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Cheshire High Grad Finds Success with Homegrown Fashion Line

Cheshire High Grad Finds Success with Homegrown Fashion Line

Sara Annapolen posing in front of her art supplies while working from home. Contributed photo

May 25, 2023 05:57PM

CHESHIRE — Cheshire High School graduate Sara Annapolen has found success post-pandemic with her custom line of women’s resort wear from her brand Sara Joy.

Annapolen forged her brand around positivity and color, personally designing all the patterns on her clothing. Following the pandemic, with an influx of people looking to go on vacation, her homegrown business has seen a surge of success, with her line now being carried at Bloomingdales. 

A 2004 CHS graduate, Annapolen went to college for art and professional design and worked at a garment center in Manhattan for over a decade. After being laid off in 2019 following the closure of the business, and looking to support her seven-month-old child, Annapolen spent her summer brainstorming an idea for a fashion company as a way to tap into her artistic passions. 

Annapolen had long held an interest in fashion, being named the best dressed of her senior graduating class. She also translated her artistic works into paintings, having taken an AP art class and falling in love with the medium. One of her works actually hung inside the guidance counselor’s office at the high school for many years, she explained.

Opting to combine both of her skills into her new business venture, Annapolen founded Sara Joy. 

Dressing well is part of what makes Annapolen feel positive and creative in her life, and she wanted to bring that same mentality forward in how she designs her pieces. 

“I have always been into fashion. I like to say since I was born I have always been an artist,” Annapolen said. “Some of my friends used to call me like a Hallmark Card because I always had journals of happiness quotes. When my son was born, I  went through the experience of postpartum anxiety and I had to really dig deep and learn the tools, how to handle all of this, new motherhood, and the mental weight of everything.”

“One of my avenues of finding this happiness is getting dressed and it's a form of self-expression. I like to call it dopamine dressing, when you put on an item of clothing and it makes you feel so good inside,” Annapolen explained. “So the general inspiration for the brand and what I do is all about choosing joy and empowering positivity in others, even in tough chaotic times.”

Beginning her new venture had its difficulties. As she began production on her first line, which was being manufactured in India, the factory ended up being shut down during the initial spread of COVID-19. 

Despite the hurdle, Annapolen was still committed to spreading the word about her brand and pushed ahead, opting to make tie-dye masks and coloring books with her designs while also hosting virtual art parties over Zoom where people could color and connect with each other in spite of the distance. 

“I originally envisioned traveling to promote the brand, going to Miami for a photo shoot, all of these extravagant plans that couldn't happen. But what was amazing about it was that it turned into such a local community effort and growing a following,” Annapolen saidrr . “There are some strange blessings to that time that I was home all the time, so I was able to work so much. Which sort of sounds crazy, but I do believe that it gave me a chance to be fully immersed in what I'm doing.”

Living in Cheshire and growing up in the school system helped her foster her artistic talents. Annapolen cherishes the experiences she had in AP art and being able to express herself in a way that allowed her creativity to flourish. 

“It's just a beautiful thing, to see that resilience and perseverance,” said Pamela Pekerman, founder of the Hustle Like a Mom entrepreneurship group — a community based around helping grow the success of small businesses started by moms. Pekerman met Annapolen at a networking event and helped her launch her business after being inspired by Annapolen’s clothing styles.

One of the strengths of Annapolen’s line is not only her designs but that she also makes her own fabrics for the dresses as well, said Pekerman. 

“I thought that that was a remarkable story to tell because it was so unique, because nobody's out there doing that. They're in the market buying fabric for sketches that they've made, yes, but she actually is an artist who puts her finger on the fabric in a way that others aren't doing. And so I was blown away with that,” Pekerman said. “She brings so much energy and joy and resilience that there's going to be that takeaway for somebody who wants to be inspired.”

According to Pekerman, small businesses run by mothers are on the rise post-pandemic and the success of Annapolen’s venture is an encouraging sign for the future of woman-led entrepreneurship across many fields of business. 

Annapolen meanwhile wishes to continue to expand. Now a mother of two, she has collaborated with other companies to create spray-painted New York-themed jackets and painted pieces for the Faena Hotel in Miami. 

“I hope to see more of those artistic collaborations as I think that they'll help me find my niche and to grow as a fashion designer and with the resort wear collection,” Annapolen said. “I'm so proud of what I've accomplished up to this point and I'm really excited to share it with the world.“

Further details about Sara Joy can be found online at and on Instagram. 

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