Founded in 1946 by three New England natives, Sebago stands as a distillation of the Maine way of life. The three founders, all close friends, instinctively transferred their love of the outdoors and marine roots into the Sebago image and product. This, by nature, meant that Sebago products became known for their superior construction, refinement, and unwavering attention to details — three qualities that live on to this day.

In 2017, Sebago moved its production back to the Dominican Republic and Mexico where it began. As a result, the brand’s output also shifted, becoming closer and closer to its original, 1960s form. Footwear shapes and apparel silhouettes returned to their high-standard materials with a focus on durability and elegance, rounded out with genuine hand stitching.

This return to previous glory meant a return to serious prep. During the 1960s, Sebago was a key brand for preppy style and Ivy leaguers — so much so that it was even mentioned in Harvard’s own style guide. Handmade quality and premium materials meant that Sebago stood not only as a style icon but also a status symbol.

Prep’s having a moment, plain and simple. It’s a new chapter for loafers, but certainly not the first. From the mod-populated streets of London to the cobbled streets of Milan, loafers have been (and still are) a menswear staple that crosses cultures, borders, and generations. What’s more, with the world of sneakers hitting something like terminal velocity, there’s a sense that loafers — the shoe of choice for any prep master — are a logical next step for the generation who grew up on sneakers.

And as our tastes lean towards the allure of loafers, Sebago is enticing us ever closer with a new, contemporary focus as we reach the brand's 75th anniversary. Working in tandem with labels like Engineered Garments, Universal Works, Alanui, and many more, Sebago has extended its enduring appeal to a new demographic. That said, classic Sebago loafers accompany Sebago's prep-centric apparel and remain at the forefront of the label’s output.

It's not all loafers though. In keeping with the brand's prep focus, the footwear selection is split into three areas: Citysides, Docksides, and Campsides. These sections do what they say on the tin. Citysides caters to city styles like clean loafers while Docksides is where you'll find Sebago's fan-favorite boat shoes. As for Campsides, this category finds its home in the outside world, taking inspiration from the wild beauty of the National Parks across the US. In our selection, we've touched upon all three areas to prove that Sebago has all sides covered, and it's the only place to begin your new era in footwear.

Scroll down for six of our favorite pairs of Sebago shoes right now.

Classic Joe

Classic Joe Loafers

Classic Joe Loafers

$198

Sebago

Buy at Sebago

Where better to begin our Sebago shopping than with Joe? This pair lives up to the archetype of the classic leather horsebit loafer. A slim silhouette features minimal detailing, placing the focus solely on the smooth, corrected grain leather construction while an aged, gold-tone horsebit runs across the vamp.

Classic Dan

Dan Loafers

Dan Loafers

$198

Sebago

Buy at Sebago

If you're on the hunt for pure, unadulterated prep with no distractions then Sebago's Dan Loafers are the one for you. This classic penny loafer features smooth corrected grain leather to stand the test of time and is hand-sewn with the finest craftsmanship. This pair is an homage to the passion of the Sebago founders.

Classic Dan Woman

Dan Loafers

Dan Loafers

$188

Sebago

Buy at Sebago

Add a touch of variation to your fits with this pair of two-tone Dan Loafers. White and black clash in the leather upper for a bold, eye-catching take on Sebago's classic Dan Loafers.

Docksides Portland

Portland

Portland

$156

Sebago

Buy at Sebago

While Sebago’s footwear offering is typified by its loafers, there’s a whole host of other prep classics in there too. Somewhere in between a loafer and a shoe is the boat shoe. This leather pair features a classic 360-degree lacing system and is made of unlined full-grain leather.

Portland Flesh Out

Portland Flesh Out

Portland Flesh Out

$156

Sebago

Buy at Sebago

The Portland moc bears in its very DNA an innate affection and bond towards the city of Portland, one of the largest seaports in New England, also host of a world-famous Yachting Club. This suede pair puts style first.

Cayuga

Cayuga

Cayuga

$250

Sebago

Buy at Sebago

A 3-colored, hand-sewn upper combines with rawhide laces and a lightweight EVA die-cut sole for a classic shoe with modern comfort. The Cayuga Mocs are the perfect outdoors shoe to wear around camp, or for a stroll around town.

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