It's Back! Sebago revives the Docksides ‘Gary Jobson’
The Portland Gary Jobson is more than a shoe—it’s a tribute to freedom, heritage, and life on the water. Originally crafted in the 1980s to honor the legendary American sailor, this reimagined classic carries forward the spirit of adventure with a sleek, modern edge. With hand-stitched detailing, side laces, and a custom sole that nods to Gary Jobson himself, it’s a timeless icon for those who embrace the call of the ocean.
“Stability on a racing or cruising boat is essential for sailing swiftly and keeping a crew working efficiently. All boats are in constant motion and often wet creating slippery decks and challenging sailors to stay on board. Over the past 50 years of racing I’ve relied on Sebago shoes to keep me on board and sailing at a high level. Plus my Sebago’s always look good around the docks.”
Gary Jobson - Brown
$195.00
Gary Jobson Suede - Brown Cathay
$195.00
Gary Jobson Suede - Grey Taupe
$195.00
Back in the ’80s, Sebago teamed up with world-class sailor Gary Jobson—an America’s Cup champion, TV commentator, and all-around legend of the sea—to design a boat shoe worthy of his name. The result? A laid-back classic that sailors and landlubbers alike could appreciate. The Gary Jobson became a quiet cult favorite, and now it’s making a comeback as the Portland Gary Jobson. Think of it as a heritage piece reimagined: the same adventurous spirit, updated for today’s wearer who craves both comfort and a touch of nautical cool.
Sebago has never been about shortcuts—every stitch and seam is a nod to true craftsmanship. The Gary Jobson shoe is hand-sewn from full-grain leather, left unlined so it feels light and easy, and finished with a custom sole that literally has Jobson’s name on it. Add in the hand-stitched apron and two-tone laces, and you’ve got a boat shoe that’s equal parts rugged and refined. It’s the kind of footwear that’s ready for deck duty but just as at home at a backyard barbecue. In other words, built to last, built to look good, and built with a wink toward its legendary namesake.
