Mark Kennedy, a 56-year-old newspaper columnist from Chattanooga, Tennessee, first noticed the pervasiveness of preppy clothing brand Vineyard Vines last fall while vacationing on a Disney cruise. He spotted a family of four wearing matching blue polo shirts emblazoned with a little pink whale on the chest.

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The brand seemed to follow Kennedy for months—first at a Christmas party, where friends told him Vineyard Vines was the most desirable label at their kids’ prep school, and then again, weeks later, when Vineyard Vines opened a pop-up shop in town and his sons, ages 8 and 13, eagerly purchased several pairs of colorful pants.

"It’s the kind of clothing you can expect to see at a golf course," Kennedy says. "The pastel pants are very big, and the kids love the pullovers."

Since Vineyard Vines launched in 1998, it’s spent time building a wildly dedicated fan base, and despite its relative youth, is giving longtime prep stalwarts like Lilly Pulitzer and L.L. Bean a run for their money.

There are currently 55 Vineyard Vines stores nationwide, catering to men, women, and kids alike. The brand brought in $308 million in revenue during the last fiscal year, according to Privco. It has the strongest presence on the East Coast—in the New England area specifically, where its roots were first planted—but has spread across the country over the years, with several stores in California, Texas, and Missouri.

"With no money or experience, we proved that the American Dream is alive and well."

The protagonists in the Vineyard Vines story are brothers Shep and Ian Murray, two self-described "Madison Avenue guys" sick of the daily grind who stepped away from corporate life to sell ties "so we wouldn’t have to wear them anymore," as per the first page of the Vineyard Vines catalog. "With no money or experience, we proved that the American Dream is alive and well."

While the American Dream narrative is perhaps hard to reconcile with the Murrays' background (they grew up in Greenwich, Conn. and summered at Martha’s Vineyard), their definition is less about upward mobility than it is about making money doing something you love. As the brand's motto states, "every day should feel this good."

"We’re a brand with a story. You can still have fun and make a living—you just have to give two weeks' notice, which is exactly what Ian and I did, " Shep says with a grin one evening in December.

We’re standing inside Vineyard Vines’ first New York City store, strategically located on the Upper East Side. The grand opening is hopping, feeling more like a Newport clambake than a freezing winter night in Manhattan. Everyone's dressed in seersucker and plaid while a bow-tied sales associate passes out beer in custom Vineyard Vines koozies. A handsome man has been hired to sing songs from bands like the Eagles over in the corner.

The mannequins in the kids’ section look like mini bankers, and there’s an entire wall of ties.

The interior of the new store, like all Vineyard Vines stores, evokes a shop in a New England beach town. The cash registers sit on the stern of a boat and massive models of game fish hang from the ceiling. There are plenty of flip-flops and baseball caps on the shelves, in addition to blazers, cashmere sweaters, and critter pants. The mannequins in the kids’ section look like mini bankers, and there’s an entire wall of ties with tiny sailboats, fish, palm trees, seashells, and American flags on them.

"We grew up constantly around sailing communities, fishing communities, yacht clubs, country clubs, golf courses," says Shep. "We use icons of what we call the 'good life': boats, Nantucket, golf, tennis. It's very classic American—prep school meets Wall Street. People just want a little bit of fun in their wardrobe. When we started, we said, ‘Why not help people dress for those great life activities?’"

Targeting their customers explicitly is one reason why the brand has taken off so well in the prep market.

"The brand is not ashamed to address their customers head-on," notes Fred Moore, president and CEO of Big River Advertising in Richmond, Va. "If you try to talk to everyone in the market, you’ll connect to no one. Vineyard Vines is very clear about who their customers are. It's created brand zealots who like to be strongly connected to a certain group. They become the sales people."

This has translated to plenty of cash for Vineyard Vines. Last year, the brand enjoyed a 43 percent revenue growth, according to Dev Mukherjee from Privco. In 2010, the brand banked $81 million in revenue. Two years later, it brought in $151 million. By 2013, revenue hit a whopping $215 million before soaring to $308 million last year. Vineyard Vines declined to confirm these numbers to Racked.

By 2013, revenue hit a whopping $215 million before soaring to $308 million last year.

One place in particular Vineyard Vines does remarkably well in is on college campuses, notes Mukherjee. This comes from strategic partnerships the brand inks with schools. It makes exclusive items for colleges like George Washington University, University of Maryland, University of Miami, Virginia Tech, Boston College, and Indiana University, among others. Mukherjee notes that items like bow ties with college logos make the brand a favorite among students and are the reason the company is able to compete with well-established labels like Ralph Lauren.

"They have what would appeal to college kids: they are cool and preppy, but they also have college-specific lines," says Mukherjee. "Their partnerships with colleges and sports brands are the biggest differentiating factor that separates them from older brands."

Adds Kennedy, "It seems like college kids are the trendsetters, because the trend filtered down to high school and then middle school."

Vineyard Vines’ aesthetic isn't all that different from that of other clothing companies, explicitly preppy or otherwise, with its polo shirts (available in every color, of course) and pleated miniskirts. What it provides, however, is a sense of belonging. Customers relish the brand’s ability to make them feel like a part of a group that is well-dressed, well-educated, and well-vacationed.

Customers relish the brand’s ability to make them feel like a part of a group that is well-dressed, well-educated, and well-vacationed.

"Prep is essentially an upper class look. There is a lot of desirability behind it, to dress the part of the higher society that goes yachting and plays polo," says Francesa Munson, head of retail and product analysis at WGSN. "There are wider implications to the healthy, outdoorsy lifestyle. At the end of the day, Vineyard Vines sells the same classic pieces that anyone can buy at the Gap, but it comes down to the branding and the lifestyle they are selling that gets the customers on board."

Carly Heitlinger, a New York City prep blogger and frequent Vineyard Vines shopper, agrees that the appeal of the brand has a lot to do with how the clothes make shoppers feel.

"It’s about what it represents more than anything," she says. "Clothing is a way for people to express themselves, to show what they want or hope to be like. People who wear Vineyard Vines might not be at the beach, and might not have ever even sailed, but it’s just another way they can identify themselves. It’s a fun lifestyle to be associated with."

Another selling point is the brand's surprisingly reasonable prices, which are comparable to those of competitor J.Crew.

"It’s like a grownup Abercrombie and Fitch," Jill Vanderlinden-Starace, an avid Vineyard Vines fan, posits at the store opening. "The clothing is good quality and it attracts customers because of the price."

"Where Brooks Brothers has lost their soul, Vineyard Vines has stayed true to their story."

Part of the Murray brothers' strategy is making sure not to grow too quickly in an effort to make their massively successful company seem small, desirable, and elite to shoppers. While Ian says that the brand has plans to open a dozen stores in 2015, he contends that the expansion is carefully considered.

"We want to be better, not necessarily bigger," he explains. "We’re only going to grow if we feel like we can deliver the experience that we’re giving now or better. It takes a long time to get a product right. I think it took us ten years to get our women’s business right. We continually didn’t do as good a job, and now, for the first time in a couple years, our women’s business is doing really well."

This slow and conscientious growth is another reason why prep enthusiasts are flocking to Vineyard Vines instead of heritage brands like, say, Brooks Brothers.

"Shopping at Brooks Brothers used to feel like you belonged to a club. Now it feels like it got sold to a corporation," muses Moore. "It used to be a special event when there were Brooks Brothers sales—now there are sales all the time and they just keep opening up more outlet stores. All great new brands come around to fill a void that’s been left by a former player, and where Brooks Brothers has lost their soul, Vineyard Vines has stayed true to their story. You can feel their character and authenticity in everything they do."