In 2015, two sisters co-founded Dudley Stephens; one worked with Gucci, Calvin Klein, other managed American Express VIP experiences; how their brand crossed $45 million in sales

Dudley Stephens was founded in 2015 by sisters Lauren Stephens and Kaki McGrath, alongside their mother, Bonnie Dudley. Lauren had worked in fashion and beauty public relations for brands including Gucci, Calvin Klein, and other big brands.

Kaki brought experience in loyalty marketing and operations, including work with American Express and Starwood. The idea came after their mother needed clothing that would work both on a boat and at a dinner after docking.

The sisters recognised a similar need among busy women, which was comfortable, versatile clothing that could transition between different occasions. They pitched the idea to their business-minded father and received a small family investment to launch it.

How did they launch it in 2015?

The sisters began by creating samples and designing their first product, the Cobble Hill turtleneck.

Starting small meant the company sometimes sold through its inventory quickly, leaving customers disappointed when products became unavailable. In the early days, they handled much of the work themselves, including customer service, product tagging and coordinating embroidery and manufacturing.

Both sisters were reportedly pregnant while managing the business during its early stages.

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How side hustle became a full-time business

Dudley Stephens reached profitability in 2018. That year, it became a six-figure business and the founders began paying themselves consistent salaries and hiring full-time employees.

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In 2019, the company outsourced its fulfillment operations. The brand later benefited from the pandemic-driven shift towards working from home, when demand for comfortable everyday clothing increased.

The founders said, according to Entrepreneur, that sales tripled during the early months of the pandemic. They also reported that sales had tripled year over year since 2019, according to the report.

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According to the company figures reported by Entrepreneur in 2024, more than $45 million cumulative sales were generated by the brand.