Ten years ago, while working as a trend forecaster for two prominent teen retailers who capitalized on the all-American preppy lifestyle, I witnessed a shift in the millennial mindset. Photographs at Coachella, Roskilde, and Glastonbury revealed festival street-style gaining momentum each year, and the iconic, casual, preppy look gradually disappearing as festivals grew in size and popularity. Preppy was classic. The styles had a long shelf life on the retail floor. Fast fashion—based on recent runway trends—needs to be updated weekly.

How did the preppy lose the popularity contest, and what factors caused its disappearance?

Fast. Festival. Fashion.

Put simply, festivals celebrate individuality, inclusiveness, and diversity, which run counter to preppy’s conformist and exclusive lifestyle. Music is an expression of self, associated with authenticity. This anti-establishment environment naturally brews a backlash against the clean-cut preppy look.

Fast fashion resonates with the young demographic. Shorter attention spans and increasing amounts of visual information mix with slim budgets and creates a yearning for the newest and coolest at disposable prices.

The retail landscape changed drastically in the wake of the 2008 recession. Brands such as Sweden’s H&M, UK’s Topshop, and Japan’s Uniqlo expanded stateside, increasing competition. This retail globalization along with rising costs of production and raw materials saw US brands struggling amid declining comp sales and store closures. Many brands, such as Abercrombie & Fitch, are now restructuring their business models and shortening their production cycles to compete against fast retail giants like H&M and Forever 21. Teens are still grappling with 19.1% unemployment. With less disposable income to spend, they are more price-conscious than ever before. And given the choice, they choose to spend on technology over clothing, which has compromised fashion retail across the board.

Instead of designing four to six collections a year, fast fashion delivers new assortments to stores every week. The design, manufacturing, and distribution of clothing used to be a stable three-month production cycle spanning the globe. The quarterly cycle has collapsed across much of the industry, to just two weeks. This fast-fashion movement is led by Korean-American manufacturing families in LA, most prominently the Chang family, which owns the Forever 21 chain. Their LA-based design offices allow them to leverage celebrity culture and react to trends quicker.

Meanwhile, Classic heritage looks are cast to the wayside. Even J.Crew ditched its traditional conservative look in favor of a quirky preppy twist to make itself more relevant. Are there preppies still around? Yes, there will always be Brooks Brothers and Ralph Lauren customers in New England, the Hamptons, and the local country club. These brands cater to clientele living or aspiring to the American Dream, pursuing an affluent and traditional lifestyle. Classic styles have clearly taken a back burner in the fashion market.

Music and Celebrities Go Hand in Hand

Coachella is LA’s fashion week. There is no other festival like Coachella where mere mortals have the chance to rub elbows and share the air with the famous and almost famous. Celebrities are now paid lucratively to attend Coachella promoting and wearing a particular brand. Lacoste paid Glee star Lea Michele $20,000 to wear and Instagram “#Lacoste #OOTD (outfit of the day) before Outkast takes the stage.” The culture of festivals and fashion has been affected by Corporate-chella. Are the days of a Woodstock-like festival sans brand and celebrity endorsement over?

Amy Winehouse was one of the first influential celebrities to skew the preppy look. After coming onto the scene around 2005, her grungy, retro-rock look ushered in the first hipster wave. Simultaneously, actress Sienna Miller honed her boho lux style, mixing high-end with high-street, wearing Topshop dresses accessorized with a Balenciaga bag. The new hippie was a far cry from the Woodstock hippie.

Welcome to 2014, with artists such as Rihanna, hailed as a fashion icon, traipsing the festival grounds. The masses notice. Her coveted edgy look is anything but preppy. She’s bold and takes chances with everything she wears. It’s a field day for the paparazzi when the reigning queen of cool is photographed partying at Coachella. What she is wearing will most likely be sold out in stores or knocked-off within weeks. Whether her style is authentic or a strategic business move, this savvy brand building is corporatizing the business of cool.

Similarly, telephoto lenses are trained on Kate Moss at Glastonbury each year, whether she is accessorized with Hunter wellies or Pete Doherty on her arm. Kate Moss is the antithesis of preppy. Kate Moss epitomizes the rock ‘n’ roll lifestyle that millions of girls want to emulate. Kate Moss gets them to spend billions.

Remember Britney Spears’ sexy yet canned, wholesome schoolgirl persona back in 2000? That was an era of popped collar polos and brand logos, all the rage with teen consumers. That look doesn’t resonate anymore and it’s taken retailers an unfortunate amount of time to figure out how to evolve.

