Sebago Revives a Nautical Icon: The Portland ‘Gary Jobson’ Docksides

Sebago has dipped back into its maritime archives to relaunch one of its most recognisable icons — the Portland ‘Gary Jobson’ Docksides. First introduced in the 1980s and named after the American yachtsman and America’s Cup winner Gary Jobson, the shoe returns for Autumn/Winter 2025 with a sharper focus on craftsmanship, performance and quiet luxury.

The collaboration between Sebago and Jobson isn’t new — it’s a partnership that dates back to 1977, when the brand first dedicated an exclusive line to the sailor. The Portland quickly became a cult favourite, admired as much for its timeless design as for its functionality on deck. Jobson himself once described it as “the most technically advanced boat shoe ever made” — high praise from a man whose life has revolved around precision and performance.

For the relaunch, Sebago has gone back to the DNA of the original, refining rather than reinventing. The Portland Gary Jobson is offered in three iterations: two cut from supple suede for a softer, more refined feel, and one crafted from full-grain leather for those who prefer the look and durability of the original deck shoe. Each pair is hand-stitched and built on Sebago’s classic non-slip rubber sole, updated with a new tread pattern featuring Jobson’s signature. It’s an understated detail, but one that cements the collaboration’s authenticity.

While the Docksides will always be synonymous with life at sea, the new Portland has been reimagined with versatility in mind — the kind of shoe that works just as well on a marina deck as it does on a city pavement. In true Sebago fashion, it balances form and function: traditional craftsmanship, premium materials and a design language that never tries too hard.

This isn’t a nostalgic reissue, but rather a modern take on a classic — proof that the best designs don’t need to be reinvented, only refined. For men who appreciate the craftsmanship of a shoe that tells a story — from yacht races to weekend wear — the Portland Gary Jobson is a worthy addition to the modern wardrobe.

The Sebago Portland ‘Gary Jobson’ Docksides are available now in select retailers and online at sebago.com.