All in a Day’s Work: Kate Day on Co-Founding Dovetail Workwear

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Dovetail Workwear, co-founded by Chewonki alumna Kate Day (Semester 2; Camp Staff ’93 and ’96; Trustee ’95-’99; Advisor ’05-’11), is a hardworking company that makes hardworking clothes for hardworking women. In doing so, the company is helping usher in a more inclusive vision for highly physical professions, like construction and agriculture. This paradigm shift has everything to do with Day’s experience at Chewonki, which instilled a deep appreciation for manual work during her most formative years. 

Kate Day (left) with Dovetail co-founders Sara DeLuca (right) and Kyle Begley (middle)

Day co-founded Dovetail Workwear in 2014 because she noticed her work clothes (Day operated a small landscape business at the time, Moxie and Moss) were consistently less rugged, practical, and well-fitting than her male counterparts. Her pants, for example, were missing pockets and had fake reinforcement panels, their billowing fit slowed her down, and they were often covered in girlish patterns, too. “I felt shortchanged by the implicit assumption that women aren’t working as hard as men,” she says.

Dovetail workwear is a hardworking company that makes hardworking clothes for hardworking women

Day and her business partner worked with a local designer in Portland, Oregon, to create the first pair of Dovetail work pants. They had just two pairs sewn, one for each of them, not realizing they were tapping into a huge, unmet desire for rugged and stylish workwear. They did little to market the pants beyond wearing them to work, yet the interest was remarkable. So the entrepreneurial pair, now a trio, seized the opportunity, founding Dovetail Workwear with the help of investment and business guidance from Portland Product Werks (with whom the company eventually merged). 

Transitioning from landscape design to the apparel industry was no easy feat, however, despite the excitement around Dovetail’s products. Day went from having a few dozen clients to thousands of customers and worrying less about dirty fingernails and more about global supply chains, sourcing raw goods, and sustainable production in the span of a few short years.

Day (right) with Dovetail workwear co-founder Kyle Begley (left). Before starting their workwear line, the pair co-owned a landscaping business called Moxie and Moss.

Good thing Day relishes a good challenge. She says she also benefited from being both an outsider and a woman in the male-dominated workwear industry. “It’s our superpower,” she says, “because we see things differently.” This fresh perspective, paired with Day’s determination and ingenuity, has been essential to the company’s early success. “We never had the money for a big marketing agency,” says Day, “we followed our instincts instead of the established rules.” 

Today, the company has ten full-time employees, a quickly expanding customer base, and Day is rocking and rolling from early morning PR meetings to late-night sample sales. The company’s ethos reflects Day’s Chewonki experience in many ways, including the all-hands-on-deck approach, emphasis on physical work, and community-minded attitude. “I don’t mind getting dirty, and so much of that comes from Chewonki,” she says, fondly recalling mucking stalls and morning farm chores. 

Day's Maine Coast Semester class photo

In addition to a stellar work ethic, Day says that Chewonki inspired a love for the natural world that has propelled many of her career choices. Before her foray into landscaping, she worked as a camp leader, farmer, arborist, construction worker, and ecological research assistant. Later, Day became a city planner, navigating the intersection of man-made landscapes and the natural environment. 

It’s also worth noting that Day attended Maine Coast Semester when it was just a fledgling program; we had been welcoming students for less than six months at the time. Day’s class helped build the program in both a literal and metaphorical sense. “Having that agency when I was so young felt incredibly empowering,” she says. It’s easy to see the connection between this early, formative experience and Day’s lifelong commitment to the messy, inventive work of building meaningful, community-minded enterprises.

Maine Coast Semester is well known for it's work program and daily farm chores

As Dovetail Workwear grows, Day finds herself grappling with a new challenge- namely, how to maintain the unique company culture she’s worked so hard to cultivate. “It’s exciting to think about growing, and it feels scary, too,” says Day, “ if we get too big, then people and departments can get isolated or siloed.” So she is working hard to set the stage for a larger business. “Everything we’re doing right now will set the tone for who wants to be part of this business moving forward,” she explains.

It’s exciting to consider all the possibilities that Day and Dovetail Workwear have ahead of them. And, although much uncertainty lies before them, we are 100% sure that Day and her team will have the quality workwear they need to build something great–perhaps transformative. That’s what it’s all about, after all. 

Learn more about Kate Day and Dovetail Workwear.

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