By Selling a Feel-Good Lifestyle, Preppy Brands See Consistent Success in a Trend-Driven Market

This could explain why that little pink whale always looks so happy.
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Looks from the Vineyard Vines for Target collection. Photo: Courtesy of Target

Looks from the Vineyard Vines for Target collection. Photo: Courtesy of Target

Close your eyes and think about what "the good life" means to you. From living out your days in a tropical paradise to becoming the next Chiara Ferragni, the possibilities are endless. Selling a carefree lifestyle is a compelling marketing tool, and no one knows that better than Shep and Ian Murray, co-founders and CEOs of Vineyard Vines, the colorful brand known for eye-catching ties and an iconic pink whale logo. After all, that dream is what got the brothers into the retail industry in the first place.

"Growing up, we'd joke that we'd wait nine months to spend three months of summer living the good life — time we'd spend boating, sailing and fishing — on Martha's Vineyard with our family and friends," says Shep of the Vineyard Vines ideology origins. This pursuit of happiness eventually led the brothers to quit their banking jobs in 1998 to sell neckties out of their Jeep instead. Before long, this summertime mentality became their full-time one, and they've never looked back. 

"That ethos stuck with Vineyard Vines throughout the years and 'every day should feel this good' became our brand motto, our mantra, our way of life," explains Ian. "That's how we live our lives and that's how we've built Vineyard Vines." 

When the brand's Target collection rolled out nationwide on May 18, the Murrays hoped to bring their version of the good life to the masses. While this collaboration sent loyal Vineyard Vines fans into a tizzy, it likely received some eye rolls from people who don't get the appeal of the prep aesthetic, or understand why you'd ever want a whale (not to mention dozens of them) printed on anything, ever.

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Why do some people have such a knee jerk reaction to preppy styles? There are a few reasons that go beyond personal preference. The first is the notion that "preppy" brands, ones that typically rely on bold colors and whimsical patterns, are neither chic nor sophisticated, and therefore should not be associated with the fashion world. This has been an ongoing debate for years (just look at this heated take and rebuttal). Beyond its affiliation with the one percent, the oversaturation of preppy style in the early- to mid- 2000s also lingers as a not-so-distant memory. This period of time still triggers unsettling, Tommy Girl-scented visions of ribbon belts, clashing patterns and layered Polo shirts (all with the collars popped, of course). The assumption that prep directly correlates to a garish way of dress — one that pairs loud bow-ties with a seersucker suit, a madras shirt and an equally obnoxious bro — remains a very real, frat-tastic stereotype today.

In reality, however, this is the most intense iteration of the aesthetic that's seldom worn day-to-day. "That might be something you can get away with wearing at the Kentucky Derby, but for everyday wear, I think that's a little extreme," says prep influencer and designer of an eponymous label Kiel James Patrick. Patrick's wife, fellow influencer and business partner, Sarah Vickers agrees: "For a few years, [prep] was starting look like a costume again for a lot of people, but now it's gone back to a more organic place," she says. According to Patrick and Vickers, there's such a wide range of what's considered "preppy" today that the term is used loosely and has gotten watered down. 

"For us, we like New England style, so we prefer those classics that are functional for going from to work to sailing to a family cookout," adds Patrick. His and Vickers's practical, yet photogenic eye for style is exactly why they've amassed over a million followers and launched a booming business selling these traditional wardrobe staples.

Patrick's version of prep is close to the definition as a style that goes back to upper-class leisure activities (like tennis, sailing and squash) and private university-preparatory boarding schools across the Northeast and New England. And in case you missed Fashionista's trend report, the prepster look is making a comeback this year. "Preppy today doesn't necessarily have to be Brooks Brothers," says MaryKate Boylan, fashion market editor at Town & Country. "The Celine Fall 2019 woman is the ultimate Upper East Side lady, but it's cool because it's Hedi Slimane." But it doesn't stop there, and goes beyond Ralph Lauren: "Thom Browne has made classic, preppy dressing cool by giving it a twist of shrunken fits and plays on proportion or unexpected prints and patterns," adds Boylan, and "Loewe has its own version of the Patagonia fleece."

Accessories from the Vineyard Vines for Target collection. Photo: Courtesy of Target 

Accessories from the Vineyard Vines for Target collection. Photo: Courtesy of Target 

Even when it isn't splashed across the runways, preppy dress doesn't disappear like a passing fad. That's because its heart and soul is rooted in classic, iconic styles. Items like double-breasted blazers, chinos, tweed, loafers, polo shirts and trench coats will always be around, and "most people have some of these elements in their closet whether they consider their style preppy or not," says Boylan. "Just look at the way John and Jackie Kennedy dressed, or many royals from the last eighty years. You could wear many of those outfits today." 

