I'm Gen Z. My sister is a millennial. Growing up, I had a front-row seat to her fashion evolution. On Monday, it was Kimora Lee Simmons meets Devon Aoki, and by Friday, it resembled Kate Moss on the grounds of Glastonbury—muddy boots and all. When Gossip Girl premiered, she outfitted herself as if she were a Fifth Avenue regular. Then came her twee era, my personal favorite. Zooey Deschanel and Alexa Chung were her icons and mine, too, by default. Nearly 10 years later, I still get phone calls with updates on her latest fashion endeavors.
While working in the industry, I've learned that my sister's inability to hone in on one singular aesthetic isn't unique to her. Vibe shifts are inevitable, and the last 20 years have proved just that. It just so happens to be Who What Wear's 20th anniversary, and after two decades of reporting on trend cycles and celebrity style, we're taking a moment to reflect on how far fashion has come since the aughts.
Ahead, read my retrospective of the 20 iconic fashion aesthetics that defined the past 20 years. Starting with McBling, I've drafted a timeline that spans embroidered Fendi Baguettes, the rebellion of indie sleaze, Peter Pan collars, the flower crowns of Coachella, and Tumblr 2014, making my way to the clean girls, chic Parisians, and vintage archivists who write the aesthetics of today. If you're interested in seeing the progression from "That's hot" to office siren, keep scrolling.
McBling
(Image credit: Getty Images)The early-to-mid aughts were defined by glitz and glamour. Think Paris Hilton celebrating her 21st birthday, Sarah Jessica Parker and her embroidered Fendi Baguette, and Missy Elliott accepting a Grammy in a hot-pink velour tracksuit. Whether people were posing for paparazzi or hanging out at the mall, trucker hats, blinged-out miniskirts, wraparound shades, low-rise jeans, and bejeweled shoulder bags were the norm—just ask SJP.
Von Dutch 99' Rhinestone Tank MANGO Rhinestone Denim Miniskirt fendi Baguette 26424Indie Sleaze
(Image credit: Getty Images)There are only a handful of moments that define a fashion era. Chung and her then-boyfriend Alex Turner at the 2008 Glastonbury Music Festival is one of them. From the mid-aughts to the mid-2010s, there was a spike in hedonism. Music from artists like Arctic Monkeys and LCD Soundsystem and celebrity fashion of the time (e.g., Mary-Kate Olsen in a fur coat, skater skirt, and tights) embraced the maximalism of uncertainty and unregulated authenticity.
Lauren Burnished Leather Moto Jacket J.Crew Boyfriend Jersey T-Shirt frame The Darling ShortUES Prep
(Image credit: Getty Images; Alamy; @emmaleger)This aesthetic undoubtedly correlated with the premiere of Gossip Girl in 2007, and Serena van der Woodsen's and Blair Waldorf's wardrobes were largely responsible for the sudden interest in the East Coast elite. The quiet charm of the Upper East Side and the old money background likely contributed too. Rooted in academia and collegiate styling, pleated skirts, plaid suiting, and pussy-bow blouses became mainstream trends.
Veronica Beard Miller Houndstooth Dickey Jacket Sandro Pleated Skort Reformation Ani Ruched LoaferTwee
(Image credit: Getty Images; Shutterstock)This was an era of peak millennial optimism. Streaming Camera Obscura, debating who's really at fault in 500 Days of Summer, watching Portlandia, wearing Peter Pan collars, saving Alexa Chung outfits on Pinterest, buying vinyls, and cutting bangs after seeing Marlo Thomas in That Girl—that was the twee experience. Falling under the indie umbrella, twee looked to the '60s for A-line and shift dress silhouettes, mingled with hipster-associated media, and flirted with the peril of indie sleaze.
Reformation Silver Bell Bag Miu Miu Poplin Dress Schutz Dafne Leather FlatBusiness Casual
(Image credit: Getty Images)Let's talk about it. By it, I mean statement necklaces. This chunky accessory was a staple among business-casual dressers. Body-con skirts, colorful blazers, peplum blouses, and contrasting prints were equally as popular. While this trend largely lived in real life and on Pinterest boards (guilty as charged), celebrities like Kim Kardashian and Rihanna embraced the corporate-adjacent aesthetic.
