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One morning last month, the ferry from Hyannis, Mass., to Nantucket Island carried sun-hatted tourists, seasonal laborers and two young blond British women who were three weeks into what was quite possibly the best summer of their lives.

Fee Meynell and Ella Crockett plopped their bags down for the one-and-a-half-hour ride. Ms. Meynell, 23, was lively and talkative. Ms. Crockett, 21, was conserving her energy, having recently spent four days sick in bed. “I’m very fragile,” she said, slumping over a table.

Ms. Meynell and Ms. Crockett are “Seasonnaires,” the term the British clothing company Jack Wills uses for its summertime brand ambassadors. They had been chosen from 3,000 applicants and sent to live for two months in a location with a Jack Wills shop; for Ms. Crockett, it was Nantucket, for Ms. Meynell, Martha’s Vineyard.

“When I applied, it was a pipe dream,” Ms. Meynell said. “You never expect to get it, do you?”

She recalled that as a teenager she had a poster in her bedroom of Jack Wills Seasonnaires jumping up and down in front of a lighthouse. Her relationship with “Jack,” as she called the brand, had been “very fan-girly.”

“I probably took it quite far,” she said. “I’d go out in Jack Wills pajamas.”

Jack Wills is still little-known in America, one of those preppyish brands like Vineyard Vines or Kiel James Patrick that’s a shared secret among the boat-shoe crowd from Annapolis, Md., to Kennebunkport, Me.

But in Britain, it has been popular for years. At the suburban London high school that Ms. Meynell attended, the cool kids wore Jack Wills hoodies, crews and chinos. “If you didn’t have Jack, you were no one,” she said.

Ms. Crockett, who also grew up in suburban London and has modeled for Jack Wills, nodded in agreement, saying: “At my school, you put your lunch in a blue-and-pink Jack Wills bag. You wanted the bedding. You wanted the knickers. You were obsessed.”

Both remembered fawning over the brand’s catalogs, which, similar to those of Abercrombie & Fitch, feature attractive young men and women cavorting at sporting events or falling into bed in their underwear, post-pillow fight. (The sexualized imagery in the spring 2016 catalog — and its winking promotional copy about “midnight mischief” — led it to be banned by the Advertising Standards Authority, a British media watchdog.)

On the ferry ride, both women wore the brand they have been relentlessly promoting. Ms. Meynell had on the red Bagley shorts and a white Eccleston T-shirt, while Ms. Crockett was dressed in black Fernham high-waisted jeans and the Hoyle tank. Her overnight things were stuffed into an on-brand blue-and-pink duffel bag.

They were returning after a night in Chatham, a town on Cape Cod that also has a Jack Wills store.

Three weeks into their branded summer, the women were still adjusting to New England, which neither had ever visited before, and to their out-every-night social schedule, in keeping with the corporate hashtag mantra to #livelifelouder.

“Mealtime is not a thing when you’re a Seasonnaire,” Ms. Meynell said. “I eat at 2 a.m. when I get home.”

And the partying and brand promotion doesn’t end at the bar. “We have so much alcohol in the house,” Ms. Crockett said.

College Life Forever

When Ms. Meynell and Ms. Crockett were selected for the Seasonnaire program, they were sent for training at Jack Wills’s London headquarters, where they met with the co-founder and chief executive, Pete Williams.

Now 42, Mr. Williams, who is British, started the brand at 24, an age when he had already realized, he said, that his best years were behind him. Jack Wills was about capturing (or recapturing) the rush of college and post-college youth.

“You have all the amazing independence of being an adult, but haven’t lost the naïveté,” Mr. Williams said from Britain by phone. “You don’t have a boss, a wife or husband, kids or a mortgage and the responsibilities that grind us all down. That spirit is intoxicating, and you don’t realize it until later.”

Founded in 1999, the brand’s visual and spiritual DNA comes from Salcombe, a preppy nautical resort town in southwest England similar to Nantucket that Mr. Williams once visited with a college girlfriend. As for the term Seasonnaire, it’s based on a tradition in Europe in which students would take a gap year between high school and college and go work at, say, a ski resort in the French Alps.

“It was an amazing time in your life, lots of fun working and partying,” Mr. Williams said.

The job of a Jack Wills Seasonnaire, as Ms. Crockett and Ms. Meynell learned, involves going out to bars, beaches and restaurants, meeting lots of people and spreading the word about Jack in the friendliest, most organic way possible. So far, in an expansion push into America begun in 2010, the brand has opened stores in wealthy enclaves and university towns on the East Coast like Westport, Conn., and Boston. Seasonnaires also work in the stores and organize promotional parties like the Croquet and Cocktails event that was held at the Chatham Bars Inn.

