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This October marks Who What Wear’s 20th anniversary. For two decades, we’ve reported on trends, created shoppable guides, and covered celebrity style. To celebrate our birthday, we’re taking a nostalgic look at the past 20 years of fashion trends.
Going back to the iconic year 2006, when Who What Wear began, Paris Hilton, Nicole Richie, Britney Spears, and Lindsay Lohan were all over paparazzi shots. It’s also the year She’s the Man and John Tucker Must Die came out, Hannah Montana premiered, and Daniel Powter’s “Bad Day” was playing on repeat on the radio. It was a time of Lancôme Juicy Tubes, Nars Orgasm blush, and Juicy Couture Eau de Parfum thrown into purses next to a pink Motorola Razr, Sidekick, or BlackBerry. We loved Pinkberry and Jamba Juice and were somehow getting around using printouts from MapQuest. Running until 2009, this era is often referred to as the mid- to late aughts and is considered to be a golden age of fashion. It was all about low-rise skinny jeans, oversize sunglasses, velour tracksuits, baby-doll tops, and denim miniskirts. And then there were all the Balenciaga City bags, Von Dutch trucker hats, gladiator sandals, bandage dresses, bubble hems, shrugs, waterfall cardigans, ruffles, cropped jackets, wedges, deep V-necks, gauchos, fitted vests, and sequins… And as iconic as it was, there are still a few trends we’d like to pretend never happened: headbands worn across the forehead?!
Moving into 2010 through 2014, Instagram, Snapchat, and Vine each launched, and Tumblr was still going strong. We often look back and wonder, What were we thinking? Aesthetics like twee, festival fashion, and normcore—along with trends such as peplum tops, statement necklaces, flared skater skirts, platform ankle boots, high-waisted jeans—were the go-tos. And who can forget the infinity scarves, riding boots, maxi dresses, flannel shirts, crop tops, and Chelsea boots. Then, from 2015 to 2019, model-off-duty style was in, led by Kendall Jenner, Kim Kardashian, Gigi and Bella Hadid, Hailey Bieber, and Emily Ratajkowski. Fashion people were carrying Baguette bags and wearing bike shorts, straight-leg jeans, bodysuits, puffer coats, blazers, bucket hats, tiny sunglasses, tailored suits, cutouts, and lug-sole boots. The term “millennial pink” came to be, and so did King Kylie.
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More recently, trends started moving differently. TikTok and its micro-trends changed how style spreads. Buzzwords like quiet luxury, ’90s minimalism, clean girl, balletcore, and the Y2K revival all had their moments from 2020 until now. Jelly flats, once a childhood favorite, came back, alongside knee-high boots, faux-fur coats, barrel-leg jeans, east-west bags, Mary Janes, and track pants. Skirt lengths shifted from mini to knee-length. And Hailey Bieber and Kendall Jenner remain style icons, alongside tastemakers such as Devon Lee Carlson, Zoë Kravitz, Zendaya, Gabbriette, Dua Lipa, and Sofia Richie Grainge.
While some things have changed since 2006—many of us will never be caught in skinny jeans again—others stayed the same: Oversize sunglasses are back. Ahead, 20 trends that defined the past 20 years.
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1.
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Kate Moss was the poster child for low-rise skinny jeans, as seen in her 2008 Glastonbury outfit worn with classic black Hunter Wellington boots as Kings of Leon, Amy Winehouse, James Blunt, and more played the three-day festival. It was hard to escape the polarizing silhouette during this time—it was the denim trend.
BDG
Skylar Low-Rise Skinny Jeans
2.
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When I think of oversize sunglasses, my mind goes straight to Nicole Richie and Paris Hilton—from Chanel’s Shield to Tom Ford’s Whitney. Now, they’re back as the top sunglasses trend of 2026, with Khaite x Oliver Peoples’s 1967C as the most-wanted pair.
3.
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Velour tracksuits, such as the iconic hot-pink Juicy Couture set, were everywhere. Mariah Carey even one-upped hers by doubling up on trends and wearing a capri version.
Juicy Couture
Og Big Bling Velour Track Pants
4.
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I did a double take when I came across this photo of Rihanna wearing a baby-doll top. It really was a different time—which leads us to our next trend…
Hollister
Ruffle Trim Tunic Babydoll Top
5.
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…denim miniskirts—especially ones from Hollister and Abercrombie. I remember the outfit formula being a baby-doll top worn with a denim miniskirt and leggings underneath.
