It was midafternoon in Barbados, and a tall gate swung open onto a wide yard. Lauren Austin led the way through her home-turned-costume-production factory, stepping around a dozen four-foot-tall wings, their fuchsia feathers stretching out across the floor.

On one side of the room, two members of her team wrapped padding around wire wing frames. On the veranda, another team member was spraying feathers with various colors, creating an ombré effect. Crop Over preparation was officially underway, and Ms. Austin, along with her team of 15, had more than 600 costumes in production.

The Crop Over festival in Barbados dates back to 1687, celebrating the end of the yearly sugar cane harvest. Formerly known as Harvest Home, the festival began on plantations across Barbados during the trans-Atlantic slave trade and was one of few times of the year when enslaved people could freely celebrate, dance and sing. Since 1983, Crop Over has been organized by the National Cultural Foundation of Barbados.

The festival lasts for three months, with parties, events and markets taking place throughout. It all leads up to Grand Kadooment Day, in which revelers dress in elaborate costumes and dance “on the road” along a dedicated route.

Those who participate in Crop Over can choose between many different “bands” — that is, design houses — to jump with, and they pay the band for various services, which can include a costume, food, drinks, security, mobile restrooms and goody bags. This was the first Crop Over festival since the coronavirus pandemic; the last was in 2019.

The costumes are a major highlight of the experience, and Crop Over style has influenced fashion on a global scale. Rihanna and Jourdan Dunn have worked with local designers to execute their elaborate festival looks, helping to solidify the signature style associated with Crop Over in the modern day.

Though many of the designers are men, women hold a firm place in the creation of the festival, which is steeped in history and culture. Whether they are carrying on a family legacy of design or are self-taught innovators, their creativity and vision is remarkable.

Here, five visionary women whose work is shaping Crop Over fashion now.

Lauren Austin

Founder and lead designer: the Aura Experience
How she describes her style: Vibrant and creative

Ms. Austin, who is self-taught, began designing in 2011. Aura is the second band she has founded, and she owned it from 2016 to 2019. “I left the band as owner because I was going to have my baby, Saphire-Ray, and I also wanted to focus on designing,” she said. Designing is her passion, and her keen eye for style has attracted many well-known clients, including Rihanna, Miguel and Beenie Man.

“Crop Over is so magical,” said Jalicia Nightengale, her lead model. “On the day itself, everyone is just so free up, everyone is so happy, and it’s a moment for us. It’s the main event.”

Ms. Austin’s theme this year is “City of Angels,” inspired by a friend of Ms. Austin’s who recently died, and will include an all-gold section of costumes as tribute.

Kathy-Ann Layne

Lead designer: Kontact Band
How she describes her style: Modern and sexy

When Ms. Layne’s great-uncle died, she moved in with her great-aunt to keep her from being alone. In the evenings, her great-aunt taught her to sew, which proved to be life-changing for her. “She was a dressmaker, and she dressed many brides,” Ms. Layne said. “She helped develop my love for sewing, and the strange thing is that she was actually legally blind at the time she was teaching me.”

Ms. Layne studied design in college, then spent time in Trinidad perfecting her design style. The only female designer on her team, she wants women of all sizes to feel confident and sexy on the road. It can take up to two months to create a costume.

“Living on an island, we don’t manufacture raw materials,” she said. “With all of the disruptions in the supply chain right now, we have had to do things a full month earlier than we normally would. We want to ensure that the customer gets exactly what they paid for.”

Alyssa Goddard

Founder, owner and lead designer: Cambria Costume and Design
How she describes her style: Nontraditional pieces that tell a story

Ms. Goddard grew up around fashion. Her grandmother was a seamstress, her mother produced costumes for several Crop Over bands, and her sisters modeled for various designers on the island. “I remember watching my grandmother get ready to go jump with the bands,” she said. “She would keep the costumes in her bedroom on the shelves. I really enjoyed seeing her get dressed and head down the road.”

Ms. Goddard’s fiancé, Caleb Straker, is the only wire bender in Barbados, which is significant because the wire framework is the foundation of the costumes’ signature wings. Many designers used to source frameworks from other countries, but as shipping costs and delays increased, they began looking for someone closer to home. Mr. Straker perfected a method of building the frames quickly.

“I enjoy seeing the end result,” he said. “When they leave here, they’re these plain frames, and then they become the costumes. To see them on the road and see people enjoying them is awesome.”

Kashera Lewis

Founder, owner and lead designer: Envy Mas
How she describes her style: Modern with a little bit of flair

Ms. Lewis, who founded Envy Mas in 2013, wants to make Crop Over accessible for everyone. “I realized that a lot of people could not participate because of the high cost of the costumes, the band experience and all that, so I tried to make it affordable but still fashionable,” she said.

Ms. Lewis doesn’t go in for elaborate stones and beads. “We do a nice monokini with a couple of feathers” she said. “This year, instead of doing feathers, we did acetone backpacks, and so far, I’m the first in Barbados to be doing it.”

Part of Envy Mas’s popularity is that it’s a family affair. Ms. Lewis’s mother, Betty Lewis, has cooked all of the food for the band since it started. She makes everything in her own kitchen, with the occasional helping hands of a friend or two. “Everybody that jumps with the band looks for my food,” she said. “They shout: ‘Mom! Mom!’ I make chicken, ham cutters, roti, lots of things.”

The team at Envy Mas is made up entirely of volunteers, each of whom gets a free costume. “Some people might want more glitz and glamour, but there are a lot that appreciate us,” Ms. Lewis said. “I love what I’m doing for the community and for the youth in Barbados.”