Don’t worry, Michelle Obama certainly knows how to dress for the Vineyard

Michelle Obama’s recent headturning looks on Martha’s Vineyard remind us that she’s always known how it’s done.

If Michelle Obama is going to do one thing, it’s absolutely have that ish on. The former first lady popped out during multiple book events on Martha’s Vineyard this week, wearing not one but two different stunning looks that have set the internet ablaze.

The first look she shared in an Instagram post was a vibrant coral pink strapless dress with white heels, followed by a green-and-white striped Carolina Herrera halter dress with brown criss-cross heels. Her braids were pulled up into a high ponytail, cascading down her back.

There’s just one problem, she admitted, she may have been a bit overdressed for Martha’s Vineyard.

“This is dressed up [and] we don’t do this here. I don’t even wear shoes,” she quipped during the event, the Vineyard Gazette reported.

She wore the slightly elevated resortwear looks while, somewhat ironically, discussing her book “The Look,” which chronicles her style legacy as first lady. And here’s the thing: Mrs. Obama definitely knows how to dress for Martha’s Vineyard.

Martha’s Vineyard style puts the emphasis on leisure while remaining refined. It’s relaxed, a little preppy, and, depending on where you’re headed, just the right amount of bougie. Obama, who has been coming to the island with her family for nearly two decades, has given us plenty of examples of it over the years.

When most people think of Martha’s Vineyard fashion, summer whites, linen, nautical stripes, and a preppy, quiet luxury probably come to mind. Ralph Lauren put a distinctly Black spin on that aesthetic last summer with its Polo Ralph Lauren for Oak Bluffs collection, created in collaboration with Morehouse and Spelman colleges and inspired by generations of Black residents and vacationers on the island. It’s that, of course. But Vineyard style is also about looking good while being off duty. You’re on vacation, after all.

For Black people especially, that sense of ease has a real history behind it. Black sailors and laborers were part of the island’s early maritime history, and by the late 19th and early 20th centuries, Black vacationers, including teachers, civil servants, doctors, lawyers, and ministers, were making their way to Oak Bluffs. At a time when segregation dictated where Black people could live, travel, and vacation, Martha’s Vineyard became one of the places where Black families could come summer after summer, buy homes, build community, and, quite simply, relax.

That history has helped shape the vibe — and, yes, the style — ever since. You could run into the former first lady at the local dive bar or a storied filmmaker in a souvenir shop. A prominent judge and his family could be renting a house next to your friend’s week-long rental. So it doesn’t hurt to step out in your best resortwear. But it’s more than the pomp and circumstance and bougie stereotypes that have become attached to the Vineyard. The island’s history of Black working and middle-class people coming there to find refuge, enjoy themselves, and build something they could return to generation after generation is reflected the spirit of the style—relaxed enough for the beach, polished enough for wherever you might end up afterward. 

Obama has always fit right in. During the early years, her Vineyard style was more relaxed. We’re talking shorts and an orange tank at Lobsterville Beach in 2009, leggings with a Duro Olowu tunic for dinner in 2010, and a preppy Talbots sundress she wore to kick off the family vacation in 2013. The family always treated us to posh returns and departures on the White House lawn. Post-White House and amid a new sense of freedom, the former first lady has only gotten more on-brand. Last summer at the Martha’s Vineyard African American Film Festival, she stepped out in baggy mom jeans with a bronze tank top, a printed Ralph Lauren blouse, a Western belt, and caramel slingbacks. This summer, she’s giving us midi dresses, heels, boho braids, and a slightly more dressed-up take on Vineyard ease while literally promoting a book about what clothing has meant throughout her life.

And maybe that’s what makes her Vineyard style feel so, well, fitting. So much of Obama’s fashion story has been about what other people thought about her clothes, from the endless scrutiny of her bare arms to the designers she chose and what it all supposedly said about her as first lady. “The Look” has given her the chance to tell that story for herself. Meanwhile, Martha’s Vineyard has long given her a place where she doesn’t have to perform at all. She can wear the dress and the heels, or apparently, no shoes whatsoever.

“This place is magic to our family. I mean, it really is. It’s one of the few places where we can go and just be,” she said.