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6.
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If there’s one item I was most shocked to see return in 2026, it was peplum tops. The revival of this mid-2000s style surprisingly was on the runways, and celebrities like Taylor Swift and Millie Bobby Brown have both worn the divisive trend.
7.
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Statement necklaces were the most popular jewelry trend for years, like the J.Crew bubble necklace. That best-selling style was actually designed by former Creative Director (and The Real Housewives of New York City cast member) Jenna Lyons. Then came an inexplicable extension of the trend: owl necklaces… You may think of Zooey Deschanel, but Lady Gaga was actually ahead of her time wearing one back in 2005. I recommend a TikTok trip down memory lane.
eBay
J. Crew Bubble Statement Necklace
8.
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Flared skater skirts are a relic of the early 2010s. Though they originally went mainstream in the ’80s. Taking their name from figure skating outfits, these short, high-waisted A-line skirts were a staple at American Apparel, and everyone from Ashley Tisdale to Taylor Swift wore them.
Fleur du Mal
Knit Flared Mini Skirt
9.
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I’m not sure how people walked around in these, but platform ankle boots—and sometimes even open-toe pairs—were everywhere. Jeffrey Campbell’s Lita boots are hard to forget.
10.
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After years of being subjected to low-rise skinny jeans, high-waisted jeans were welcomed with open arms. Once we started wearing them, it was hard to remember a time when we lived without them.
Reformation
Bex Super Stretch High Rise Wide Leg Jeans
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11.
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Athleisure was a key part of the model-off-duty craze—from Emily Ratajkowski to Kendall Jenner—with brands like ALO and Lululemon at the forefront.
Alo Yoga
Alosoft High-Waist 7/8 Highlight Legging
12.
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Perhaps it started on the heels of the normcore aesthetic—which Merriam-Webster defines as “a style or category characterized by things that are purposely chosen for being ordinary, everyday, or unexceptional”—but dad sneakers became beloved by the most unlikely demographic: fashion people.
New Balance
Gender Inclusive 9060 Sneaker
13.
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This photo of Kendall Jenner and Gigi Hadid both wearing bomber jackets at the same time pretty much sums up their popularity. From L.A. to NYC, it was as if celebrities overnight started wearing orange-lined MA-1 fighter pilot bomber jackets from Alpha Industries.
Alpha Industries
Ma-1 Bomber Jacket
14.
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Ganni and Batsheva made the dress that embodied 2015 to 2019: prairie dresses. As the name suggests, these were inspired by the pioneer and Victorian eras, characterized by high necklines and puffy sleeves.
GANNI
Floral-Print Cut-Out Midi Dress
15.
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Baguette bags had their place in the early 2000s and are back for the Y2K revival, but they also resurfaced in 2019. Amanda Seyfried and Emma Roberts even attended Fendi’s Baguette Forever event that year, which commemorated the reedition of the house’s iconic 1997 Baguette bag.
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16.
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While previous years were defined by skinny, high-waisted, and straight-leg cuts, denim trends have now shifted to baggy jeans. Hailey Bieber, known for her understated style, wears them on repeat—even releasing a pair with Gap called The Hailey Jean, designed around the relaxed silhouettes she’s become known for.
Gap
Low Rise ’90s Loose Jeans
17.
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Low-profile sneakers have become the It shoes in recent years, such as 2025’s trending sneaker-ballet flat hybrid, the Puma Speedcat Ballet. Other viral pairs include Adidas’s Taekwondo and Tokyo styles, Onitsuka Tiger’s Mexico 66, and Nike’s Moon Shoe collaboration with Jacquemus. The style has even dominated the runways at Tory Burch, Dries Van Noten, Prada, and Miu Miu.
18.
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I was a capri skeptic for years, but it might actually be my favorite trend to emerge between 2020 and 2026. I was conflicted about the ’90s and early 2000s style at first, but my mind has changed. It’s the ideal piece when you want something comfortable with stretch and movement while still looking put-together—especially when paired with ballet flats or kitten-heel sandals.
SKIMS
Smooth Lounge Capri
19.
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Next, a controversial one: sheer pieces. From runways to street style and red carpets, this unexpected trend is an acquired taste—you probably either love it or hate it.
20.
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Another trend Bieber wears all the time is kitten-heel thong sandals, specifically her $560 Toteme pair—an elevated take on flip-flops.
Toteme
Leather Heeled Flip Flops
