Written by Jack Phillips
Edited by Jessica MacDougall
For Jess, running has always been more than miles; it’s her way of giving back. What started as a personal challenge quickly became a vehicle for purpose, a way to turn every race into something bigger than herself. “Running is where I find peace, but it’s also where I find meaning,” she says. “If I’m going to put in all those miles, I want them to matter.”
That purpose-driven mindset is what connected Jess with Wears Woody, a brand known for its coastal-inspired lifestyle and deep commitment to supporting Type 1 diabetes (T1D). But the way they met wasn’t planned; it happened the way all the best stories do: by chance.
“I was at my son’s lacrosse tournament, just hanging out between games,” Jess recalls with a laugh. “I saw the Wears Woody tent and had to check it out. I ended up talking to Mike, the founder, and jokingly asked, ‘So… Do you sponsor runners?’ He lit up instantly. Next thing I know, we’re talking about running for charity and how we could make something work.”
That spontaneous moment turned into a partnership built on shared values — resilience, purpose, and grit.
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“Running is where I find peace, but it’s also where I find meaning." Jessica MacDougall |
“I’ve always believed in running for something greater,” Jess says. “Wears Woody’s mission to give back… especially their support for T1D… felt so aligned with what I care about. They donate up to three percent of every sale to T1D causes, and that’s real impact. It’s not just words; they’re actually doing it.”
For Jess, that alignment came at the perfect time. She had been searching for a new way to make her miles matter and found that partnering with a cause-based brand opened doors she hadn’t imagined. “Because of this partnership, I’ve already been connected with a new charity, Kenyan Kids Foundation, and I’ve secured a bib for the Boston Marathon, one of the Abbott World Marathon Majors that’s almost impossible to get into. It feels like everything just clicked,” she says. “Now I just need to raise $10,000, $5,000 of which Wears Woody has committed to helping with!”
But beyond the logistics and sponsorships, what Jess values most is the why behind it all. “Running teaches you grit,” she says. “You’re out there for hours, fighting your own mind, your own limits. That same grit shows up in how you live. It truly makes a difference in how you parent, how you show up for others, and how you give back.”
Wears Woody’s community is built on that same mindset. The brand was founded on boldness; a belief that living with purpose and giving back go hand in hand. Whether it’s through American-made gear, road trips across the country, or raising awareness for T1D, their story is one of movement and mission.
Jess fits that story perfectly. She doesn’t see herself as an elite athlete or influencer. Jess says she is simply just a mom who loves to run, give back, and be part of something that matters.
“It’s funny,” she says. “I never set out to be a brand ambassador. I just loved what Wears Woody stood for. The fact that I get to represent a company that actually lives its values — that’s what keeps me excited to lace up.”
Her advice for others who want to make a difference through movement is simple: start where you are. “You don’t have to be a marathoner,” Jess says. “You just have to care, and find small wins to keep you going. When you align your passion with a purpose, you’ll be amazed by the opportunities that find you.”
For runners, athletes, and everyday adventurers who share that mindset, Wears Woody’s Athlete Ambassador Program is the perfect place to start. It’s more than just a partnership. It’s a community of people using their passions to make an impact. Because when grit meets purpose, every mile matters.