25 most popular fashion and beauty trends of the past 25 years

Yahoo 25

This story is part of a series to celebrate Yahoo’s 25th birthday. Thanks for joining us along this wild, wonderful ride.

Everything old is new again when it comes to fashion and beauty. In 1995, celebrities like Jennifer Aniston, Mariah Carey, Drew Barrymore and Janet Jackson were wearing high-waisted jeans, overalls, plaid shirts, crop tops, slip dresses and matching sets — and in 2020 they’re wearing the same items again. Over the past 25 years though, so much has changed and come and gone, from the epic rise (and eventual fall) of brands like Von Dutch and Ed Hardy to yoga pants and crocs, distinctly 2000s trends. Check out 25 of the most popular fashion and beauty looks Yahoo users have followed over the past quarter century.

Tracksuits

No other fashion trend summed up the early aughts like the tracksuit (sorry, baby-doll dresses), popularized by Paris Hilton, Jennifer Lopez, Kim Kardashian and Madonna. The brand of choice: Juicy Couture's sticky-velour and terry cloth sets. However, Snoop Dogg, Missy Elliot and Gwen Stefani were partial to the sportier version of the look from adidas.

Britney Spears, Paris Hilton, Madonna

Trucker hats

These foam and mesh hats have been around since the 1960s, back when they were given away for free at truck stops as promotional products for companies like Mountain Dew, Shell Oil and John Deere. In the late 1990s, trucker hats weren't just for drivers anymore as kids started wearing them ironically. It became a full-blown trend when Ashton Kutcher, who grew up in Iowa just down the road from the largest truck stop in the world, started punking people while sporting trucker hats. The trend ultimately died down, but never fully went away. Now, the most popular trucker hats are all red with the phrase, "Make America Great Again" on the front. 

Dennis Rodman, Ashton Kutcher, Gwen Stefani

Skinny jeans

It’s been a long and gender-bending road to modern-day skinny jeans, from the 17th century breeches favored by French royalty to the “drainpipe” jeans of 1960s Mod girls and the distressed leggings of the '80s punk-rock look. And now, despite always-changing denim leg sizes, it’s clear that skinny jeans — whether super-high-waisted, stretchy like jeggings or cropped to mid-thigh — are definitely here to stay.

Kate Middleton, Harry Styles, Ashley Graham

Yoga pants

While leggings have been a fashion staple since the 14th century (history shows men wore the tight style in Scotland for mostly military wear), thank lululemon for the trend’s current status as a style staple. In 1998, the Canada-based company introduced its nylon and Lycra blend form-fitting pants. Thanks to lululemon’s popularity, yoga pants broke boundaries and were worn outside of the studio by many, eventually leading to the women’s workout clothing revolution and the rise of athleisure, the blurring of lines between athletic and everyday clothes.

Reese Witherspoon, Hilary Duff, Jennifer Garner

Ugg boots

First worn in the 1980s by Southern California surfers who could slip on the cozy boots after hitting the waves, the UGG boot took off across the country as people fell in love with comfy shoe and its ties to West Coast cool. The sheepskin boots first appeared on Oprah’s Favorite Things list in 2000, and from there, on the feet of countless celebrities, from the cast of MTV’s Laguna Beach to Paris Hilton and Britney Spears. While not the most flattering, the furry footwear certainly hasn’t gone out of style.

Kelly Osbourne, Giselle Bunchen, Sarah Jessica Parker

Wristbands for causes

After Lance Armstrong survived cancer and made his miraculous return to the Tour de France, he launched Livestrong. In 2004, to raise funds and awareness, the charity partnered with Nike to create rubber yellow bracelets imprinted with the nonprofit's name. The accessory was a must-have for years, seen on celebrities, sports stars, politicians and more — until the fad’s downfall, which coincided with Armstrong’s doping charges. 

Livestrong bracelet

Grillz

Not many dental trends can claim to have inspired a hit rap song. In 2005, Nelly’s “Grillz” climbed the charts, marking a peak pop culture moment for the iced-out teeth guards popularized by hip-hop stars like Paul Wall, Flavor Flav and Lil Wayne. Beyoncé, Katy Perry and Madonna also flirted with the ortho craze, while swimmer Ryan Lochte went for the ultimate mouthful when he flashed a bedazzled American flag smile for the 2012 Olympics.

Nelly

Ed Hardy

Name a more iconic graphic T-shirt. We’ll wait. The tattoo artist took his bold designs and licensed his brand to rave reviews. A who’s who of stars in the early aughts were spotted out and about in their Ed Hardy skull and tiger prints, kicking off a trend as shoppers descended on stores looking for the latest design. But the brand, which was helmed by Christian Audigier of Von Dutch fame, saw its end as reality stars like Jon Gosselin and the cast of Jersey Shore stepped out in the looks. Hardy said the associations ruined the brand name, telling CNN in 2013 that “morons dehumanized it.”

