above: Stocker (center left) uses fashion to bring the community together through initiatives like the Stamford Health fashion show (middle) and her collection with Ali Truwit (right), which benefits Truwit’s Stronger Than You Think, supporting women and girls with limb loss. – Photos: left and middle photos by Frances V. Issac Photography; ali and talia by Katharine Calderwood
Sail to Sable owner Jennifer Stocker teams up with local designers, athletes and entrepreneurs to create collaborations that benefit the brands and the community.
For Jennifer Stocker, community is at the heart of her business. After leaving the Manhattan publishing world, she returned to her hometown of Darien to launch Sail to Sable, a brand that has grown into both a thriving store and a platform for other women and emerging brands.
Today, Stocker uses the brand—and its Darien store, STS The Cabana—to bring together local women, artists, athletes, entrepreneurs and charitable organizations. Since opening the store in 2021, she has hosted events and launched collaborations that give other brands and creatives an opportunity to reach new audiences.
“Our Darien store has increasingly become more than just a place to shop,” says Stocker. “It is a place where we can host events, launch collaborations, bring our community together and personalize products.”
Stocker is deliberate about the partnerships she pursues, looking for collaborators who bring something distinctive to the brand. “We have been very intentional about making collaborations feel like a true combination of two brands rather than simply putting our names together,” she says.
Local Launch
HEY GRAY LADY
When Lizzy Walsh launched Hey Gray Lady from her Darien backyard, she turned to Stocker for advice as she built her jewelry business.
“Jen believed in my vision from the very beginning. Her guidance, encouragement and generous support gave me the confidence and foundation I needed to turn my idea into a business,” says Walsh. “I will always be grateful for the important role she played in helping me launch Hey Gray Lady.”
Today, Walsh’s coastal-inspired jewelry and linens collection is a regular presence at STS The Cabana. For the holidays, the two Darien entrepreneurs are expanding their partnership with new jewelry pieces featuring Hey Gray Lady’s signature starfish design, along with another new offering at The Cabana: in-house monogramming.
“This season, we’ll be launching an exclusive jewelry rounder featuring Hey Gray Lady’s signature starfish motif, which can be personalized with a monogram right at The Cabana,” says Stocker. “Your favorite Hey Gray Lady pieces can become a personalized keepsake.”
Stocker sees the new additions as part of what makes the Darien store different from shopping online.
“These offerings give customers another reason to come into the store and interact with a brand in a way they simply can’t online,” Stocker says. “We will incorporate monogramming into our existing assortment as well as create special embroidery moments around events, collaborations and holidays.”
All-American Style
CHLOE HUMPHREY
One of Sail to Sable’s recent partnerships is a distinctly Darien collaboration, bringing together two hometown talents: Stocker and lacrosse star Chloe Humphrey—a Darien High School graduate who now plays for the University of North Carolina, the reigning NCAA champions. Already a fan of the brand, Humphrey brought her love of lacrosse and connection to the sport to the partnership.
“We loved the idea of taking the traditional Sail to Sable aesthetic and giving it a youthful, sporty lacrosse twist,” Stocker says.
The resulting Chloe Humphrey x STS Collection, featuring blue-and-white lacrosse pajamas and a heart necklace, was such a success that the pair will launch a special-edition holiday lacrosse pajama set December 2.
“The response to Chloe’s collection has been amazing,” says Stocker. “It showed us how strongly our customer connects with the intersection of sport, fashion and tradition.”
For Humphrey, the collaboration has been both a creative outlet and a special opportunity to work with Stocker.
“I’ve been so lucky to work with her on our lacrosse pajamas, holiday pajamas and necklace collaborations, and through each one, I’ve seen how much she genuinely cares about supporting female athletes and bringing our ideas to life,” says Humphrey. “Jen is constantly looking for ways to lift other women up, and anyone who gets the opportunity to work with her is incredibly lucky.”
Connecticut Connection
DUDLEY STEPHENS
Another upcoming collaboration expands Stocker’s local circle. Sail to Sable is partnering with Fairfield County-based company Dudley Stephens, best known for its elevated fleece, outerwear and layering pieces.
