The Black Dog T-Shirt

MUST HAVES  |  SHIRTS  |  The Black Dog T-Shirt

There's something about The Black Dog Tavern in Vineyard Haven... Despite its overwhelming popularity with tourists and the increasing commercialisation of the brand (think Planet Hollywood but not as tacky), it is still a preppy classic and is known for the chowder and the t-shirts. I always find myself there for a drink if nothing else when on The Vineyard and still wear my The Black Dog t-shirts for a tongue-in-cheek casual look.

Preppies rue the day that celebrities started donning these t-shirts in the 1990s and ruining their little treasure (similar to the celebritisation of The Hamptons). The t-shirts were made even more famous as Bill Clinton used to give them as gifts to Monica Lewinsky during their scandalous affair.

Back in the day, people would queue outside the Vineyard Haven tavern for ages to get a table at The Black Dog and to buy one of these t-shirts. Despite the fact that these t-shirts can now be purchased online or at one of the various The Black Dog locations around the Northeast and Mid-Atlantic, I still reckon the t-shirt is a preppy Must Have.