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The 2000s were a confusing—but fun—decade for clothing and footwear. Jeans worn with dresses, midriffs always bare, and chunky belts with every! single! outfit! While late '90s and early '00s (aka Y2K) trends have made a fashion comeback recently—looking at you, biker shorts and bucket hats—it's kind of a delicate balancing act between channeling the style and putting on a full costume. Think: the difference between layering a fun black choker and just fully leaving the house looking like Simple Life-era Paris Hilton. Also important to remember? There were some truly ~wild~ red carpet fashion moments during that time. If you wanna replicate these fun throwback styles (and you should!!), you have to do it right.
Luckily, as always, celebrities were out there way back in 2000 testing out platform sandals and long scarves, taking one for the team so we can figure out how to do it right two decades later. It'd be easy to laugh at some of these, but actually there are some important style lessons here. So, with that in mind, we've compiled a list of trends that are making it to your fave online retailer (or will be soon, judging by recent runways) with some celebs who channelled them way back in the day. Some of these just need a lil tweak to bring into 2022. Others, well, need a bit more intensive overhaul if you're gonna wear 'em today. Go forth, and wear those crop tops responsibly!!
If there's one thing I loved, it was my Delia's graphic long tee and baggy pants (aka, my weekend uniform all year round). The casual celeb version was just slightly fancier—i.e., whatever fringe is happening over on Mandy's shoulder.
Believe it or not, Delia's is still around (via Dolls Kill) and you'd better believe graphic tees are an important part of the collection. Shockingly, Ed Hardy tees are also making a comeback, albeit in much cuter form.
SJP, Y2K fashion It girl, shows off that strange combo of "long simple dress plus fancy shoes and casual bag"that was an important part of your life if you went to college in the '00s. Matching the bag juuust enough to the shoes is the way to make it feel pulled-together instead of haphazard.
From Coach to Marc Jacobs, the "classic" shoulder bag is popping up everywhere. This time, though, it's a more fun, winking nod to the past, instead of a direct copy of what we used to see.
The little flare on these miniskirts made them sort of like peplum skirts...but without the skirt part. Paris is being very Paris here, but believe it or not this is actually pretty restrained for her vibe (probably because she's not baring her midriff at the same time).
Nowadays, you'll want to channel something a little longer (duh) and sporty—think of it more like a tennis skirt vs. a full-on micro mini. Or, if you're still thinking about the shortest hemline you can possibly pull off, try keeping the rest of your outfit oversized and neutral.
Ciara at the VH1 Save the Music event in 2006 is giving us the perfect example of the vest-as-shirt look (either over a bra top or tee) that was the look in the '00s. Also, peep the fingerless gloves, people.
Vests have since been around for forever, but the key to emulate this look is to go short, have a lil embellishment (sorry, the chains are extra), and order a size up so you can fit whatever underneath it.
The Platform Shoe
It's not like the '90s/'00s "discovered" platforms, per se, it's just that they basically made every shoe with a huge chunky heel, from flats to the most summery wedges. This includes Jessica Alba's *sandals but make them super-thick* vibe.
Ah, yes. The sparkly (and kinda cheap looking?) glitter stapled onto all of our clothes. Trust: there are still a few rhinestones on the floor of your closet. Luckily, J. Lo is showing how to make it look slightly more elevated with a subtle, all-over look instead of punching you in the face with sparkle.
You don't have to go too far to find rhinestones these days. Bebe is making a big ole comeback if you wanna go ~even more~ subtle and just wear a tee with their classic glittery logo.
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.
Bucket hats have been around for a minute, but you can jazz yours up by sewing some patches or rhinestones on it (sooo '00s!) or getting a cute daisy, yin-yang version.
These. Were. Everywhere. Eva Longoria wore a pair of these jeans to the ABC primetime previews—and her skinny pink belt helped emphasize just how low they were.
Back in the day, they were designed to show off your abs (which I have never had), but these days low-rise jeans are a bit more comfy. If your hips are smaller than your shoulders (like mine) grab a belt that fits, so they don't end up sliding right off.
The originator of this trend might have been Justin Timberlake, but lots of ladies made their red carpet more casual with a trucker hat. Good old Gwen here is giving us some fun energy here, but please let us never revisit the "visible white underwear" look ever again.
The OTT baseball cap brings some structure and balance to an otherwise feminine outfit. You'll want something not too dissimilar to Gwen's actually, but pair it with a dress or oversized Oxford.
A barely-there Jessica McClintock sandal was the shoe pick for prom-goers everywhere. Actually, I gotta hand it to Mandy: Modernize the shoe a lil bit, shorten the hemline, and make the curls a smidge less bouncy, and she could totally pull this off today.
A simple strappy sandal has been around forever, but throw on a little embellishment and a square toe and—boom, you've modernized it for this decade.