The holiday launch will include two Dudley Stephens styles rendered in a classic Sail to Sable print. The two female-run companies also share a similar customer base, making the collaboration, in Stocker’s words, “a natural partnership.”
The women who wear both brands “are busy, social and active, but they still want to feel pulled together,” Stocker says. “Sail to Sable is known for color, print and classic silhouettes, so bringing those two design languages together has been really fun.”
Dudley Stephens also recently teamed up with Penny Linn Designs, the contemporary Rowayton-based needlepoint company, on another local collaboration, creating two custom needlepoint canvases—one featuring an iconic Dudley Stephens fleece and the other showcasing the DS logo. It’s another example of the creative cross-pollination taking place among local brands and businesses.
Shared Circles
SAM BALL
The network of women supporting and collaborating with one another has grown around Darien and Sail to Sable. One example is Sam Ball, a 2018 graduate of Darien High School whose work has taken her from designing hand-painted Vans and champagne bottles to murals, custom pieces and collaborations with national brands including LoveShackFancy, SoulCycle and Roller Rabbit.
Ball’s connection to Stocker and Sail to Sable has grown through collaborations with other local women. She made an in-store appearance at STS The Cabana as part of the Hey Gray Lady pop-up, where she personalized pieces for customers.
She later brought her custom artwork to The Pearl in Rowayton, painting tote bags at an event celebrating the launch of Sail to Sable’s collaboration with Isabella Giordano, the creator behind Stay Stacked.
“Both times I’ve worked with Sail to Sable, I’ve had the opportunity to collaborate with multiple women to create such fun and creative events,” says Ball. “I love being part of that kind of community and seeing how everyone’s talents can come together.”
A Cause to Champion
ALI TRUWIT
Not every partnership is about expanding the product line. Stocker joined forces with fellow Darien native and two-time Paralympic medalist Ali Truwit to support Stronger Than You Think’s mission of providing better access to prosthetics. Truwit, who lost her foot and part of her leg in a shark attack, founded Stronger Than You Think and is also a swimmer, advocate, model and speaker.
Truwit’s journey inspired a limited-edition assortment of pajamas and sweaters, but Stocker and her team wanted the project to accomplish something greater.
“Our collaboration with Ali Truwit is one of the most meaningful partnerships for Sail to Sable,” says Stocker. “Ali’s story of resilience and her work through Stronger Than You Think are incredibly inspiring, and we wanted the collaboration to be about much more than simply putting two names on a product.”
One hundred percent of net proceeds from the collection benefit Stronger Than You Think, which helps women and girls in need of prosthetics, supports water-safety initiatives and builds confidence through paralympic sports.
“I had a lot of fun partnering with Jen,” says Truwit. “I particularly appreciated the focus on inclusion as we got to model the clothing we designed alongside one of Stronger Than You Think’s incredible recipients, eight-year-old Talia.”
“Ali is such a bright light in our community, and it was an absolute honor to collaborate with her and support such an amazing cause,” says Stocker.
GIVING BACK
Stamford Health
Long before many of these collaborations became part of the Sail to Sable story, Stocker was using fashion to bring people together around a cause. She has worked with Stamford Health on its annual Fashion Show for more than a decade, and prior to that, she had her own meaningful experience with the hospital and its staff.
When Stocker was in second grade, her father suffered a health scare and was hospitalized for a prolonged period. Helping Stamford Health and the community that cared for her own family will always be a priority.
“We believe the most meaningful partnerships are rooted in genuine relationships with the communities that have supported us,” Stocker says. “Giving back has always been something we want to incorporate organically into Sail to Sable rather than treating it as something separate from the brand.”
The annual fashion show includes a Sail to Sable pop-up shopping experience, with proceeds over the years supporting the Bennett Cancer Center, NICU, nurses’ stations and other hospital programs and facilities.
For many of those who walk the runway, the event is also personal. They may be patients or survivors, family members or caregivers, giving the fashion show a connection to the cause that goes far beyond the runway.
“Being able to use fashion as a vehicle to gather people together, celebrate those stories, and give meaningful support back to an organization that does so much for our community is exactly how we hope philanthropy continues to live within the Sail to Sable brand,” she says.