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The 50 Craziest, Most Cringe-Worthy Outfits Celebrities Wore In The Early 2000s

A look back at the very questionable decade of fashion.

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Jeans, Clothing, Denim, Fashion, Footwear, Textile, Headgear, Street fashion, Shorts, Trousers,
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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 velour 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.

1
Clothing, Jeans, Denim, Fashion, Headgear, Leg, Abdomen, Outerwear, Textile, Hat,
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Ultra low-rise patchwork jeans, a belly chain, a cropped top, and a denim newsboy hat—Christina Aguilera combined all the major trends of 2001 into one hard-to-forget look.

2
Clothing, Shoulder, Dress, Fashion, Blond, Strapless dress, Joint, Cocktail dress, Long hair, Leg,
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Tube tops and boho skirts were an unexpected combination that everyone including Cameron Diaz embraced.

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3
Denim, Jeans, Clothing, Fashion, Cowboy hat, Textile, Blond, Fun, Outerwear, Headgear,
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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.

4
Fashion, Fashion design, Carpet, Joint, Performance, Event, Costume, Flooring, Red carpet, Black hair,
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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 (though it's unclear what "it" was).

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5
Face, People, Hat, Social group, Denim, Crowd, Facial hair, Headgear, Fashion accessory, Fashion,
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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.

6
Clothing, Jeans, Fashion, Denim, Leg, Hat, T-shirt, Trunk, Abdomen, Flooring,
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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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7
Textile, Red, Outerwear, Style, Dress, Fashion model, Fashion, Blond, Fashion design, Leather,
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Proving there was never such thing as too much pleather, Jessica Simpson really went for it in a head-to-toe red hot look.

8
Abdomen, Jeans, Fashion, Trunk, Event, Denim, Waist, Navel, Hip,
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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.

9
Blue, Textile, Style, Electric blue, Fashion, Waist, Costume accessory, Costume, Abdomen, Trunk,
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Pulling together some of the biggest micro trends of 2001, this Mya outfit is the definition of "doing the most."

10
Clothing, Fashion model, Fashion, Shoulder, Event, Leg, Waist, Hip, Haute couture, Long hair,
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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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11
Face, Footwear, Human, Trousers, Event, Shoe, Red, Textile, Dress, Outerwear,
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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.

12
Clothing, Thigh, Leg, Hairstyle, Muscle, Fashion, Human leg, Blond, Denim, Navel,
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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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13
Brown, Human body, Shoulder, Textile, Joint, Human leg, Waist, Style, Fashion accessory, Thigh,
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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.

14
Clothing, Shoulder, Dress, Pink, Fashion model, Fashion, Hairstyle, Peach, Cocktail dress, Joint,
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J.Lo made the It item of the decade—a velour 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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15
Human leg, Flooring, Fashion accessory, Carpet, Fashion, Thigh, Knee, Blond, Fashion model, Foot,
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At a Crossroads premiere, Britney embraced color coordination to the max in a matching pale pink hat, ruffled dress, and knee-high boots.

16
Shoe, Fashion accessory, Fashion, Abdomen, Brassiere, Navel, Carpet, Trunk, Waist, Thigh,
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As Paris Hilton emerged on the scene, she brought with her the shipwrecked asymmetrical skirts, belly shirts, and an abundance of pink.

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17
Clothing, Fashion, Premiere, Dress, Headgear, Carpet, Hat, Event, Flooring, Fashion design,
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Fresh off her American Idol win, Kelly Clarkson frequented belted dresses over boot-cut jeans.

18
Clothing, Fashion, Pink, Footwear, Tights, Leg, T-shirt, Thigh, Leggings, Knee,
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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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19
Jeans, Denim, Clothing, Cobalt blue, Shopping, Electric blue, Fashion, Trousers, Textile, Outerwear,
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The signature 2000s look: a colorful velour tracksuit with a camisole, and It bag.

20
Clothing, Blond, Footwear, Pink, Fashion, Shoulder, Performance, Flooring, Carpet, Shoe,
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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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