Street-Style Photography Made the Festival Famous

Street-style photography inspires designers and consumers, and over the past decade has made full-time careers of documenting stylish looks. Once fashion bloggers such as The Sartorialist burst onto the scene curating street style in 2005, the importance of quick documentation was cemented in the fashion industry. In 2010, Instagram brought an obsessive wave of millennials snapping daily outfit selfies striving for uniqueness, yet ironically having a certain quality of sameness to them.

“Cool Hunters” flock to festivals to confirm and gauge new trends in the marketplace. Along with Coachella, the fashion industry keeps its finger on the pulse at Glastonbury in England and Roskilde in Denmark, two of Europe’s largest music festivals, where brands set up festival pop-up shops.

Photo by the Confluence

Brands actively pursue the festival-fashion market niche. There are over 7.5 million results for Coachella on Google. In 1999, 25,000 fans attended the festival during its inaugural weekend. Attendance has now surpassed 200,000 people. In the early naughts, fashion brands didn’t align themselves with festivals. They weren’t viewed as obvious aspirational fashion destinations. Concertgoers were music-minded, wore literal hippie and utilitarian looks, and didn’t peacock for photographers. The fashions now have a draw of their own. The stage no longer applies only to the music but, rather, the desire to see and be seen.

Festivals directly influence magazine editorials and brands. Even after the lights go down on the final act, attendees preserve those “festival high” memories by incorporating festival dressing to their daily lives. Whether it be fashion sites like Refinery29 highlighting the new Normcore trends to watch for or Urban Outfitters festival references in its lookbook assortment, festival fashion equates to billions of dollars in sales for the fashion industry during the spring and summer seasons.

Social Media's Role

New technology and e-commerce paved the way to meet insatiable consumer demand as well as made demand insatiable. Facebook, Instagram, and Twitter have enabled a generation of fashion pundits to instantly comment, give feedback, and promote brands. It’s also generated a much broader conversation about fashion. Broadbrand technology has opened up dialogue between brands, celebrities, and consumers, which foster faster fashion. Photos of runway looks are now delivered in real-time and available to everyone with a phone and Internet connection. Suddenly, a six-month wait for the latest and greatest seems absurd. Technology has changed the fashion industry and brands that don’t adopt will be left behind. As Diane Von Furstenberg said, “Ignoring the Internet is total madness, being active is indispensable to growth and being relevant. It helps your business to be truly global and multi-generational.”

Festivals Have Changed the Fashion Industry, and Fashion Is Changing Festival Dynamics

Festivals are powerful platforms for brands to reach audiences and glean info from them. They have the ability to steer styles and to experiment with innovative marketing strategies.

According to Ryan Newey, Creative Director of Glastonbury, “Brands have become as much part of the entertainment as the performers themselves. They need to earn their admission to music festivals by increasing the fun rather than pursuing their own narrow agendas. Music fans are quick to decry brands’ festival activity as ‘too corporate,’ which implies insincerity and involvement only for selfish gain.”

Photo by Jaswooduk via Flickr Creative Commons

Has Coachella succumbed to over-the-top marketing and commercialization? Yes, some might say. Brands clamor to sponsor events tied to Coachella to gain visibility and credibility within this demographic. H&M, Guess, Lacoste, Marc by Marc Jacobs, Adidas, Opening Ceremony, Old Navy, aerie, A/X, Nylon, and Harper’s Bazaar have tied their events and marketing to Coachella, creating cool experiences.

Festival fashion is currently at its height. However, fashion is constantly changing. The market has become increasingly oversaturated with festival fashion. The backlash has already begun against Coachella clichés such as the misappropriation of cultural adornment like Native American headdresses and bindis. What’s next?

Festival fashion is no longer the look of the counterculture; it’s the mainstream now, a symbiotic cycle of brands and consumers looking to inspire and be inspired, potentially self-cannibalizing. How will festival fashion evolve? How can it evolve? Festivals, celebrities, technology, and the economic downturn have fundamentally changed the speed of fashion trends and production. Will more socially conscious brands and authentic artisan accessories and apparel move and shift this market in the future, or will preppy have an encore?

Chrissie Lam is a modern day gypsy, turning “Cool-Hunting” into a lifestyle and a means of discovering unique & creative talent in a variety of forms. She has curated for multi-billion dollar fashion brands and traveled to over 70+ countries. As the founder of The Supply Change, she connects artisan groups in developing countries with fashion brands in an effort to redefine the supply chain. Follow her on Twitter, Facebook  and Instagram.