I find the rest of Britney's outfit to be...um...intriguing (we really loved a flouncy tunic top back then), she's totally pulling off that hat! And it's the more feminine version of the trucker hat if that feels like too much.
Today, you probably wouldn't go with baby pink (or the wild jean/boot sitch), but stick to the classic black—like this one at Revolve—and it's the perfect accent.
See what I mean about the mini and crop top combo? (It was sooooo popular.) Fergie has a lot happening here—blazer, belt, leg-warmers, and heels feels like several accessories too far—but the black graphic crop top is straight outta 2022.
Now, you've got all the choice in the world, including plain crop top tees and racerback strappy versions to wear with...basically any outfit you can think of. Whenever you'd wear a black tee, swap it out with this.
Head-to-toe tonal is never a bad call, but this level of pink would be challenging for anyone but the master here. J. Lo's taking a super-challenging item of clothing—a slip dress in a light feminine color—and somehow not making it look twee.
(Faux) Furry Coats
The outerwear in the '90s/'00s had to be just as intense as the rest of your outfit. Voila: Britney Spears rocked this faux fur jacket when she received her star on the Hollywood Walk of Fame. More really is more!
And, yes, fauz fur has been getting better and better, but the key here is to go for a totally ridiculous color that looks wild no matter the season. May we suggest this jacket?
An Oversized Belt
Beyoncé hit the 2000s fashion trifecta during her appearance on MTV's TRL: low-rise cropped pirate pants with an oversized belt. Bonus points for that wallet chain. You could not have a more Y2K outfit, IMO.
You'll wanna match your belt to the cut of your jeans: I love an oversized belt with my high-waisted denim, as it accentuates my figure. But, since low-rise is coming back (sigh), you can also choose an option with a cool design.
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 hot summer dresses.
Baggy Joggers (aka Pirate Pants)
Did we all seriously think this was a flattering cut? No surprise, Gwen is wearing everything everywhere all at once, but the longer, baggier version is an item we're seeing everywhere.
Maybe skip the pattern, go monochrome, and drop it to floor-length–but keep the bagginess and and pair it with more structured pieces. I own this Amazon pair, and it's actually the most comfortable thing in the world.
We'll get to tracksuits in just a sec, but the whole ironic sunglasses at night was a fave of '90s/'00s stars. Honestly, J. Lo could be headed to the gym, a party, a brunch, or all three.
Dresses Over Pants
The look was to wear your jeans extra long so that they covered most of your shoe, even dragging on the ground a little behind you. The trend was big with teen actresses, as it allowed them to wear mini dresses while still looking family-friendly.
These days, I wouldn't necessarily say jeans under dresses is the look (although I've been proven wrong before)—it's more about subtle flared black pants or leggings that complement whatever you've got over it. This is one of those "needs tweaks before you can wear it IRL" trends.
It's that totally incongruous—is it winter? but also summer because of the flip-flops?—vibe that makes me LOL here. We used to go in for random scarves, so the key is to make it look a little more like part of the whole outfit.
Opt for something a smidge thinner and a shinier material that'll go with a button-down—almost like a chicer version of a tie—and you'll feel polished and hot, instead of "dressed like my neck is cold and the rest of me is fine."
Remember when these were just, like, sooooo fancy and sophisticated? The whimsical style paired perfectly with a chandelier earring and a half-updo at the time, although now it might read a bit "fairy princess goes to her prom."
If you wanna go asymmetric with your hemline now, pick options that feel just *a smidge* more high fashion: ruching and layers, yes, see-through and bunching, no.
Juicy Couture Tracksuits
Britney Spears in her Juicy Couture tracksuit was more than just a trend, it defined the style of a decade. The only thing that's missing is her Starbucks frappuccino.
So many unnecessary pockets. But truly, cargo pants had a big impact on fashion in the 2000s. And they have been back with a vengeance, with slightly less bagginess, a higher waist, fewer embellishments, and a streamlined look.
Nab yourself a pair and then wear it everywhere for years—honestly, they're so comfortable you'll never take them off. Opt for a pointed shoe, like Kate does here, to make it look like you actually have feet.
The Shipwrecked Look
Rags tied together with other rags, but make it expensive as hell. I like the peasant look Britney Spears is rocking here, and then she adds in the shipwrecked look with a half-ripped sweater. It won't be the first time it looks like Britney's stylist went wild with a pair of scissors.
Truly, follow your bliss, but sweaters that are ~artfully~ ripped these days look a little less moth-eaten and a little more "I meant to dress this way, promise."
The only thing we understand about this trend was that it was perfect for showing off your sick belly button jewelry. And also that Lindsay was the master of this look (I don't make the rules!!).
