From Denim Mini Skirts to Loose-Fitting Jeans: Two Decades of Fashion Trends

      This October marks the 20th anniversary of Who What Wear. For two decades, we have highlighted trends, crafted shoppable guides, and reported on celebrity fashion. In celebration of our milestone, we are nostalgically reflecting on the last 20 years of fashion trends.

      Returning to the landmark year of 2006, when Who What Wear was launched, celebrities like Paris Hilton, Nicole Richie, Britney Spears, and Lindsay Lohan dominated the paparazzi's lenses. This year also saw the releases of films like She's the Man and John Tucker Must Die, the debut of Hannah Montana, and the continuous play of Daniel Powter's "Bad Day" on the radio. It was a period filled with Lancôme Juicy Tubes, Nars Orgasm blush, and Juicy Couture Eau de Parfum tossed into bags alongside pink Motorola Razrs, Sidekicks, or BlackBerrys. We enjoyed Pinkberry and Jamba Juice, and navigated with printouts from MapQuest. Spanning until 2009, this era is frequently known as the mid- to late 2000s and is viewed as a golden age for fashion. The focus was on low-rise skinny jeans, oversized sunglasses, velour tracksuits, baby-doll tops, and denim miniskirts. Not to mention the plethora of 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… Despite its iconic status, there are still trends we might prefer to forget, such as headbands worn across the forehead.

      From 2010 to 2014, the launch of Instagram, Snapchat, and Vine occurred, while Tumblr was thriving. We often look back and think, What were we thinking? Styles like twee, festival fashion, and normcore emerged, along with trends like peplum tops, statement necklaces, flared skater skirts, platform ankle boots, and high-waisted jeans. And how could we forget the infinity scarves, riding boots, maxi dresses, flannel shirts, crop tops, and Chelsea boots? Then, between 2015 and 2019, model-off-duty style led the scene, showcased by Kendall Jenner, Kim Kardashian, Gigi and Bella Hadid, Hailey Bieber, and Emily Ratajkowski. Fashion enthusiasts were seen sporting Baguette bags, bike shorts, straight-leg jeans, bodysuits, puffer coats, blazers, bucket hats, tiny sunglasses, tailored suits, cutouts, and lug-sole boots. This period also gave rise to the term "millennial pink" and King Kylie.

      Recently, the dissemination of trends began to shift. TikTok introduced micro-trends that altered how style spreads. Phrases like quiet luxury, '90s minimalism, clean girl, balletcore, and the Y2K revival have all had their moments from 2020 to the present. Jelly flats, a childhood favorite, made a comeback, alongside knee-high boots, faux-fur coats, barrel-leg jeans, east-west bags, Mary Janes, and track pants. Skirt lengths transitioned from mini to knee-length. Today, Hailey Bieber and Kendall Jenner continue to be style icons, alongside trendsetters such as Devon Lee Carlson, Zoë Kravitz, Zendaya, Gabbriette, Dua Lipa, and Sofia Richie Grainge.

      While certain styles have changed since 2006—many of us may not be seen in skinny jeans again—some remain consistent: oversized sunglasses are back in fashion. Below are 20 trends that have defined the past two decades.

      1. Kate Moss epitomized low-rise skinny jeans, particularly in her 2008 Glastonbury outfit, paired with classic black Hunter Wellington boots, as Kings of Leon, Amy Winehouse, James Blunt, and more performed at the three-day festival. The polarizing silhouette was the denim trend of the time.

      

      2. When I think of oversized sunglasses, I immediately picture Nicole Richie and Paris Hilton—from Chanel's Shield styles to Tom Ford's Whitney. They have returned as the leading sunglasses trend of 2026, with Khaite x Oliver Peoples's 1967C becoming the most desirable pair.

      3. Velour tracksuits, especially the iconic hot-pink Juicy Couture set, were ubiquitous. Mariah Carey even took it a step further by wearing a capri version.

      4. A double take was in order when I came across a photo of Rihanna in a baby-doll top. It truly was a different era—leading us to our next trend.

      5. Denim miniskirts—particularly those from Hollister and Abercrombie—were all the rage. I recall the outfit formula of pairing a baby-doll top with a denim miniskirt and leggings