On Saturday, Cynthia Rowley staged her brand’s 101st runway show this New York Fashion Week season against the backdrop of the newly renovated Wagner Park, with sailboats circling the tip of Manhattan and the Statue of Liberty in view. The collection featured the designer’s signature “pretty meets sporty” aesthetic, with reimagined windbreakers and running shorts shown alongside fluid dresses. For the first time, the runway also included men’s looks, with TikTok star “Henry” (@henryhenryhenryhenryhenryhenr) among the models and an appearance by Rowley’s daughter, creator Kit Keenan, who walked the show in a “sexy little dress,” as Rowley described it.
Even though Rowley had once promised herself she would not show outdoors again, she said the setting was too good to resist. “It actually seats 900 people, and we custom-made 10 sails for sailboats. So we had sailboats sailing around right in front of where the girls were walking,” she said. “We opened the show with a boy, which I thought was fun, because a lot of our pieces are things guys wear, too.”
“We’re an intergenerational brand,” Rowley added. “I love that it’s guys, girls, people who’ve been wearing the clothes since the ’90s and then people just discovering us now. It feels very free and joyful.” Longtime Rowley muse and model Leilani Bishop, returned to the runway, having first walked for the designer in 1994. “She’s more gorgeous than ever,” Rowley said. “We surf together all the time, and it felt right to bring back friends who’ve been part of the brand since the beginning.”
Ahead of the show, Rowley staged a social-first stunt called #ShowUsYourWalk, where fans were invited to post themselves strutting in Rowley pieces for a chance to be featured. The activation mirrored the playful spirit of the brand and extended the runway experience beyond Wagner Park.
Keenan has become a key conduit for introducing Cynthia Rowley to younger audiences. With 418,000 Instagram followers and 322,000 TikTok followers, she uses her platforms to post outfit inspiration, lifestyle content and viral snack recipes. On creator-commerce app LTK, where she has 28,000 followers, her posts range from “fall outfits” to cooking series complete with affiliate links to Cynthia Rowley designs. Together with her mother, she hosted a giveaway for fans to win tickets to the show and a personal styling session, a move Rowley said was “really successful” in boosting engagement and awareness.
Rowley herself has leaned into social, with 31,600 followers on TikTok, where she posts behind-the-scenes content, styling hacks and team-led videos. TikTok was also a model casting factor: While capturing his show experience, creator Henry, with 663,000 followers, introduced audience of food and culture fans into the brand’s orbit.
Alongside Keenan and Henry, Rowley has built a network of micro-influencers with strong engagement, particularly in Montauk and New York City, where the brand remains focused. Figures like Eden Masliah (498,000 Instagram followers), Gabrielle Britez (216,000), Erin Harper (13,600), Sasha Herman (3,400) and Allie DePinto (9,700) have been dressed in Rowley’s pieces and featured at activations like the Cynthia Rowley surf camp, which the brand has run once a week every summer since 2020. Even Pancho the Diva, a dachshund with 137,000 Instagram followers, has worn Rowley gear, extending the brand’s reach into playful viral territory. Collectively, this ecosystem of Keeenan, Henry, Rowley herself and the brand’s supporting influencer network surpasses 2.3 million followers.
Rowley’s own style often contrasts with her daughter’s. “My daughters are more conservative than I am,” she said with a laugh. “They dress more ladylike, and sometimes I dress like a 15-year-old boy. I’m always experimenting with things that haven’t been done.” That curiosity has informed the brand’s direction for decades. “That mix of sporty and pretty is always the kickoff for the creative process. What are the pieces that are almost like activewear, and how can you elevate them and style them with something unexpected?”
Beyond the runway, Rowley has steered her company through a period of transformation. In 2020, the brand shifted away from seasonal collections toward an ongoing drop model. “We design, make and ship every day,” she said. “We have drops multiple times a week. We make smaller quantities that sell out, and then we replenish or reimagine. That has helped us grow in a controlled and robust way.”
Today, Rowley estimates that about 80% of sales are direct-to-consumer, e-commerce or through drop-ship partnerships, with the other 20% being wholesale. “Traditional wholesale is less of a focus for us,” she said. “We’ve switched to partnerships, collaborations and licenses. That way, we can infuse newness into categories we might not have the expertise in, while combining audiences.”
That approach fueled a string of recent collaborations. In June 2025, Rowley partnered with Pottery Barn on a colorful home collection of tabletop and decor. The following month, she released a limited-edition travel capsule with State Bags, transforming its playful silhouettes with her “pretty-meets-sporty” aesthetic. And in August 2025, she announced a tie-up with Airbnb Experiences, offering guests an inside look at her TriBeCa studio across three dates in September and October, complete with a Q&A, styling session and private shopping. Together, the partnerships reflect Rowley’s strategy of extending her brand into new categories while keeping design at the core.
Her retail strategy has leaned on testing new markets through trunk shows, often leading to store openings in smaller towns. “I did two trunk shows in the northern suburbs of Chicago, and they were so great that we’re now opening a store there,” Rowley said. She has also embraced storytelling in her stores, encouraging customers to wear archival pieces and celebrate the memories attached to clothing. “Sometimes someone has something from years ago and then gives it to their daughter, who shows up wearing it,” she said. “That’s cool storytelling, and it shows how the brand lives on.”
Amazon remains part of the business, though Rowley is mindful of balancing it with other channels. “It’s definitely a valid retail space that people should take seriously,” she said. Amazon Luxury Stores has increasingly courted names from Oscar de la Renta and Altuzarra, starting in 2024. Saks Fifth Avenue’s April 2025 launch brought Dolce & Gabbana and Balmain to the platform. For Rowley, the focus is on elevating her storefront and making Amazon work in tandem with her DTC.
She said her brand is now an eight-figure business, underscoring the strength of her pivot to drops, collaborations and omni-channel retail.
The CFDA will honor Rowley this season with the Founder’s Award in honor of Eleanor Lambert, a recognition of her influence and adaptability. For Rowley, the award reflects her ability to balance experimentation with longevity. “I never felt like there were boundaries,” she said. “I just wanted to make things, to have ideas and try them out.”
