THE WHOLE BACK STORY...
... ALL 234,000 MILES OF IT.
It all started with a beach wagon, a dream, and a trailer full of flip-flops. Our founder, Mike, left behind his medical device sales gig, picked up a street vendor permit in Falmouth, MA, and turned an old-school Grand Wagoneer into the ultimate mobile shop. Parked by the beach, feeding the meters, and meeting thousands of like-minded adventure seekers—Wears Woody was born.
THE FIRST 100 DAYS
A hundred summer days, thousands of flip-flops sold, and one big realization—this was just the beginning. Mike sketched up our now-iconic wagon logo, expanded into tees and hats, and hit the road with a vision that stretched far beyond Cape Cod.
GROWING BEYOND THE CAPE
Fueled by support from our growing crew of fans, Woody rolled out beyond the Cape, setting up shop at music festivals, sports tournaments, and events up and down the East Coast. The goal? To bring bold coastal style straight to the people, wherever the good times were happening.

AN "OLD-SCHOOL" APPROACH
BUILT IN SMALL BATCHES
Quality over quantity—that’s how we do things. We craft our gear in small batches, using the softest fabrics and boldest designs that stand out in a sea of sameness. Today, with nearly 100 pieces made right here in Boston, we’re bringing our signature “bold coastal style” to adventurers from coast to coast.
DRIVING OVER DIABETES
Mike has been thriving with Type 1 diabetes for 45 years, and our mission is bigger than just great apparel. We’re here to push the limits, inspire others to chase their wildest dreams, and give back along the way. A percentage of every sale goes toward finding a cure—because looking good and doing good should always go hand in hand.
WELCOME TO OUR WAGON
With 234,000 miles (and counting) on Woody’s wheels, this journey is far from over. Whether you’ve been with us from the start or are just hopping on board—welcome to the ride. Let’s go places.