The Sebago Portland JIB: A Comfortable, Classy & Timeless Boat Shoe

They’re a favourite at Men’s Health HQ.

This post is sponsored by Sebago | Words by Nadim Nyker |

There is something about a boat shoe that’s timeless. And to know that they were invented in 1935, speaks to its evergreen presence. Fun fact: they were created by American inventor Paul A. Sperry after noticing his dog’s ability to run easily over ice without slipping. Sperry then created the boat shoe; shoes with rubber soles designed to provide grip on a wet boat deck. It goes without saying, they’ve been used by sailors ever since.

Fast forward to the late 1960s and American heritage brand Sebago changed the game, introducing a boating shoe with better craftmanship and durability than other competitors at the time. Sebago then levelled up – launching the Docksides in 1970. Finally, there was a practical and more stylish alternative to the canvas boat shoes of the time, a move that brought major success to the company.

In 2020, we’re still wearing the Sebago Dockside, and they’re a favourite at Men’s Health HQ. Although MH staffers differ in their preferred colour and taste, they’re a quality purchase built to last. My go-to? The Sebago Portland JIB.

Related: This Shoe Literally Gets Better The More You Wear It

According to the brand, the Portland JIB mocs take their name from a specific type of triangular sail. This boat shoe defines a versatile, casual slip-on design that makes it an easy option when you’re looking to trade your sneakers for something as comfortable but different in style.

How To Wear Them

These moccasins in particular, with their brushed suede and multicoloured options, are best played up. Chinos and boat shoes go hand in hand and are a quick, comfortable pick when you need to dress up but still want to have fun.

I wore them to a mate’s engagement party (above) and matched my chinos with a long-sleeved blue cotton shirt; but a plain T or a short-sleeved printed shirt is a great option, too.

Pro tip: Although traditionally boat shoes have been worn without socks, wear them with secret socks for added comfort and to prevent any foot odour.


The Portland JIB brings a sense of class to a shoe that has been around for decades.

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