Carly Heitlinger, the popular blogger more commonly known as Carly The Prepster, echoes Boylan's sentiments. "Almost everything I used to post about is still in style because it is a timeless look," she says. "I love that sweaters I got in college are still [ones] I reach for today."

Despite its timeless nature, being a "prep" still isn't the coolest thing to be defined as, even after stripping away the stigma surrounding it. "You don't see Bella, Gigi and Kylie wearing shift dresses with Jack Rogers [sandals] and a sweater around their neck," Boylan explains. "You see them wearing these hip, young Instagram brands you haven't heard of before and major fashion designers. They're showing skin, wearing athleisure and never repeating an outfit." 

Preppy may not be "cool," but that's the thing some people don't get about lifestyle-centric brands: it doesn't matter to them. According to Shep and Ian, Vineyard Vines avoids chasing trends altogether and instead focuses on creating great products. "We've never considered ourselves a fashion brand," they say. "What we've been doing is contemporizing preppy with not only fit, but also by fabrication. We take performance fabrics — stretch, polyester, wicking — and put them into classic styles, so you're able to look preppy, but also relevant in today's world."

Delivering well-made styles that cater to a specific way of living has proven to be a cornerstone of other companies' success as well. Take Lilly Pulitzer, the Palm Beach designer known for her playful prints, affinity for the color pink and love of pineapples. "A big part of our brand and company strategy is to really focus on the authentic needs of someone who is living a resort lifestyle," explains Michelle Kelly, Lilly Pulitzer's CEO. "We are very much thinking about a customer today, who is either going on vacation or living a life under sunny skies, and what clothing would serve her needs." Their happy-go-lucky approach to fashion has amassed a loyal following of women who wear Lilly simply because it makes them feel good. The brand celebrated its 60th anniversary this year, proving that its Florida-inspired heritage is just as relevant to its customer base today as it ever was.

Southern Tide, on the other hand, has placed emphasis on its Southern roots. "When we started out ten years ago, our founders didn't think about preppy, they just thought about bright colors and a lifestyle that was fun," says CEO Christopher Heyn. "The most important thing for us, outside of making great product, is we want the person to say, 'hey, I want to be there, I want to be with them.'" This feeling of being part of something bigger gives consumers an incentive to buy these more traditional types of clothes, because truly, how many polos or pairs of khakis do you really need? "You have to have a reason to buy this," Heyn continues. "You need to sell a collection of merchandise in an environment that does more than just fill in basics and inspires people to come back."

One lucrative way to do this is through partnerships that drum up hype and offer customers new ways to engage. "Fans of most brands go crazy when there are capsules at places like Target or H&M and they can get coveted pieces for a fraction of the cost," explains Boylan of the fanfare surrounding these launches. "It just goes to show that these brands have an extremely loyal fan base as well as an admiring customer who maybe can't afford the real thing, but can shell out $20 to $50 for something."

Shoppers at the Lilly Pulitzer for Target pop-up shop at Bryant Park Grill in New York City. Photo: Cindy Ord/Getty Images for Target

Shoppers at the Lilly Pulitzer for Target pop-up shop at Bryant Park Grill in New York City. Photo: Cindy Ord/Getty Images for Target

Lilly Pulitzer has seen firsthand the power of limited-edition designs and has teamed up with everyone from Goop to Pottery Barn. (Who can forget the success of their sold-out-in-minutes Target collection in April 2015? It turned into a full-fledged shopping frenzy with some items getting resold online for more than double its original price.) Lilly Pulitzer's Kelly adds that, above anything, these collaborations are about strengthening the brand's community: "It was a pretty special moment and it was more than just the value that was offered. It had to do with friendship: People meeting each other, standing in line that morning. Everyone had something in common. They were all there for the same purpose."

Capsule collections are also designed with the hope to get products in front of the eyes — and hopefully into the hands — of new clientele. "Our partnership with Target provides a powerful opportunity to expand our reach and spread our message of 'every day should feel this good' far and wide," explains Shep and Ian. With over 300 items, most of which are priced under $35, everything was designed "for creating the ultimate summer gathering with friends and family." Vineyard Vines's goal is to show people that they can make something as simple as a weeknight dinner feel like the good life, whether that's through decorating with an island-inspired table runner, wearing a red, white and blue romper, or using a nautical serving tray.

Of course, it's okay if not everyone shopping at Target wants to bring the happy pink whale logo home with them. But even if you're in the anti-whale contingent, you can still recognize that it brings other people happiness. At the end of the day, everyone is looking for something to make them smile — which is exactly why feel-good brands like Vineyard Vines are here to stick around well beyond next summer, and are able to see consistent success in a largely trend-driven market.

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