20 Major Fashion Trends of the Past 20 Years

In the new millennium, fashion took a turn toward the maximalist. The early to mid-1990s had down-to-earth grunge looks and severely chic minimalism, but by later in the decade and into the early aughts the sparkly, candy-colored fashions of pop stars like The Spice Girls and Britney Spears started to filter into contemporary teen style. In these innocent years before social media influencers became style guides, the fashion-obsessed masses took cues from magazines and celebrities. As is so often the case in fashion, a lot of these trends (many of which—let’s be real—weren’t that cute to begin with) are now coming back in style, especially among Gen Z-ers who weren’t even born when the looks first trended.

While we may not want to squirm back into a pair of low-rise jeans anytime soon, it’s still fun to reflect on some of the chaotic but occasionally cute trends that defined the 2000s. Here are 20 of them.

1. Juicy Couture Tracksuits

Velour Juicy Couture tracksuits, with their signature J-shaped zippers and form-fitting-yet-comfortable cuts, were the unofficial uniform of “off-duty” celebrities and high school mean girls alike. Before brands like Lululemon and Outdoor Voices came to represent athleisure in the social media age, Juicy Couture defined the idea of leisurewear as a status item, making matching hoodies and sweatpants seem chic rather than dowdy through the power of celebrity branding and a high price tag.

2. Trucker Hats

Truck drivers may seem like an unlikely source of fashion inspiration, but the aughts were a strange time. For a brief but unforgettable period, trucker hats—often emblazoned with cutesy phrases like “Drama Queen” or the logo of then-omnipresent brand Von Dutch—could be spotted on the heads of many celebrities. These mesh-lined baseball caps embodied the era’s obsession with high/low styling, appropriating an accessory often associated with blue collar workers in the name of trendiness.

3. Low-Rise Jeans

Whether embellished with rhinestones, intentionally distressed, bootcut, or worn head-to-toe (thanks, Britney and Justin), denim was truly doing the most in the 2000s. The most prevalent denim abomination of the time was unquestionably low-rise jeans. In an era when washboard abs were presented as the height of sex appeal, perilously low-rise jeans (sometimes paired with visible thong underwear if you were feeling particularly spicy) became the dominant form of denim, making a garment often worn for casual comfort into something more bold and ready to be shown off.

4. Miniskirts

Miniskirts have been a fashion staple since first gaining popularity in the ’60s, but they became more mini than ever in the 2000s. Denim miniskirts, often looking like a perilously small rectangle, were commonplace. Many of the common miniskirt silhouettes at the time included ruffled edges referred to as bubble hems. Some of these micro-minis were cute and flirtatious—but you just had to be careful to not drop your keys, lest you reveal too much.

5. Butterfly Clips

A lot of early ’00s fashion trends were holdovers from the late ’90s, and butterfly clips were no exception. These dainty, butterfly-shaped clips may not have been the most practical, seeing as they barely held any hair in their colorful plastic claws, but they added a whimsical touch of femininity to any look, and served as the ideal complement to the updos that were popular at the time.

6. Crop Tops

If you were going to wear some stylish low-rise jeans or a miniskirt, there’s a good chance you’d be topping it off with a crop top. These belly-revealing shirts, also known as baby tees, came in a variety of fabrics and colors (some were even “popcorn shirts” made of weird, ultra-stretchy fabric), and could look sweet or edgy depending on how they were styled. Later in the decade, American Apparel pushed a hipper, more minimal kind of crop top, and in recent years the shirts have become a common sight at teen-favorite shops like Brandy Melville.

7. Flip Flops

It’s a wonder that more women weren’t constantly injuring their ankles, given how popular flip flops were in the aughts. These simple sandals, which are really best suited to the beach, became an everyday staple, often paired with capris or a minidress. Traditional flip flops were in style, but the emblematic pairs of the time sported heels or chunky platforms, convincing a generation of women to fool themselves into thinking a strap awkwardly wedged between the toes was both comfortable and stylish.

8. Ugg Boots

Squishy and shearling trimmed, Ugg boots looked better suited to a ski lodge than a paparazzi shot, but the Australian brand became an unlikely ’00s icon. The boots were comfortable and able to be worn without socks, giving them a grab-and-go vibe that was highly versatile. Uggs may not have been the cutest boots, but their slightly homely yet chic look, expensive-but-not-outrageous price tag, and carefree vibe made them a status item.

9. Dresses Over Pants

Unsure whether you want to wear a dress or a pair of pants? Back in the ’00s, you could wear both at the same time. This unholy pairing, which showed up on a surprising number of red carpets, sought to mix the casual and the cutesy. A dress over jeans said you were girly enough to wear a dress but edgy enough to pair it with something unexpected. The end result may have been awkward, but hey, it’s the thought that counts.

