Spoof Black Dog t-shirts being sold in Martha’s Vineyard in August 1997. (Photo: Getty Images)

The Black Dog is small chain of bakeries, along with one restaurant/tavern, on the island of Martha’s Vineyard, an island about an hour and a half by ferry off the coast of Massachusetts’s Cape Cod. The tavern and the bakeries are famous, though not for its dining experience; they do not serve particularly notable food or pastries (the tavern has a mere three and a half stars on Yelp), and while the view from the tavern out to the harbor is lovely, Martha’s Vineyard is chock full of lovely views.

No, the Black Dog is known globally for its merchandise.

The company sells t-shirts, sweatshirts, caps, neckties, spandex bike shirts, stainless steel cocktail shakers, espadrilles, and wrought iron toilet paper holders, among many more, all boasting the silhouette of a black labrador. That image has become an icon, a shorthand for Martha’s Vineyard, and of the island’s changing fortunes. Thousands and thousands of t-shirts have been sold. The president of the United States has testified in front of millions of people that he gave Black Dog merchandise as a gift. It’s an object lesson in the power of branding, and later on, for how it handled being attached to one of the biggest political scandals of the last century.

In most of the Northeast, wearing a Black Dog t-shirt or sipping coffee from a Black Dog mug means one thing: I have been to the Vineyard. And these days, that’s not such a humble thing to brag about.

 At 87 square miles, Martha’s Vineyard is big enough to have several towns and a few working farms. Of the three main towns on the island (Edgartown, Oak Bluffs, and Vineyard Haven), Vineyard Haven is the smallest, but has the most-used harbor to transport visitors to and from mainland Massachusetts.

Up until just a decade or two ago, Martha’s Vineyard was an isolated fishing village, with a small population mostly consisting of people who make their living from the sea.

“In the 1970s, Captain Bob Douglas, who was a sea captain based out of Martha’s Vineyard, opened a place that didn’t really have a name,” says Nancy Gardella, executive director of the Martha’s Vineyard Chamber of Commerce. The place, opened on New Years Day, 1971, was a tavern, though not in the usual sense, as Vineyard Haven was a dry community up until a law allowing alcohol was passed in July 2012.

The interior of The Black Dog store in Mashpee Commons. (Photo: John Phelan/WikiCommons CC BY-SA 3.0)

The tavern got its name simply. “[Douglas] had always had black labs, his whole life, on the boat with him,” says Gardella. “He was kind of known for having black labs.” One particular dog, which boarded Douglas’s ship shortly before he gave up full-time sailing, was named the Black Dog, after a pirate from the book Treasure Island who’s missing two fingers on his left hand. And so the tavern became known as the Black Dog.

“Until just a handful of years ago, there was no other place to eat on the harbor in Vineyard Haven. So it was a great place to grab a bite while either coming from or going to the ferry,” says Gardella. Vacationers leaving the island would stop for a bite at the charming, nautical tavern on the harbor, and when the Black Dog started selling nice, minimalist t-shirts with a picture of a black dog on the front and “Martha’s Vineyard” written on the back, people started buying those shirts, too.

At first, it was only a local mark of pride. ”Wearing one meant you were a groovy wharf kid who hung around with James Taylor and Carly Simon at the No-Nukes concert,” said Paul Schneider, a writer, told the New York Times. ”At one point we were all in agreement that it was the coolest thing on the coolest island.”

But once the merchandising engine got started, the owners of the Black Dog kept it rolling. The Douglas family bought two D-class tall ships, a baroque, pirate-y looking vessel, and hung Black Dog flags from them. The Black Dog almost seemed to welcome visitors and wave them goodbye. And those visitors could buy t-shirts and other gear, but it wasn’t easy. “The brilliant marketing story goes on that in the early 1990’s merchandise was only sold at one store and a limited number of people were allowed in at one time which created extensive demand and lines formed outside,” writes Angelo Biasi, a marketing expert, in a paper on viral branding.

The Black Dog Tavern at Martha’s Vineyard. (Photo: Dave Rezendes/flickr)

There’s a pretty stark divide between the humble, seafaring roots of Vineyard Haven and the current air of exclusivity and money of Martha’s Vineyard. It is very expensive to stay on the island: real estate is expensive to buy (“fixer-upper” ranch houses sell for upwards of $600,000), and the Vineyard has become a vacation spot for the wealthiest of coastal elites. Presidents Clinton and Obama have vacationed there. John F. Kennedy, Jr. crashed his plane and died there. And a t-shirt with a black dog on it costs, minimum, $26, and you used to have to wait in line to get it.

Starting in the mid-1990s, the Vineyard became deeply associated with wealth and casual preppy fashion.  Everyone who saw you clad in the Black Dog t-shirt would know that you had enough money to visit the island, but enough taste to go somewhere quirky and understated instead of choosing flashy Miami or Las Vegas. “The Black Dog is inextricably tied to its Vineyard origins, which make the brand an appendage, of sorts, of the island and its New England history and, yes, its bent toward affluence,” writes Jen Biasi, Angelo’s wife and the president of Smart Marketing Solutions. Perhaps nobody exemplified this more than President Bill Clinton, who during his presidency visited the Vineyard several times and was photographed wearing Black Dog merchandise.

And it was thanks to President Clinton that the Black Dog got a different kind of attention. The former president gave Black Dog gear to Monica Lewinsky, which means that the nautical tavern’s brand was discussed in the infamous Starr Report. From the report:

“Before the President had left for vacation, Ms. Lewinsky had sent a note asking if he could bring her a T-shirt from the Black Dog, a popular Vineyard restaurant. In early September, Ms. Currie gave several Black Dog items to Ms. Lewinsky. In an email message to Catherine Davis, Ms. Lewinsky wrote: “Well, I found out from Betty yesterday that he not only brought me a t-shirt, he got me 2 t-shirts, a hat and a dress!!!! Even though he’s a big schmuck, that is surprisingly sweet – even that he remembered!”

When I suggested that, on the mainland’s Northeast coast, the Black Dog signifies laid-back wealth, Gardella laughed. “I think that’s an interesting perspective, especially since the Black Dog t-shirt is a pretty affordable item,” she said. The shirt, though, had become a kind of dog whistle for those who recognized the simple design, a subtle way to mark yourself as part of the Vineyard tribe, much to the horror of longtime residents. “Seeing one was like how to pick who was not from here,” an island carpenter told the New York Times in 2002.

Now, though, there is another way of establishing bonafides. Gardella says wearing old, tattered, original Black Dog gear is a sign that you’ve been on the island for a long time. “The more modern stuff is definitely a lure for visitors,” she says.