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The Worst Early 2000s Fashion and Outfits

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When it comes to the decades of fashion’s past, it’s easy to get inspired by the elegant silhouettes of the ’50s, the platform shoes of the ’70s, or even the distinct denim of the ’90s. When it comes to the early 2000s, however, we’re a little less inclined to bring back the major trends of the decade. From ultra low-rise jeans and belly chains to velor tracksuits, dresses over pants, and Uggs paired with denim mini skirts, the aughts were a time of truly questionable trends. Led by the stylish A-list of the time—Britney Spears, Christina Aguilera, and even NSYNC to Paris Hilton, Nicole Richie and Lindsay Lohan—the 2000s were unlike any other time in fashion. Take a look back at the “trendy” celebrity outfits of the fashion era you forgot existed.

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Ultra low-rise patchwork jeans, a belly chain, a cropped top, and a denim newsboy hat—Christina Aguilera combined there the major trends of 2001 into a hard-to-forget look.

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Tube tops and combination boho skirts were an unexpected that everyone including Cameron Diaz embraced.

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Nobody could forget this iconic moment in fashion history. The It couple of the time went for full-on denim and blinged out accessories in a look that could only belong to the early 2000s.

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There’s a lot to unpack here but, metallic going out top, distressed low-rise jeans, and floor-length fur jacket all in one? Pink wasn’t afraid to go for it (although it’s unclear what “it” was).

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NSYNC served up some truly interesting boyband looks on the red carpet as well. With bandanas, colorful fedoras, and a whole lot of bad denim, “eclectic” was one way to describe their style.

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Gwen Stefani rocked boxers peeking out of low-rise jeans, trucker hats, and a nameplate belt all in one for a red carpet look all the cool girls wanted to copy.

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Proving there was never such a thing as too much pleather, Jessica Simpson really went for it in a head-to-toe red hot look.

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Queens of coordinating outfits, Destiny’s Child, embraced lace-up jeans, belly shirts, and rhinestone belts in looks that Beyoncé probably wouldn’t be caught dead in today.

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Pulling together some of the biggest micro trends of 2001, this Mya outfit is the definition of “doing the most.”

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A studded corset worn with white pants and a silver hip chain was the dream going out look in 2000, as proven by Denise Richards.

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Though this look (thankfully) never went mainstream, Björk’s infamous swan dress at the 2001 Oscars became one of the most buzzed-about fashion moments of the decade.

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When wearing anything but actual shirts as shirts was a thing, Xtina embraced the trend with a scarf “top” and an ultra-mini denim skirt. (Don’t forget the signature newsboy cap.)

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Let’s not forget the shipwrecked look whose pioneers were Tara Reid and Paris Hilton. The It girls brought their ripped skirts and baby tops to countless red carpets.

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J.Lo made the It item of the decade—a velor tracksuit—even more 2000s by rolling up the leg to show off her high heels and throwing on a newsboy cap.

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at to cross roads premiere, Britney embraced color coordination to the max in a matching pale pink hat, ruffled dress, and knee-high boots.

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As Paris Hilton emerged on the scene, she brought her the shipwrecked asymmetrical skirts, belly shirts, and an abundance of pink.

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fresh off her American Idol win, Kelly Clarkson frequented belted dresses over boot-cut jeans.

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When graphic tees ruled all, Christina Milian decided to pair her “Queen of the Universe” t-shirt with a pink mini skirt, pink fishnets, a wrist sweatband, and pointed toe boots because why not?

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The signature 2000s look: a colorful velor tracksuit with a camisole, and It bag.

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We all couldn’t get enough of ponchos in every color, pattern, and with fringed bottoms. Eve brought the look to the red carpet with a pair of denim capris and hobo bag, really cementing its status.

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Boot-cut jeans, stylish flats, and camisole-inspired tops? Mary-Kate and Ashley doubled the trends in coordinating outfits.

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Further embracing the shipwrecked skirt look, Paris Hilton hit the 2003 MTV Movie Awards showing off another major staple of the early aughts: the belly-button ring.

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Kelly Clarkson

denim-skirt? Check. Platform flip flops? Check. Belly shirt? Check. Just in case you needed a reminder as to why we chose Kelly Clarkson as our American Idol.

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Even if it wasn’t cold, wearing a scarf with your look was essential. Ashlee Simpson went for it with her silky camisole top, cropped trousers, and pink velvet boots.

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The resurgence of leg warmers hit around 2003 (as spotted on fashion icon Mischa Barton). Once reserved for workouts, the ’80s essential came back as a “fashion accessory” worn with flats and paired with mini skirts.

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In an outfit that many of us probably tried to recreate, Lindsay Lohan styled her faded boot-cut jeans with a corset top layered over a button-down. Bonus points for the cool, J.Lo-inspired shades.

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As Uggs became the must-have footwear choice, it only made sense to pair the winter boot with ultra-short denim skirts à la Nicole Richie.

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Bringing back the fedora, Britney stepped out in a ripped Page Six cropped top and mini skirt that let her diamond belly-button ring shine. And let’s not forget the printed Patricia Field leggings that were necessary to wear underneath.

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Booty shorts, rhinestone belts, and trucker hats, oh my.

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gwen Stefani

Gwen Stefani became the unofficial poster-child for cropped pirate pants and fishnets.

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