10. Logomania

Logos were everywhere in the aughts. They could be found plastered on T-shirts, sneakers, bags, and even the rears of shorts and sweatpants. Before there was social media, branding oneself often came from dressing like a walking billboard. Designer logos for high-fashion houses like Chanel, Dior, and Fendi were sought-after (and frequently knocked-off) status symbols—and perfectly symbolized the excesses of pop culture at the time—while logos for streetwear brands like Baby Phat and FUBU became synonymous with the mainstreaming of hip-hop style.

11. Cargo Pants

With their baggy shape and abundance of pockets, cargo pants aren’t exactly known for being flattering, but they were a tomboyish essential in the ’00s, often paired with a tank top for maximum casual cuteness. The popularity of these pants may have had something to do with the patriotic, militaristic national mood that permeated the culture. Or maybe they were just more comfortable than those pesky low-rise jeans that were so popular.

12. Designer Purses

In a period obsessed with status and branding, “It” bags carried by the rich and famous became the ultimate mark of a fashionista. While the luxury design houses that produced these bags had been around for decades, their accessories gained wider recognition thanks to fashion-conscious shows like Sex and the City and Gossip Girl. Playful designer collaborations like Stephen Sprouse’s and Takashi Murakami’s Louis Vuitton bags broadened the appeal of a legacy brand with pop imagery, and bags by Balenciaga, Chloé, and Dior, among others, were draped on the arms of many a starlet.

13. Rhinestone Embellishments

Practically anything that could be worn in the aughts could be bedazzled. Tops, jeans, shoes, even cellphones—all were fair game for rhinestone embellishments. The sparkle of a rhinestone on an otherwise casual garment instantly elevated it to camp status. Rhinestones are totally unsubtle and proudly fake, and that’s what made them the official gem of the era.

14. “Going-Out” Tops

Any top can be a going-out top if you want, but the going-out tops of the 2000s have a particular look that’s unmistakably of the time. The classic going-out top was often drapey, decked with sparkles, and inevitably paired with low-rise bootcut jeans. These tops conveyed the message of being down to party but not so precious about it that you’re going to put on a dress, and were frequently available at a burgeoning array of fast fashion retailers.

15. Skinny Scarves

Whether tied around one’s neck or over a tunic or pair of pants as a makeshift belt, the skinny scarf was a staple. These scarves gave any outfit a touch of hip je ne sais quoi. They were a simple, easy-to-wear but passably stylish accessory that could look hipster, boho, or emo, depending on the rest of the outfit.

16. Ed Hardy Tattoo Prints

As tattoos became more and more commonplace, so too did tattoo-print clothing. Ed Hardy shirts and caps, featuring garish images of iconic tattoos, were a must-have for the reality stars of the day. Ed Hardy designs embodied hard-partying bro energy, with a vibe that suggested you were tough enough to rock tattoo imagery but still cared about brand names.

17. Graphic Tees

“PRINCESS,” “BABE,” “QUEEN OF THE UNIVERSE”—these were just a few of the many appellations splashed across T-shirts in the 2000s. These sassy tops pedaled a simplistic branded version of girl power, with an early-meme-like directness. Celebrities like Paris Hilton, Lindsay Lohan, and Britney Spears often wore graphic tees as a means of winking at their tabloid personas, and were spotted in shirts reading “STOP BEING DESPERATE,” “SKINNY BITCH,” and “DUMP HIM,” respectively. That’s certainly one way to make a statement.

18. Tinted Sunglasses

Sunglasses in the ’00s were more often worn to look cool than to protect one’s eyes from the sun. Aviator sunglasses with pale tinted lenses (often in shades of brown or pink) were a must-have accessory that added a diva vibe to any outfit. While dark sunglasses are invariably better for your eyes, tinted ones at least have the benefit of making you look like you just stepped out of a music video.

19. Shrugs

Was it a sweater? A vest? A glorified scarf? The shrunken shoulder coverings known as shrugs were some of the most confusing garments of the aughts. At a time when there was no such thing as too many accessories, it made perfect sense that an article of clothing as seemingly frivolous as the shrug would come into fashion.

20. Fedoras

Oh, fedoras. The classic hat was so cool in the Old Hollywood era but became so cringey decades later. Worn by men and women alike, the fedora of the 2000s often topped off a gaudy outfit with a rigid brim worn at a jaunty angle. These fedoras didn’t have the understated suavity they did in earlier decades, but rather felt like one more exaggerated accessory in an era that was positively full of them.