Models strutted through Stina Sayre’s Vineyard Haven shop, showing off her newest line, the Eden collection, during a Fashion Week event on a recent Thursday. At once form-fitting and figure flattering, the Eden collection, like all of Ms. Sayre’s clothing, is for powerful women who want to be both sexy and mysterious.

The following Saturday, Angela Sison of Conrado helped a customer tie the shoulder strap of a breezy cotton jumpsuit at the Chilmark Flea Market. Ms. Sison buys fabric during her travels and sells clothing under a tent in Chilmark during the summer.

Though both designers are at different stages of their careers, each has found a home on the Vineyard. Known for clambakes, oysters and summer sails, the Island also boasts a small but vital homegrown fashion scene. Here, designers are not boxed in by the vacation mentality that arrives in June. And while new talent tends to come and go with the summer season and the more established veterans set up shop, it’s clear that there’s room enough on this Island for all.

Ms. Sayre is well established on the Vineyard with shops in Vineyard Haven and Edgartown and a loyal customer base. She doesn’t focus on the resort crowd and her clothes fit in as well at an office in New York as they do at dinner on the harbor.

“I design for women who have a strong purpose in life,” she said. “I believe that clothing is your supporting actor.”

This season Ms. Sayre has added more vibrant colors into her staple pallet of grays and earth tones; she designs her clothes with fit, feel and flow in mind. She’s extremely fabric conscious, favors asymmetrical shapes and knows that showing less is sometimes suggesting more.

While her business is Vineyard born and bred, other established designers came to the Vineyard after building their business elsewhere. Trish Ginter of Frock built up her line in Connecticut after working in the fashion industry in New York. She came to the Vineyard last year, setting up shop on Beach Street Extension in Vineyard Haven. Her breezy dresses, skirts and shirts are simple shapes that she said are often bought for outdoor, rustic weddings.

“I did a white collection, and it’s really inspiring to look at them, they look so fresh,” she said, gesturing to a rack of dresses. White can be a hard sell, so Ms. Ginter has slowly begun dying the dresses new colors. But one thing at Frock never changes. “Simplicity all the way,” she said.

Designer Stina Sayre has been on the scene for over 25 years.
Anthony Esposito

Lorraine Parish, a former ballet dancer-turned-designer who has been a staple on the Vineyard fashion scene since the early 80s, built her career in New York City. And for her, New York is still essential for any designer. “My advice to anyone who wants to be a designer is get accounts in New York,” Ms. Parish said. “If you’re serious about what you do, that’s what you do.”

Like many other Island designers, Ms. Parish has learned to think outside the garment box. Her latest venture, Nurse Daisy, aims to bring sophisticated uniforms to medical professionals who want a designer’s edge. “A friend of mine was visiting her mother in a nursing home. She was wearing one of my jacket tops and all the nurses wanted it,” Ms. Parish said.

Travel is another way for designers to stay inspired. Many of the Island’s emerging designers split their time between Martha’s Vineyard and other locales. Liane Roy FitzGerald began Roy Swim, a comfortable, cheeky swimwear line after spending seven years as a lifeguard at Lucy Vincent Beach. She lived in a bikini and now aims to create two-piece suits that walk that ever-elusive line of style and comfort. Ms. FitzGerald sells at the Chilmark Flea in the summers and just expanded to her newest home-away-from-home, Santa Cruz, Calif.

“I tell everyone I don’t think I would have this business if it wasn’t started here,” she said. “Partially because there is money here to support handmade goods.”

And handmade goods are easy to be found at the Flea, where Roy Swim’s booth is just a few spots down from Conrado.

Angela Sison didn’t get her start on the Island, but she found her way here. Though this is her first full summer on the Vineyard, she’s been bringing Conrado here for three years, after being introduced to the Island by her boyfriend. Before creating her own line, Ms. Sison worked in the fashion industry in California, New York and Paris, and was a designer for Old Navy.

“I’m thinking about making [the Vineyard] one of my home bases,” she said. The community surrounding handmade fashion is a big draw for Ms. Sison, plus the Island fits her style of New England-meets-the-tropics.

And it’s not just clothes that benefit from the supportive Island community. The Vineyard jewelry scene has long been a thriving and dynamic draw for year-round and visiting shoppers, alike.

Frock's Trish Ginter makes custom alterations on the spot.
Jeanna Shepard

Elysha Roberts is perhaps a perfect example. She is a jeweler at the oldest jewelry store on the Island, CB Stark. Owner Cheryl Stark, a jewlery maker for decades, is currently celebrating her 50th year in business.

“We have a pretty amazing climate here, people looking for original designs, either Island related or not,” said store manager Sarah York. “The rich art community only benefits the amazing jewelry artists.”

Ms. Roberts began working at CB Stark after graduating from the Massachusetts College of Art and Design where she studied jewelry making. Now she also designs her own line, which is sold at CB Stark and Driftwood, in Oak Bluffs. Ms. Roberts said working at CB Stark helped her master traditional techniques that she can then apply to her own line as well. “I get to develop and grow more here,” she said.

While her individual metal work is sold at CB Stark, she sells her more abstract, artistic pieces made with paper, resin and leather at Driftwood, a boutique that specializes in showcasing local designers and up-and-coming talent. In addition to the support from the Vineyard, Ms. Roberts has found the Island to be full of inspiration. “A lot of my personal jewelry is based on the natural forms, organic forms and materials.”

Island jewelers like Ms. Roberts, Nettie Kent, and Stefanie Wolf are all familiar faces at festivals, outdoor markets and pop-up shops. Ms. York pointed to the early days, when CB Stark was one of the first booths at the Agricultural Fair. “There was nothing like the Chilmark Flea then,” she said. But the newest generation of designers has been raised to think local, relying on the Vineyard’s supportive community and the wide exposure it provides. After all, people from all over the world summer here.

“We reach a really wide audience here. We are able to test our items in a very diverse market,” said Noava Knight, creator of Humane Imperfections, a handmade luggage company. “And people see your work here that otherwise would never see it.”

Conrado's Angela Sison at the Chilmark Flea.
Anthony Esposito

But Ms. Knight knows that designers aren’t safe from the seasonal nature of the Vineyard’s economy. She focuses her business mostly on selling wholesale to local shops, but is now focusing her attention across the Sound.

“I’m working really hard to extend business off the Island in pursuit of a sustainable lifestyle,” she said. Her designs have expanded to include backpacks, duffle bags and oversized carry-ons that will stand out in the airport.

“I’m happy we have people in my age range giving it a shot,” Ms. Knight said of the crop of young designers she sees coming up beside her. “We have a good foundation of support. My roots are the people who have supported me here in my growth.” She counts among her mentors older Island designers, including Sylvie Farrington and Ms. Knight’s mother, who designed children’s clothing. “The soul of the Vineyard gets translated into the soul of design. It’s a really supportive place.”