BaubleBar Jane Beaded Necklace ZARA Poplin Peplum Top Posse Alice Striped MiniskirtModel Off Duty
(Image credit: Getty Images; Shutterstock)To achieve the unbothered allure of an off-duty 2010s supermodel, you must appreciate skinny jeans. Gisele Bündchen, Rosie Huntington-Whiteley, and Winnie Harlow certainly do. The skintight denim paired with an equally fitted tank, attitude-fueled boots, and an unbothered air became the unspoken outfit formula for go-sees and casting callbacks, and as expected with the skinny-jeans resurgence (I have my reservations), It girls have once again returned to this trusted combo.
Almina Concept U Neck Tank AG Farrah Skinny Jean simkhai Kayla Chelsea BootFestival
(Image credit: Getty Images; Alamy; )It was Coachella 2012. Vanessa Hudgens wore a flower crown, stacked bangles, and a boho duster. Today, we recognize her as a founding figure of music-festival fashion, influencing each Coachella of the mid-2010s thereafter. The vibe was gladiator sandals, cutoff denim, crochet tops, pull-on boots, fringe belts, and teashades. It spread from the muddy ground to downtown L.A., where it died down… until a few years ago. Coachella outfit guides returned to this boho-chic styling, and images of Jasmine Tookes's and Alessandra Ambrosio's festival 'fits resurfaced.
Massimo Dutti Floral Print Flowing Shirt Anna Kosturova Marianne Crochet Midi Skirt Frye Harness 12RTumblr Grunge
(Image credit: Getty Images; Alamy)In the mid-2010s, Tumblr hit its zenith—2014 to be exact. It was a time when long-sleeve tops were flannel, jeans were ripped, and graphic tees revealed your favorite artist. Ultraviolence hit streaming platforms. Divergent was released in theaters. And new additions were made to the lexicon: Gwyneth Paltrow and Chris Martin's "conscious uncoupling" and John Travolta's unfortunate "Adele Dazeem." It was here that everyone found their niche, and esotericism reigned supreme.
MATTEAU Checked Cotton-Flannel Shirt Urban Outfitters Vintage Metallica Graphic Tee frame The Grunge Hang ShortNormcore
(Image credit: Getty Images;)There's no shame in being basic. That was my takeaway from a 2013 report by trend-forecasting company K-Hole, which coined the term "normcore." In direct contrast to the childhood mantra of "Just be yourself," normcore celebrates sameness. When the pressure to differentiate from your peers becomes too much, normcore is a breath of fresh air wrapped in a plain white T-shirt, a pair of modest blue jeans, and maybe an oversize blazer if you're feeling frisky.
ANINE BING Quinn Blazer COS Slim Cotton Raglan T-Shirt CITIZENS OF HUMANITY Blaine JeansGorpcore
(Image credit: Getty Images; @shhtephs; @rebeccaferrazwyatt; @by.regiina; @_imanirandolph)When hiking attire leaves the trail, you get gorpcore. If you're unfamiliar, GORP stands for "good ol' raisins and peanuts," which confirms the granola rumors. It's utilitarian, performance-driven layering that blurs the lines between outdoor gear and streetwear. It's not designer labels that move the needle here. Rather, it's top-notch performance brands like Arc'teryx, The North Face, and Salomon. All the technical information can be daunting to a beginner, so start small. A pair of cargo pants, a windbreaker, and hiking shoes will do the trick.
The North Face Antora Rain Hoodie Uniqlo Utility Volume Trousers salomon XT-6 SneakersClean Girl
(Image credit: Getty Images; @aymiecahill; @monikh; @mobinapeiman; @amaka.hamelijnck)Prioritizing self-care, the end of 2021 marked the beginning of the clean girl era. You can recognize this aesthetic by its no-makeup makeup, matching workout sets, six-step skincare routines, prioritized cuticle health, and absence of split ends. Laura Harrier's and Hailey Bieber's street style are the paradigm—simple silhouettes and minimal makeup that let one's natural beauty shine.
Aritzia The Davis Short Trench Coat Leset Rio Capri Pants New Balance 530 SneakerCoastal Grandma
(Image credit: Getty Images; Shutterstock; @abimarvel; @cassdimicco; @_marisamartins_)Diane Keaton in Nancy Meyers's Something's Gotta Give—or, truthfully, any leading lady in the Meyers universe—and Martha Stewart are the epitome of this windswept, linen-wearing lifestyle. With roots along the East Coast, it predates its 2022 discovery coined by TikToker Lex Nicoleta. In contrast to its laid-back appearance, the coastal grandmother aesthetic takes a lot of effort to look effortless. Everything is hand-selected, from her woven tote to her Bermuda shorts.
Aritzia Airplush Cotton Sail Shirt Boden Kensington Linen Shorts Vince Barcelona Crochet Tot