Vineyard fashion is often said to be an oxymoron. Barn glamour, beach chic, preppy with a tinge of hippie are frequently used to describe how Islanders dress. But while dress clogs, Muck Boots, a clean pair of jeans, cowboy boots and the reliable plaid shirt may all be staples in many Vineyard closets, a group of Vineyard fashion designers have set out to redefine what it means to dress with comfort, confidence and, above all, personal expression.

Beginning Monday, Sept. 17, and running through Saturday, Sept. 22, fashion designers and clothing stores will present their designs at the second annual Martha’s Vineyard Fashion Week. The series of events benefits Angel Flight Northeast, which provides free flights to people requiring medical care. During the week there will be runway shows, trunk shows, parties and even movies about fashion.

Chrysal Parrot sewing fashion
Chrysal Parrot of Demi Monde is known for her Victorian styles. — Ray Ewing

Noava Knight is preparing 10 designs to be shown next Saturday. “I’m really inspired by the Island . . . we have all these different ways people interact and styles that come together,” she said in an interview at her studio in Edgartown. “You never know what you’re going to see.”

Ms. Knight manages the Chicken Alley Thrift Store in Vineyard Haven, and from this vantage point sees all manner of Vineyard’s fashion.

“The Thrift Store has more designer labels than any other store on the Island,” she said. “Designers like Helmut Lang — where else can you even get that [here]?”

Ms. Knight said she’s constantly inspired by the odds and ends coming through the door and only buys cloth from the spools of fabrics people have dropped off at what she called the “giant recycling center.” While folding used tablecloths one day, she came across a delicate lace Amish cloth.

“That started me on my theme this year, which is more romantic,” she said “In past years I’ve been a bit more funky, edgier, and now I have this elegant, red-carpet style.”

Ms. Knight admits her designs may not be the most wearable on the Island, where red carpet events are few and far between, but that’s okay with her.

“It’s about using your hands and making things,” she said. “I don’t want to be disconnected from what I do.”

Mannequin with hat in clothing store
Inside Demi Monde, if only mannequins could talk. — Ray Ewing

As long as you feel good in what you have on, she said, you’ll look good, no matter what.

“What I’ve found growing up here is that if you let it be, the Vineyard can be a very accepting place and accepting of all places and styles and cultures,” she said.

Sea.Love swimwear designer Ashley Chase feels a bathing suit is one of the most comfortable outfits.

“I’m always inspired by traveling,” she said. “I’ve seen so many different women on beaches around the world that you get a feel for their take on what they think is beautiful . . . everything from simplicity to elaborate fashion, you can pull what you want from that.”

Sea.Love swimwear was formerly Ulu Swimwear, founded in 2009, and has now merged with a luxury beachwear brand. Ms. Chase will begin doing major trade shows this winter. She has added new beachwear and cover ups to her collection this year, including a top you can wear five different ways.

“I’m trying to make my pieces more versatile and it’s probably because I do live in a bathing suit the majority of the time,” she said.

Hand-cut lace, beach dresses and tunics are all also new this year, designs which have “really turned me into a lifestyle brand rather than just swimwear,” Ms. Chase said, something that translates well to the Vineyard aesthetic. For her, a simple black dress and 10 pairs of cowboy boots go a long way.

“There’s a sense of practicality and sensibility here . . . we go to the beach all the time and then you could end up on someone’s farm at night,” she said. “However you dress, it’s important to bring your own character into it and have fun with it.”

The phrase “all dressed up and nowhere to go” comes to mind for many, Ms. Chase said.

“People here have such artistic minds that there is actually a really great fashion scene here,” she said. “Because we don’t have as much access to stores as other people, we become more creative.”

Ashley Chase in studio
Ashley Chase and her assistant at work in her Balinese studio. — Ashley Chase

Designer Chrysal Parrot agreed. She hopes more people will stop looking for an excuse to dress up and relish in the opportunity for self-expression.

“There are all these people on the Vineyard wishing that they could dress up more,” she said at her Vineyard Haven store, Demi Monde. “We can express ourselves in our style and wear something else besides Carhartts and Muck Boots and cutoffs.” That said, she did admit to purchasing a pair of the all-purpose boots at the Dumptique, a thrift shop at the West Tisbury dump.

“I really appreciate the fact that I can throw on a pair of sweatpants and go to the supermarket, but I would like to steer the Vineyard toward having more dress-up events and making that be okay,” she said.

Ms. Parrot is known for her Victorian and Eduardian recreation pieces, intricate and dazzling in their own right. But her collection for fashion week this year is “much more contemporary” with “fun hip party dresses, all the way up to gala event gowns.” She shows her collection on Monday.

“I want people to see the other side of me, that my work is wearable by women of all sizes and shapes. I really design for the female body, not for skinny models,” she said.

This winter she’ll begin to widen her reach off-Island through a new website and several trunk shows lined up in New York city.

Designer Noava Knight
Designer Noava Knight finds inspiration and materials at her day job at Chicken Alley thrift shop. — Ray Ewing

“Down the road I see my line going somewhere,” she said. “New York is where I keep gravitating toward. I see a lot more interaction there.” The Vineyard fashion scene is “very individualistic,” Ms. Parrot said. “Vineyard fashion is casual and I really don’t fit into that most of the time,” she said, but added “I really do appreciate the fact that my children can go to school in whatever they feel like putting on and there is no judgment based on their clothing.”

The one piece of advice she gives to people is “know your body type.”

“Have a realistic picture of what your positive and negative body qualities are and dress for that,” she said.

Like Ms. Parrot, stylist Michael Hunter urges his clients to embrace fashion on the Island.

“When I have clients who say, where am I going to wear that? I tell them State Road Restaurant on Thursday night for dinner— what’s the big deal?” he said. “Oh, but I have nowhere to wear any of this stuff. Well you better shake that —wear it to Cronig’s.”

When Mr. Hunter isn’t styling clients he runs his boutique PikNik, both in Edgartown and in Oak Bluffs. Mr. Hunter is most interested in the process of creating a look.

“My main objective is to entertain,” he said. “I always like telling stories, I like to illuminate the process of building a look . . . I hope to overlap each model with the next model, helping to complete the predecessor’s look but I’m also interested in the interaction between the two people. A hug or a kiss, the relationship that’s implied.”

Vineyard fashion pushes beyond “subcultures” that people frequently fall into, added Mr. Hunter.

“A lot of times it’s about decisions, conscious or unconscious,” he said. “I love wearing three different kinds of plaid . . . if I like certain fabrics and see some through line, that works for me.”

Mr. Hunter believes in complete looks, which frequently means adding a scarf or a hat (ladies, let your fellas wear the hat if he insists, Mr. Hunter said).

“Oh, and stay away from trends,” he added before turning to a customer. “Make your own.”

Martha’s Vineyard Fashion Week runs Sept. 17 through Sept. 22 with an opening party and fashion show at Dreamland in Oak Bluffs on Monday. For a full list of events and venues visit