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15 Of The Most Memorable 2000s Fashion Trends, Explained

It’s a common belief that when it comes to modern fashion, trends live on a 20-year-cycle. If that assumption holds true, then the 2020s are set to repeat much of the fashion that dominated the 2000s.

It’s already happening, actually. From cargo pants to thong sandals, fashion is making a significant retrograde to the early aughts. Some might not be ready for it. For all the excitement about square-toed sandals, there’s also dread for the return of some of the decade’s more perplexing trends.

Below, a look at 15 of the most unique, memorable, decade-defining fashion trends from the 2000s, for better or worse — and a few clues on which ones might be on their way back (if they’re not already).

1. Dresses over jeans

A fan favorite in lists of the worst fashion trends of the decade, the dress-over-denim look was at the time considered an advanced styling move for those who appreciated it. It was also seen as an avant-garde, literal extension of the going-out top.

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Justin Timberlake and Britney Spears at the premiere of “Crossroads” in 2002. The pop star is wearing a dress over denim with matching knee boots and newsboy cap — a summary of many of the most definitive 2000s trends.
CREDIT: Splash

2. Going out tops

What defines a “going out top”? Usually, there was a halter situation, or a strapless neckline. Often, there were sequins, or chiffon flourishes, or at least a turquoise hue or bright white (the better to show off a fake tan) done in a jersey material. In the early aughts, there was nearly no other option for evening wear than the going out top, paired with low-rise jeans and a pair of pointy-toed pumps or strappy sandals.

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Jennifer Love Hewitt at the Nickelodeon Kids Choice Awards in 2004.
CREDIT: Splash

3. Low-rise jeans — and the whale tails that came with them

One begat the other. Low rise jeans and G-string thongs were often displayed simultaneously, intentionally or unintentionally. Both trends have already begun their comeback as an intentional, somewhat ironic look, worn on the likes of Bella Hadid and Hailey Bieber.

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Carmen Electra in 2002, wearing low-rise jeans, which were often pair — intentionally or unintentionally — with G-string or thong underwear.
CREDIT: Mega

4. Uggs-and-miniskirts

Oprah may have introduced most of the U.S. to Ugg’s shearling boots, but it was the likes of Paris Hilton, Nicole Richie and Lindsay Lohan who introduced a younger generation to the ways in which the footwear would be styled. The more fashion-forward option was Ugg’s classic boot in the tall option, iconically and ubiquitously worn with an Abercrombie & Fitch denim miniskirt (in an ultra-high hemline). As Ugg boots continued their comeback in the age of the pandemic, the styling combo could make a comeback, especially with Gen Zers.

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Lily Allen in 2008 wearing denim shorts and Ugg boots.
CREDIT: Mega

5. Capri pants

Somewhere along the way, fashion decided that cropped pants were a desirable and flattering silhouette, even though they were neither for most of its wearers. Originally picked up as a retro-inspired style, the pant quickly established its own identity in the aughts — one that continues to reverberate through the fashion of the masses today (as parodied in the upcoming “Barb and Star Go to Vista Del Mar”).

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Jennifer Lopez at the Nickelodeon Kids Choice Awards in 2004.
CREDIT: Splash

6. Big belts

Often a forgotten or overlooked accessory, the belt had one of its biggest moments in the 2000s — literally. Thick and equally substantial in its hardware, the wide belt was a permanent fixture of the decade, even if it moved around a bit on the waist:  In the early half, they were worn lower, slung around the hips. In the later years, they were worn squarely and tightly along the higher natural waistline.

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Paris Hilton and Kim Kardashian in 2006.
CREDIT: Splash

7. The gladiator/T-strap/cutout sandal-bootie

There were many footwear trends to come out of the decade, but one of the most original was the cutout bootie-sandal. A hybrid style, the shoe was a Frankenstein of sorts that started with the strappy sandal morphing into a chunkier version of itself: straps became thicker until they became more of cutouts, while the heels went from stiletto to cone or stacked styles.

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CREDIT: Mega

8. Babydoll dresses

From trapeze frocks to sacks and empire waists, the higher waistline of dresses (in any hemline, from mini to maxi) dominated the aughts. The silhouette has already made a comeback in this decade, in the ethereal, child-like pieces from designers like Cecilie Bahnsen.

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Halle Berry at the premiere of “Catwoman” in L.A., 2004.
CREDIT: AP Images

9. Menswear vests

A nod to the classic rock and punk scene of past decades, the button-up, menswear-inspired vest was a late-aughts antidote to the babydoll dresses and bubble hems of the time — though equally as much of a schtick in its own right.

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Rihanna in London, 2007, wearing a vest and newsboy cap (and a boot, after injuring her ankle).
CREDIT: Mega

10. Flip-flops as real shoes

An evolution of the platform slides and thong sandals of the late ’90s, the classic flat flip-flop was worn as a real shoe in the 2000s. Today the sandals costs no more than $26 for a pair of Haivianas (the top of the line on flip-flops), and they were even cheaper then — and yet, celebrities who could afford much more expensive footwear still opted for the shoes on a regular basis.

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Vanessa Hudgens with Zac Efron in New York, 2007, wearing flip flops while shopping.
CREDIT: Mega

11. Bubble hems

Both retro and futuristic in silhouette, the bubble hem was a simple garment technique that produced a definitive look in the late 2000s. Most often worn with platform, peep-toe pumps or cut-out sandal-booties.

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Lauren Conrad at the 2008 MTV Video Music Awards in a bubble hem dress.
CREDIT: Mega

12. Platform pumps

At the end of the decade, the higher the shoe, the better — which is basically how it went at the beginning of the decade (one might even develop a theory of the 10-year-cycle for the platform). They came in peep toes or round almond shapes and were worn with bubble hems, sack dresses and the skinny denim that was just starting to take hold at the time.

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Kristin Cavallari in a pair of platform peep-toe pumps in Las Vegas, 2008.
CREDIT: Splash

13. White tank tops

Yes, they were called “wife beaters” without the blink of a politically correct eye. The ribbed men’s undershirts from the likes of Hanes, Fruit of the Loom (drugstore varieties were the most authentic options) read as subversive at the time, an answer to all of those girly babydoll dresses, platforms and going out tops.

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Avril Lavigne at the 2002 MTV Video Music Award.
CREDIT: Splash

14. Cropped jackets and shrugs

Lest a going-out top or babydoll dress appeared too risqué, there was always a cropped cardigan or jacket to temper the mood. Usually embellished, like everything else in the decade, the knitwear was mostly done in synthetic blends but also in more natural crocheted yarns.

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Miley Cyrus performing in L.A., 2008.
CREDIT: Mega

15. Long peasant skirts

A somewhat forgotten trend in the canon of 2000s fashion, the maxi “peasant” skirt (known called a tiered skirt, for obvious reasons was actually a very integral piece in the 2000s-era closet of many. It was often accessorized with a plethora of other trends from this list, including (but not limited to): wide hip belts, tank tops, cropped cardigans and — yes — flip flops.

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A pregnant Britney Spears with sister Jamie Lynn in L.A., 2005.
CREDIT: Mega
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