When in doubt, get yourself a lil cardigan that ties at the top and hangs open underneath. This lilac bb, this pretty red and pink option, and this double-tie guy feel trendy without feeling *too trendy*.
Short Shorts With Heels
The companion to the miniskirt is the short short pair of shorts that felt like you couldn't sit down in them. Then the hot, expensive, high high heels, because contrast! (Actually I think this looks pretty fun, if we swap out the top.)
I still like to be able to wear shorts that allow me to move around without flashing people, but plenty(!) of options are even shorter than that. The shoes, really, are the big investment, so make sure you like 'em before you buy.
Starlets, like Pink here, used to look like they raided their own jewelry boxes, liked everything, and wore it all at the same time. The only reason this works at all is the matching belt and (relatively) simple feel to the rest of it.
These days, you'll wanna focus on the short chain necklace first, and layer effectively with pieces that pair well. It's not about making a bird's nest of metal, basically, but a slightly more "thoughtful" feel. Then go with matching Y2K earrings.
Lacy Slip Dresses
Everyone was obsessed with lacy slip dresses in the early aughts. Truth be told, they were pretty much just lingerie. Even when the trend is made to be more formal, like the dress J. Lo wore to the Paycheck premiere in 2003, all I can see is fancy lingerie.
Fortunately, your present-day lacy slip dress has ~a few more~ details that distinguish it from underwear—like cool colors and a slightly more structured fit. Even if it looks a lil like nightwear, that can still be fun.
You know the shape: Tight and form-fitting at the bust, then a-line down to the fingertips?? The babydoll is absolutely back—stars like Olivia Rodrigo are a huge fan—but Lindsay Lohan did it first. Don't forget it.
You might have to play around with style and shape (I myself like one that starts flaring at the waist, otherwise I look literally 10 years old) but this can work for different figures. American Eagle has a bunch of its classic styles revamped, if you're interested in going full '90s.
Red Leather Pants
Of course, Christina Aguilera wore bootcut red leather pants with a matching top. At the time, there was no such thing as too much red leather. And even though, yes, this is OTT, she was ahead of her time with the whole matching top and bottom.
If you're gonna go with statement leather (or, even better, the vegan option), Delia's has a cool vintage version. Or, get an investment pair and wear them for more than one season—they would look amazing with white boots and a tee.
Scissors, man. All you needed was a pair of sharp shears to achieve this pop star-approved look. It almost feels like Britney's stylist started with two full shirts and ended up with a lot of rips and one sleeve. Just sayin.
Nowadays, strap or tie tees are a little more...intentional, let's say, but it still keeps some of that "haphazard" vibe—like, oh, I didn't know you could wear your shirt like that but also it looks cool!
Flared, Ripped Jeans
Only Shakira could do a fake fur stole, enormous silver necklace, top with only two buttons done, and messy flares to complete the look. But isolating the bottom half, a ripped flare is actually one of the ways the '90s updated the '70s to look more grunge-sexy.
These days, the ripped flare jeans you'll find are high-waisted (PHEW) without any of that tie-up business to contend with. It's also just a *hint* of ripping instead a full-on falling-apart situation.
Queen Bey can obviously do no wrong, ever, but I will say that I don't fully understand her top here. No matter what, though, I dig her gold sock boots that would now work beautifully with straight-leg jeans and a black blazer.
Sock boots have been back for a bit now and, IMO, the comfiest versions are these sustainable options, which come in a longer ankle length too if that's what you need. But yes, of course, I found gold ones for you too.
Corsets as Tops
The form-fitting, figure-boosting top was a "shocking for its time" take on underwear as clothing. Perhaps some balance would work better if you're thinking about the trend; With the whole corset-and-lace-up-pants situation Xtina's rocking here, it's just an accident waiting to happen.
Decorated and Patchwork Denim
K cool, I actually feel like I can pull this one off! Baby Hilary here has green accents at the top of her (low-rise!) jeans and at the collar and elbows of her jacket—which actually feels fun even now.
Your patchwork denim jacket probably won't be quite so on the nose—some fun vintage designs, maybe a pin or two. Major plus: These are customizable to your ~vibes~.
Collarless Leather Jackets
Think of the collarless biker jacket as the more punk sister to the '90s schoolboy blazer. Of course, you do *not* need the incredibly abs demonstrated by Carmen Electra here, or the lower-than-low jeans.
Lucky for all of us, the modern moto jacket is looser, more casual, and a bit more effortless than the '90s version. It might be a lil harder to find a white jacket these days unless you swap out the leather with tweed or cotton, in case you want to channel Ms. Electra perfectly.
Silk Scarf Tops
Here, Sarah Michelle Gellar creates a one-shoulder top with a piece of fabric that's tied under her arm. It's called fashion, look it up! The silk-scarf-but-make-it-a-shirt is coming back, and my non-abs are pretty mad about it.
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