20 Fashion Aesthetics Over 20 Years: All the Vibe Shifts That Mattered

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

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.

Indie Sleaze

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.

UES Prep

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.

Twee

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.

Business Casual

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.

Model Off Duty

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.

Festival

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.

Tumblr Grunge

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.

Normcore

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.

Gorpcore

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.

Clean Girl

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.

Coastal Grandma

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.

Coquette

This aesthetic is also described as balletcore, depending on where you fall on the "lover girl" spectrum. There's a good chance Black Swan is in your Letterboxd top four, Lana Del Rey is your most-listened-to artist, and you have a soft spot for the lace-trim trend currently sweeping FYPs everywhere. While coquette precedes balletcore, the two often go hand in hand. Ballet flats, leg warmers, ribbons, bows, pastel colors, and ruffles unify the two.

Scandi Street Style

Likely linked to the rising popularity of Copenhagen Fashion Week, Scandinavian street style is characterized by its boxy, oversize silhouettes; unexpected color combinations; contrasting textures; and eye-catching footwear. They're the first to style the more controversial trends—ahem, balloon trousers, scarf belts, and capris—and you can always count on the Scandi style set for unpredictable pairings, like polka dot on polka dot.

Quiet Luxury

Quiet luxury is the ultimate lesson in "less is more." It's quality over quantity. It's logoless brands. It's subtle signaling. Consider the correct buy-in (a The Row trench coat or Khaite trousers) a homing device for fashion insiders. Invest in basics, build a capsule wardrobe, and rely on the classics. Don't mistake this for uniformity; personal style is still appreciated.

Sportif

You know the sportif aesthetic is done well when you're presented with two pieces that, on paper, should never go together, like running shorts and dainty kitten heels, but surprisingly complement each other. It's the juxtaposition that makes this casual athleticwear so enticing, and Bella Hadid knows it all too well. She was previously spotted in a rugby polo, a plaid midi skirt, and Adidas Sambas.

Parisian Chic

Despite the London address on her birth certificate, Jane Birkin set the standard for the Parisian aesthetic. Her lessons in laissez-faire dressing continue to dictate the wardrobes of modern French women—basket bags, lived-in denim, tailored blazers, and crisp button-downs. Of course, the grip that the color red has on Francophiles should also be mentioned. There's the red lip, Jeanne Damas's ruby pumps, and Audrey Hepburn wearing a scarlet gown on the steps of the Louvre in Funny Face.

Office Siren

Calling on the corporate attire of the '90s and early aughts, the office siren archetype is Gen Z's way of romanticizing the inevitable 9-to-5. Instead of rose-colored lenses, it's a pair of Bayonetta glasses. Despite their corporate origins, the trends that define this aesthetic are oddly not office-appropriate. Low-V-neck tops, cinched button-downs, ultra-miniskirts, low-rise trousers… The list goes on. Icons like Gabbriette Bechtel, Gisele Bündchen in The Devil Wears Prada, and Hadid stick to a muted grayscale color palette that evokes the mundanity of the corporate life cycle.

Minimalism

From Carolyn Bessette Kennedy to Sade, the '90s influence on contemporary dressing is undeniable. You can chalk it up to the streaming platforms and their role in this revival (looking at you, FX's Love Story), but Gen Z's nostalgia-driven anemoia is partly to blame as well. What makes this aesthetic so pleasing to the eye isn't just the limited color palette. It's also its unclutteredness. Jewelry is few and far between, logos are hidden, and silhouettes are uncomplicated.

Fashion Archivists

This one's for all my vintage lovers out there. Your closet resembles a cabinet of curiosities: fringed shawls, artisan pillbox hats, Bianca Jagger–inspired slips, storied leather goods. Your affection for secondhand shopping doesn't limit you from buying new, but these new pieces must be worth conserving for future fashion historians like you. A look that lives rent-free in my mind? Paloma Elsesser in a Margiela F/W 97 dress-form tunic. On the new-in side, a Fendi Re Edition Baguette is a valuable addition.