The Lasting Heritage of Oak Bluffs, Martha's Vineyard

      “The Vineyard is an incredibly sacred place,” remarks Áwet Woldegebriel, the founder of his namesake fashion label based in New York. Like many artists who reside on the island, Woldegebriel has returned every summer for nearly ten years, seldom being away for more than a few months. For many locals, this connection is equally profound. In his memoir, *I Regret Almost Everything*, renowned restaurateur Keith McNally recounts his first impressions of Martha's Vineyard while waiting for the ferry from mainland Massachusetts. “As I observed the Nantucket passengers disembark,” he mentions in the book, “I was turned off by their preppy, white appearance and favored the diverse group of passengers from the second boat: a mix of farmers, dropouts, and long-haired academics… I quickly changed my ticket.” Located just 28 miles across the Nantucket Sound from its neighboring island, Martha’s Vineyard has maintained its status as the opposite of the wealth, lineage, and exclusivity that characterize Nantucket—its residents are dedicated to preserving this difference. The island's working-class beginnings are not its only distinguishing factor. More than any other resort area on the East Coast, Martha’s Vineyard boasts a rich and intricate heritage, deeply intertwined with Black history.

      "It's not solely about beautiful beaches and scenic views,” Woldegebriel expresses. “It’s a space filled with creativity and resilience. This legacy, alongside a profound sense of community, is what draws me back. It’s one of the rare places where you can feel completely comfortable and also connected to a larger narrative.” While the island is often recognized for the charming white picket fences and bright hydrangeas of Edgartown, as well as the A-list neighborhood in Chilmark where the Obamas spent summers, it’s the town of Oak Bluffs on the northeast shore that, according to Woldegebriel, “has consistently been a heartbeat for Black joy, culture, and gathering.” Today, Oak Bluffs is a cherished destination for family vacations and community events, but its history as a sanctuary for Black travelers dates back to the Civil War era when the island was part of the Underground Railroad. During the peak of Jim Crow laws, places like the Dragonfly House in Oak Bluffs, which is now a community center, were recognized as safe havens for Black travelers in the Green Book. Consequently, many notable figures have visited its shores—from poet Langston Hughes to Gabrielle Union and Dwyane Wade.

      This summer, Ralph Lauren is highlighting this coastal destination with the introduction of a limited-edition collection and campaign showcasing the story of Oak Bluffs. “This collection transcends a picturesque coastal town; it’s a tale of the American dream," explains Ralph Lauren, executive chairman and chief creative officer of Ralph Lauren Corporation. “The unique history, traditions, and sense of community in Oak Bluffs profoundly inspire me and reflect what we all seek—a place where you can be free, authentic, joyful, and truly feel at home.” The Polo Ralph Lauren for Oak Bluffs collection embodies the East Coast spirit of the island, featuring iconic baseball hats, classic striped knits, and vacation-ready sundresses that resonate with both long-term residents and visitors.

      Woldegebriel agrees, stating, "There has been a renewed vitality in recent years." He notes the increased attention from national media, more investment in preserving its legacy, and enhanced storytelling about its history, asserting that while the island’s charm remains intact, there is a growing recognition of its cultural significance that is elevating Oak Bluffs and Martha's Vineyard to a broader platform. Regarding the factors driving this change, Woldegebriel emphasizes that it all relates to increased discussions about diversity and heritage. “Oak Bluffs presents an authentic narrative that cannot be fabricated: a dynamic community with deep generational ties to Black excellence, style, and leisure.” When asked about places to visit once on the island, Woldegebriel suggests his favorite spots include The Dragonfly House, where he has hosted the annual Summer Bazaar for his label. He also recommends exploring Circuit Avenue for its blend of historic charm and local businesses, and enjoying a seat on the Inkwell Beach seawall at sunrise or sunset as essential parts of his itinerary.

      **Shop the Collection**

      Polo Ralph Lauren

      The Oak Bluffs Track Jacket

      Polo Ralph Lauren

      The Oak Bluffs Striped Jersey Shirt

      Polo Ralph Lauren

      The Spelman College Twill Ball Cap

      Polo Ralph Lauren

      The Oak Bluffs Patchwork Jacket

      Polo Ralph Lauren

      The Spelman College Wrap Dress

      Polo Ralph Lauren

      The Oak Bluffs Baseball Tee