Being a Seasonnaire is a pretty good gig. The company pays their room and board, allowed them to go on a shopping spree at its Boston location and puts them up at houses set aside for Jack Wills employees.

They get around in vintage Land Rovers, or “Landies,” as the women called them, painted in the company colors, blue and pink. They also have expense accounts to go with salaries they would not disclose.

Both Ms. Meynell and Ms. Crockett were paired for the summer with male American counterparts who share the rental houses and job responsibilities. Splashing in the waves, sipping champagne on yachts, having sunset dinner parties right on the beach: A Seasonnaire’s life is like a catalog shoot come to life.

Mr. Williams encourages the young people he ships off to what he called “emotionally rich locations” in America to say yes to everything. During their orientation in London, Ms. Meynell and Ms. Crockett heard the legend of Red Rainey, a Nantucket-based Seasonnaire of a few summers back who had made a name for himself in company lore as a nonstop party animal, always up for anything.

“I remember Pete said, ‘Be like Red,’” Ms. Crockett recalled.

Mr. Williams sounded as if he wouldn’t mind trading places with the Seasonnaires in his employ. “They make me jealous, actually,” he said. “I try to live my life vicariously through them.”

‘Knackered’ on the Vineyard

By early August, Ms. Meynell and Ms. Crockett had each compiled a personal highlight reel of good times: a blur of boat trips, barhopping, late-night conversations with strangers and fast friends and sunbaked days patrolling the islands in the Landies.

Ms. Meynell and her American counterpart, Sean Fegan, started a biweekly Jack Wills party at the Loft, a club on Martha’s Vineyard. One night she danced until 1:30 a.m., then invited everyone back to the rental house for pizza.

“It got to 5 a.m. and we said, ‘Should we get a cab to the beach and watch the sunrise?’” Ms. Meynell said. “We climbed one of those lifeguard stands and watched the sun come up.”

“We went to bed feeling very knackered,” she said, using a British term for exhausted.

In Nantucket, Jack Wills sponsors a dance party on Mondays at the Chicken Box, where on a recent night Ms. Crockett stood on stage laughing as she tossed preppy merchandise into the crowd as if tossing chum to sharks.

“It’s literally like I’ve got a million dollars in my hand,” she said. “It’s ridiculous.”

The Seasonnaires are either embraced or derided on Nantucket and Martha’s Vineyard, depending on one’s age and tolerance for red Solo cups. It’s not uncommon for Ms. Meynell to meet people, she said, who have been partying in the house where she is staying, or even in her bedroom, during previous summers. Ms. Crockett, meanwhile, was convinced that the Nantucket police see the blue-and-pink Landy coming a mile away and get their summons books ready.

She was making quite an impression herself; Ms. Meynell said “the sushi guy” at a Nantucket restaurant they frequented had a crush on Ms. Crockett.

Despite ample suitors, both women said they had not entered into a summer romance. The main man in their lives, it seems, was Jack.

For part of her time on Nantucket, Ms. Crockett had worked without her Seasonnaire partner, Jon Wormser, who had to go home for family reasons. Ms. Meynell regularly took the ferry over from the Vineyard to help out; for instance, during the Monday parties at the Chicken Box.

Mr. Fegan, a muscled surfer with long hair and a friendly Labradorish manner, has been Ms. Meynell’s steady partner on the Vineyard, helping plan a dinner party one Saturday and translating American slang for her.

Mr. Fegan, a Maryland native with only passing knowledge of Jack Wills before this summer, theorized that he was picked partly because he attends college in North Carolina. Like a seed pod, he would spread the brand to the South.

Mr. Fegan was heading into his senior year in the fall, vaguely dreading it.

“I’m 22,” he said. “Sadly, I don’t want to graduate.”

The culmination of the summer for the Seasonnaires, as well as for many other people on the islands, is the yacht-themed festivities held in mid-August on Martha’s Vineyard and Nantucket. On a recent afternoon, Ms. Meynell and Ms. Crockett were busy planning the Jack Wills tie-ins.

At the end of the month, Ms. Crockett planned to visit New York before returning to Britain and her senior year of college. Ms. Meynell’s Seasonnaire experience was more bittersweet: It marked a goodbye to carefree summers. Having already graduated from college in June, she will return to London to a new apartment and her first adult job.

“When I’m older and have children I can say, ‘O.K., this summer, my last summer, I did this,’” Ms. Meynell said. “‘I have said yes to everything, lived up to that, pushed my boundaries.’”

She’ll also be flying home with bags of Jack Wills clothes bought with her earnings.