Annapolis is taking the fashion industry by storm.


Cheshire High School graduate Sarah Annapoli found post-pandemic success with casual women’s resort wear from her brand Sarah Joy.

Annapolis built her brand around positivity and color, personally designing all the patterns on her clothes. Following the pandemic, with more people looking to go on holiday, her home business has been a huge success, with her line now being carried by Bloomingdales.

A 2004 graduate of CHS, he attended the Annapolis College of Art and Professional Design and worked at the Manhattan Garment Center for more than a decade. In the year After being fired in 2019 and needing to support her 7-month-old son, Annapolis spent her summer brainstorming ideas for a fashion company to fuel her artistic interests.

Annapolis has always been interested in fashion, wearing the best clothes of her senior class. She took her art classes in AP art and translated her passion for the medium into painting. She explained that one of her works hung in the high school guidance counselor’s office for many years.

Choosing to combine both of her skills into her new business venture, Annapolis founded Sarah Joy.

Dressing well is part of what makes Annapoli feel positive and creative in her life, and she wanted to bring that same mindset to how she made her pieces.

“I was always into fashion. “I like to say, I’ve always been an artist since I was born,” Annapoli says, “Some of my friends used to call me a Hallmark card because I always had happy quotes.” When my son was born, I went through postpartum depression and had to dig deep and learn the tools, how to handle it all, new motherhood and the mental weight of it all.

“One of the ways I find this joy is through dressing and it’s a form of self-expression. I like to call it dopamine dressing, when you put on clothes and it makes you feel good inside,” Annapoli explains. “So the whole inspiration of the brand and what I do is to choose happiness and promote positivity in others, even in difficult and chaotic times.”

She had problems starting her new job. When it started production on its first production line in India, the factory was shut down at the beginning of the outbreak of Covid.

Despite the setback, Annapolis is still determined to spread the word about her brand and is pushing forward, choosing to make tie-dye masks and coloring books with her designs, as well as hosting virtual art parties on Zoom where people can paint and connect with each other. Despite the distance.

“To travel to promote the brand, to go to Miami for a photo shoot, I had all these huge plans that were impossible at first. But what’s amazing is that it’s turned into such a local community effort and growth and follow-up,” Annapolin said. “There are some strange blessings to that period, I was able to do a lot because I was home all the time. Which sounds kind of crazy, but I believe it has given me the opportunity to fully immerse myself in what I do.

Living in Cheshire and growing up at school helped her develop her artistic talent. Annapolis is able to express her experiences and self-expression in AP Art, allowing her creativity to flourish.

“It’s a beautiful thing to see that persistence and tenacity,” said Pamela Pekerman, founder of Hustle Like a Mom, an entrepreneurial group dedicated to helping mom-started small businesses grow their success. Pekerman met Annapoli at a networking event and helped her start her business after being inspired by Annapoli’s clothing styles.

One of the strengths of Annapoli’s line is not only her designs, but she also makes her own fabrics for the costumes, Pekerman said.

“I thought it was an amazing story to tell because it was so unique. They’re buying fabric at the market for the paintings, yes, but she’s really an artist who puts her finger on fabric in a way that others don’t. And I was angry about that,” Pekerman said. She brings so much energy and joy and tenacity that anyone looking for inspiration will have that to take away.

According to Pekerman, mother-run small businesses have been on the rise since the pandemic, and the success of Annapolis’ innovation is an encouraging sign of future female-led entrepreneurship in many business sectors.

At the same time, Annapolis wants to continue to expand. Now a mother of two, she collaborated with other companies to create spray-painted New York jackets and painted pieces for the Fana Hotel in Miami.

“I hope to see more creative collaborations as I think they will help me find my niche and grow as a fashion designer and resort wear collection,” says Annapoli. “I’m very proud of what I’ve accomplished up to this point and I’m excited to share it with the world.”

More details about Sara Joy are available online at and on Instagram.


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