Vinnie, Fergie and JC Chasez

Crocs

The world, after being introduced to Crocs by Scott Seamans, George Boedecker and Lyndon Hanson in 2002, has never quite been the same. The three friends, who were inspired by a foam clog made by a Canadian company, which they licensed to develop, wound up adding a heel strap, and the rest is footwear history. The colorful, synthetic-fiber clogs have since been embraced by celebs from Mario Batali to Whoopi Goldberg and derided by fashion critics as “heinous” and “ugly” —  and, bizarrely enough, welcomed on runways thanks to collaborations with Balenciaga, PLEASURES and Post Malone. Most recently, they’ve become part of the VSCO girl uniform, for better or worse.

Wall display of colorful crocs

Choker necklace

A fashion accessory that’s evolved with the times, the choker has been around for centuries. The close-fitting necklace has famously been worn by Princess Diana in 1994, Gwyneth Paltrow to the Academy Awards in 1999 and later by Paris Hilton in 2002. By transcending a single material, being worn as a leather strip or decorated with diamonds and pearls, the choker fails to ever go out of style.

Cameron Diaz, Princess Diana, Rihanna

Birkenstocks

The practical cork sandals were first introduced in the United States in the ‘60s, but became beloved in the 1990s, when young Gen Xer’s started wearing them en masse. (Sometimes even with socks! Quelle horreur!) They gradually  fell out of popular culture until 2014, when Celine creative director Phoebe Philo debuted them in her runway show. In 2018, the “ugly shoe” trend took off, and more than 25 million pairs of Birkenstocks were sold in one year. 

Whitney Port, Kendall Jenner,

Keds

In 2020, sneakers are irrevocably connected to the celebrities who wear them. But believe it or not, it’s Keds we have to thank. Founded in 1916, the American company not only originated the sneaker but adorned star-studded feet like Marilyn Monroe, Audrey Hepburn and Yoko Ono (at her wedding to John Lennon, nonetheless) before Nike was even a brand. By the mid-1980s, owing to their appearance on the feet of Jennifer Grey in the pivotal scene of Dirty Dancing, the shoes became a symbol of modern femininity and strength. Over time, the company has leaned into its feminist origins, nominating Taylor Swift as its global ambassador in 2015 and ensure women for years to come will be proudly claiming — in her words —  “you belong with me.”

Mischa Barton, Taylor Swift, Ciara

Big eyebrows

America’s obsession over big eyebrows rivals the ever-increasing size of the two strips of hair themselves. While skinny eyebrows exploded in popularity during the 1990s, the trend — much to the dismay of those who’d already groomed theirs into submission — was almost single-handedly reversed by model Cara Delevigne when she exploded onto the fashion scene in 2011. Her “power brows,” as they were dubbed, harkened back to the lush, unruly brows of female powerhouses past such as Brooke Shields, and sent a message that less, in this case, is not more.

Cara Delevigne

Scrunchies

Enjoying a youthful comeback within the past year thanks to the trend of VSCO girls stacking them up their arms at least three at a time, Scrunchies have enjoyed a decades-long history. Actually invented in the 1960s, the soft hair band was patented in 1986 by nightclub singer and pianist Rommy Revson, and it quickly became an ’80s icon — returning in recent years (despite shade from Carrie Bradshaw) thanks to embracers including J. Lo, Kim Kardashian, Hailey Bieber and Selena Gomez.

Bella Hadid, Hayley Baldwin

Skull print scarfs

In 2003, British fashion designer Alexander McQueen introduced black scarves covered in white skulls. Celebrities like Nicole Richie, Lindsay Lohan and the Olsen twins quickly became fans of the moribund printed accessory after its runway debut and the masses (and fast fashion producers) followed.

Kim Kardashian, Nicole Richie, Christina Aguilera

Halter tops

From dresses to swimsuits and even crop tops, the halter is one of the most celebrated styles of women’s clothing that never seems to go out. The backless style was made most famous by Marilyn Monroe in 1955 when she wore a white halter dress that caught the breeze of a New York City subway. Since then, it’s been worn in various ways by numerous celebrities from the beach to the red carpet.

Vanessa Hudgens, Britney Spears, Victoria Beckham

Rachel haircut

So no one told you we’d all spend the mid-to-late-’90s with layered locks cupping the sides of our faces like hairy apostrophes. Though not even “Rachel” (Jennifer Aniston) had the choppy ‘do in the 1994 Friends pilot, the show’s success and a few strategic snips from hairstylist Chris McMillan ultimately made the look more popular than a meatball sub at Chez Tribbiani. 

