TikTok for outfit inspo, vintage jewelry hauls, and the occasional Bergdorf Goodman selfie.

Katherine J Igoe (she/her) was a favorite editor for Cosmopolitan and is a freelancer: lifestyle, culture, and beauty (she’s obsessed with gift guides, best-of movie lists , and beauty products). She’s been a freelance writer and editor for over a decade, collaborating for Marie Claire (2018 to 2021) and Bustle (2021), with bylines in the New York Times, Parents magazine, And sorry. She lives in Boston with her family, and you can follow her on Instagram or Twitte. It’s “I go to dinner,” not “her huge ego,” but she chose to both.
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