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Best & Worst of 2000s Fashion Trends

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Ahhh, the 2000s. Never has a decade seemed so close, yet so far away. We still know all the words to Survivor by Destiny’s Child, but a hot pink phone that flips open seems pretty archaic.

Fashion trends of the 2000s hit us the same way. Some of those trends seem so relevant even today. And others, not so much. Here’s a look back at some of the best and worst of the decade.

The Best Fashion Trends of the 2000s

1. Yoga Pants

Did we ever live in a world in which loungewear was not acceptable? Of course, it’s no excuse to look sloppy — but having the option to wear yoga pants in lieu of a pair of sweatpants or leggings added a decidedly interesting twist to casual ensembles everywhere.

Yoga pants essentially became the pants du jour by the middle of the decade, and it seemed like everyone had at least a pair. Not surprisingly, that still holds true today.

2. Ballet Flats

The mid-2000s also saw the return of the always beloved ballet flat. What was once too prim and proper for the modern-day woman suddenly became a mainstay — the one pair we can turn to in moments of great pain caused by unbelievably torturous heels that weren’t practical for anything, really.

Ballet flats felt charming, sweet, and smart all at once, and fit nicely into both professional and off-duty wardrobes.

3. Military Styles

Military influence soared towards the decade’s end, when there was a brief departure from the peppy, poppy styles that reigned in previous years. The military look was more stern, crisp, and no-fuss with a fashion-forward twist — thanks to beautiful detailing that set each piece apart from anything else in the closet.

Jackets were accented by bold buttons, cavalier boots suddenly became everyday sightings, and smart trousers were essential.

4. Gladiator Sandals

Who would have thought the gladiator sandal would still be around after all this time? It felt like a dubious trend when it first turned heads back in the late 2000s. It was too strappy and too complicated-looking to really make sense in a basic wardrobe.

Yet here we are today, wearing them with great enthusiasm to everything from Sunday brunches to house viewings. The gladiator sandal is a comfortable alternative to a ballet flat and adds a little sparkle to a dress.

The Worst Fashion Trends of the 2000s

1. Low-Rise Jeans

Low-rise jeans were a carryover from the previous decade, when teen startlets like Britney Spears and Christina Aguilera made them a novelty for tweens and teens. And then, sadly, 20-somethings and up embraced the look, too.

beyonce 1
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The downside of the low-rise? They were, er, a bit too low at times. So low that you had to pause and consider the safety of bending over to pick up the pen you dropped. You’d recognize that doing so would display your backside crack — but you’d bend over anyway because you needed your pen back. Then you’d have to give a little tug to move your jeans back to the right place.

That’s way, way too much work. Good riddance to the low-rise.

2. Tube Tops

Another leftover from the previous decade, tube tops experienced a mini revival in the middle of the 2000s. They often showed up as a convenient partner for a pair of flared pants.

Cameron Diaz wearing a tube top
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But the tube top fizzled quickly. It wasn’t quite versatile enough for daily wear. And, it didn’t hold the same appeal as, say, a cropped sweater or jacket. You can still spot them on the occasional celeb, though.

3. Trucker Hats

Pink Von Dutch hat
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In the 2000s, we saw both men and women don trucker hats as if they were mandatory. The look has true meaning in punk and skater cultures, but in the mainstream it felt forced and unnatural — especially when it turned up on the likes of Madonna, Justin Timberlake, and Lindsay Lohan.  

4. Too-Short Capri Pants

To varying degrees, capri pants are a classic that peeks into the trend scene now and again. Truth be told, there will always be a way to wear cropped pants with style — in the right length and shape, they happen to look amazing with pumps and a smart top.

Denim capri pants with embellished pockets
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The 2000s interpretation of capris wasn’t quite so refined. We saw the length shorten to just below the knee, and the cuts were bulky and unflattering. To make things worse, the likes of JLo and Rihanna showed up sporting cargo versions with quirky, belly-baring tops and knee-high boots. It was all kinds of wrong.