Jennifer Aniston as Rachel Green

Frosted tips

Frosted tips If the signature sound of late ‘90s pop was the Backstreet Boys and *NSYNC, the signature hair was frosted tips. Best exemplified by Justin Timberlake’s curly dyed ‘do, everyone from Sugar Ray frontman Mark McGrath to 98 Degrees’ Nick Lachey had their hair strategically bleached blonde on top. While the trend thankfully died out as we ushered in the millennium, there were still a few holdouts – we’re looking at you, Guy Fieri. Still, versions of th style began to make a comeback in the past few years thanks to stars like Zayn Malik, Kristen Stewart and Pete Davidson.

NSYNC

Eminem haircut

People had been dyeing and bleaching their hair for decades before 1999 — but then Eminem introduced himself to the world as Slim Shady. Over the next few years, so many teenage boys and young men bleached their hair, it was hard to tell who was the real Slim Shady. Even though Eminem has gone back to his natural brunette hair these days, the trend is still alive, with celebs like Adam Levine recently rocking that platinum peroxide look.

Eminem

Ombre

Like most trends, ombré started with Britney Spears in 2000 when she first dyed her hair in a subtle fade from dark roots to light tips. Likely inspired by the ‘90s trend of frosted tips (donned by Spears’s former beau Justin Timberlake), ombré was popularized by a number of celebrities from Aaliyah and Beyoncé to the Kardashians. But it didn’t stop at hair. Instead, the shading effect found its way onto nails and makeup, and even infiltrated the home as Martha Stewart noted it as a useful trend for home decor. Today, ombré can be seen everywhere — from the salon to a bakery filled with ombré frosted cakes. Safe to say the transitional color trend is here to stay.

Bella Thorne, Khloe Kardashian, Drew Barrymore

Man buns

Men rocking long hair is not a new beauty trend, but when they started tying their tresses back on the tops of their heads with elastics, people began to take notice. Spotted in U.S. hipster enclaves like Brooklyn, N.Y. and neighborhoods in Los Angeles, the trend then spread among celebrities like Leonardo DiCaprio and Jared Leto. It also encouraged a wash of new hairstyles for men, who could grow out their close-crop cuts to wear their hair atop their heads, accessorizing with a beard, or perhaps an undercut to show off a shaved back-of-head. 

Jason Momoa and Jared Leto

Nail art

Nail art has long been a way for men and women alike to make their claws a fashionable accessory. From the French-painted tips displayed by the ladies on MTV’s Laguna Beach, to the eccentric styles donned by the Kardashian-Jenners and Cardi B, the designs that decorate a person’s nails have garnered lots of attention over the years. So much so that nail art trends have been tracked through today’s biggest social media platforms — from Pinterest and Tumblr to Instagram and now TikTok. TNT even developed the show Claws, which takes place in a nail salon and pays close attention to the nail art defining ever-evolving beauty standards.

Cardi B

Unicorn everything

You couldn’t escape unicorns in 2017: Starbucks introduced the Unicorn Frappucino; hair salons were dyeing (human) manes every shade of the rainbow; Lisa Frank made a comeback; ROYGBV-themed makeup took over the cosmetics landscape; and unicorn headbands, costumes, skirts, towels, and more colorful items hit shelves. The mythical animal theme was so prolific that publications like Fast Company, Refinery29 and The Guardian even waxing poetic about the creature’s popularity, with Vox explaining society’s love by writing that “of all the things people remember from childhood, perhaps many are finding a new fondness for unicorns because they are imaginary, ridiculous, fantastic, and a perfect escape from the confusing times of today.”

Float, Starbucks Frap, Katy Perry

Fake tanning

The dangers of ultraviolet rays (skin damage and cancer) are known in 2020, but tanning has a style history. Some attribute French clothing designer Coco Chanel to starting the obsession after being photographed during vacation. Cue the sale of oils, powder and cream to induce the bronze, followed by the first indoor-tanning bed and the popularity of "sunless" sprays in the early aughts. Today, many states ban in-door tanning for minors, sunbathing is cautionary and beauty standards have welcomed a more natural complexion.

Jersey Shore

Harry Styles haircut

It’s fitting that a guy named Harry Styles would launch a hairstyle craze, but the former One Directioner and his bouncy brown moptop did indeed succeed Hugh Grant as the world’s reigning British man with fabulous floppy hair everyone wants. While Styles’s current shorter ‘do — now paired with frilly blouses and candy-colored Thin White Duke-style suits in the post-boy band era — no longer falls to his shoulders, his curls remain worthy of a conditioner commercial. 

Harry Styles