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On October 3, Sarah Patrick went apple-picking. The weather, she said, was just starting to feel like fall in her quaint Rhode Island town, all crispy foliage and cable-knit wool. Joined by her husband Kiel and their toddler Harry, Patrick plucked baskets of Honeycrisps wearing a uniform entirely New England in measure: Barbour jacket, starched button-up, jeans. 

I know all this, of course, because Patrick's October 3rd is documented in perpetuity on her Instagram, where more than 600,000 followers tune in to observe a life much unlike their own.

Patrick first garnered internet acclaim with "Classy Girls Wear Pearls," an early-generation lifestyle blog documenting, as she writes, "a New England girl's pursuit of quality fashion, friendship and coastal living." In 2008, Patrick and her husband launched their own clothing and accessory line, Kiel James Patrick, with just one product: a fabric bracelet cut from the end of old ties. Their retail empire has only grown since, now a multi-category operation stuffed with Preppy Handbook staples and complete with their very own flagship store atop the yacht-filled wharfs of Newport.

Patrick is a master of escapism. Her J.Crew catalog of a digital footprint sells a certain lifestyle: It's prep personified, from the Madras in her closet to the retrievers at her feet. In this, Patrick isn't alone. 

In recent years, visual platforms like Instagram and even TikTok have fostered this preppier aesthetic, often ironically. The rise of "Christian Girl Autumn" and Caitlin Covington, the influencer behind it, aren't explicitly preppy, per se, but they do exemplify the type of simple, low-stakes wardrobe philosophy into which prep falls. 

For some, the influencer sphere is dominated by avant-basic 20-somethings on TikTok or The Row-wearing photography buffs with bubble couches. Preppy influencers — the vast majority of them white, young and thin — are enjoying their own kind of rampant success. Today, there's an influencer market for everyone, some more aspirational than others.

"Everyone has their own idea of who the most successful fashion influencers are," says Rebecca Jennings, a senior correspondent at Vox who covers internet culture. "There isn't just one style people are gravitating toward. Everything is happening at once, and you have to find someone who's doing something you're interested in or providing something that's tactically useful for you, rather than someone wearing expensive clothes that look like everybody else's."

Of course, prep culture in and of itself isn't inherently accessible. It's still associated with the kind of Hyannis Port leisure activities that are typically seen across the Northeast and New England, often amongst an exclusive set of individuals as privileged in their race as in their class. Stylistically, prep has its roots in 1920s-era Princeton University, where, according to historian and curator Deirdre Clemente, personal style thrived — within certain parameters.

A century later, today's prep has evolved into something much wider. People of color have worked to diversify the imagery associated with a style that remains inextricably linked to race and class. Brands like Recreational Habits, a just-launched luxury label, is conscious to celebrate "the preppy American spirit through an inclusive lens." 

"The 'new prep' is really more about growing up and understanding that you can keep culture and sophistication all together," says co-founder Marlon Muller, who created the brand with his wife, Barneys New York and Kith alumna Jackie Skye Muller.

On the pages of its iconic catalogs of the 1990s, meanwhile, J.Crew helped to introduce unfussy basics that could be worn from a stately luncheon to an impromptu bonfire. It's still how preppy clothing is constructed: convenient to embrace, yet still evocative of the type of lifestyle where the cashmere is always freshly dry-cleaned. That's certainly how Patrick and other preppy creators dress, with splashy prints drizzled onto easy, well-tailored silhouettes.

Carly Riordan launched her lifestyle blog, "The College Prepster," while a freshman at Georgetown University in 2008. She's since abandoned The College Prepster moniker, now updating her 230,000-odd Instagram followers under a more self-explanatory handle, @carly, and a website with an eponymous domain. She's also authored a book, "Business Minded: A Guide to Setting Up Your Mind, Body and Business for Success," due out this December. 

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As Riordan's grown up, so has her platform which now encompasses topics ranging from anxiety and fitness to travel and motherhood. Still, her wardrobe is as preppy as ever. Find her posing in a ribbed mock-neck sweater on the beach in Nantucket or a striped tee to match her infant son — time-honored pieces, worn simply. As San Francisco-based creator Kimara Mitchell explains, such is the prep mystique.

"Prep is about timeless pieces and how you mix them and make them feel more modern," says Mitchell, who serves as the creative director for Quay Australia and previously worked as an art director at Banana Republic. "Prep can be a piece here and a piece there, and you could potentially mix it with something more avant-garde and fashion-forward."

Mitchell herself has been blogging since 2004, introducing personal style into her digital presence in 2010. While she wouldn't describe herself as a "preppy blogger," per se, she implicitly understands the nature of prep influence, still incorporating certain prim-and-proper tenets into a sophisticated sartorial palette.

"I grew up on the East Coast," she says. "I went to a private school. I remember going thrifting before I went to college and finding a vintage Ralph Lauren blazer that had an embroidered crest on it. I just wore it to death, and did the whole thing with the button-down and the popped collar and the pegged jeans and the loafers."

For Mitchell, much of the preppy influencer's allure lies in their accessibility, which, for the Instagram generation, entails how easy it is to recreate. Even fast-fashion mega-retailers like Shein have taken note, where shoppers can head to their e-commerce site to peruse $11 tartan skirts and $21 tie-neck peplum blouses. And in the last year and a half, the style has broken new ground across creator and retail landscapes alike.

"During the various lockdowns since the start of the pandemic, many people turned to social media to escape what was happening in the world and often became invested in trends that showed a certain lifestyle, style or way of living that was either inspirational or comforting," says Aimee Howell, managing partner at London-based influencer-marketing agency TAKUMI.

In the case of mega-influencers like Patrick or Riordan, neither of whom responded to Fashionista's request for comment, they may be going one step further, inspiring followers to spend their Saturday night at a candlelit dinner party, cracking into Maine lobsters, toasting flutes of champagne. It's what Howell likens to a rebuttal of the "'new money' rich" aesthetic — she offers Louis Vuitton tracksuits as an example — that's dominated the last decade.

"The fashion conscious now wants something new and classic, a throwback to the times when living a life of luxury — drinking fine wine, lounging around your country estate with not a care in the world — was something to aspire to," she says. "It's a direct response to the 'always-on' work culture millennials have been brought up in, with preppy influencers selling elegance and an escape from the norm."

Even still, they're marketing more than permanent residencies on Martha's Vineyard. With such evergreen closets, creators are tapping into the millennial- and Gen Z-centric priorities of sustainability. In a true preppy wardrobe, no staple goes to waste.

"My sophomore year of college, I distinctly remember going to the J.Crew store at South Street Seaport," Mitchell says. "I had saved my money and was so excited to buy this rollneck sweater." She still has it, and busts it out on those chillier Bay Area mornings. "They're pieces you could theoretically have in your wardrobe for years versus something that's so specific in its print or its color that you might not see a year from now."

There may always be an appeal to minimalist, Ivy League-inspired clothing because, as Jennings explains, this lifestyle of wraparound porches and canvas-wrapped Adirondack chairs remains truly inaccessible for so many — despite its uniform saying otherwise.

"Prep always comes back around once it's been long enough that we've been without it," she says. "But now there's a new way of discovering it, and it feels novel."

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