Bluffs-Esque

Written by Natasha Bearden

August 2, 2026

Updated August 3, 2026 / By Natasha Bearden

One of my photographer friends reached out to see if I wanted to do a tennis themed photoshoot in response to the criticism tennis players were getting regarding their fashion choices. As a person who played tennis competitively in high school and plays recreationally now, I couldn’t say no. My friend recommended I wear pieces that I posted to my IG story, showcasing a sweater and hat with the words ‘Oak Bluffs’ written on it. My mom had a business trip in Boston and headed over to Oak Bluffs on Martha’s Vineyard. While there, she hit up a few gift shops and purchased a few goodies for me, including the sweater, hat, and few other items.

Photo by Ralph Lauren

Last summer, Ralph Lauren dropped their Oak Bluffs Collection as a way to honor Oak Bluffs on Martha’s Vineyard – a charming town where Black American professionals in the early 1900s vacationed and found respite. Back then when segregation was around, Black Americans were limited in places to travel and Oak Bluffs was the only town in Martha’s Vineyard that welcomed Black visitors. It turns out that Ralph Lauren was inspired by Bobby Garnett, a Black vintage curator from Boston. In addition to that, James Jeter was the main force behind this collection and is Ralph Lauren’s first Black Creative Director. As a Morehouse graduate, James helped shape Ralph Lauren’s collaborations with Morehouse and Spelman Colleges, two prestigious HBCUs (Historically Black College or University).

What makes Oak Bluffs unique are the clubs created by those who share a love of community and cultural legacy. One such club was the Oak Bluffs Tennis Club, which was established in 1959 by Black summer residents Gloria & Lincoln Pope Jr., Laura Hayling, and Lewis & Pat Downing. Every Labor Day Weekend, players, families, and spectators came together at Niantic Park so play tennis and socialize. Even though participation gradually declined in the 1990s, descendants of the founders have recently announced a revival of the club with the goal of restoring tournaments and youth programming while also introducing it to a new generation.

Even though it was quite warm outside, I couldn’t turn down this opportunity to put this preppy and coastal look together. The Oak Bluffs Collection not only featured classic coastal leisurewear, but also collegiate apparel. Even though my sweater may not be considered collegiate apparel, it still has similar features, mainly the large letters. I wore a short sleeve white collared shirt under that and white pants with a small slit.

Last summer while searching for Beanie Babies at Goodwill stores, I saw a vintage wooden tennis racket and decided to use that as a prop. For some texture, I brought a beige patent leather tote along with croc embossed loafers. Coastal preppy styles are usually minimal in jewelry, so I only wore a jade ring.

This shoot was very intentional and I’m so happy with how everything came together. The Oak Bluffs Collection by Ralph Lauren was not only about showcasing a timeless coastal style, but it was also tribute to the Martha’s Vineyard Black community whose history intertwines family tradition, HBCU pride, and cultural legacy.

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Hello! My name is Natasha and I'm passionate about discovering places near and far. Follow along for travel guides, photography, and lifestyle moments.

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