One winter in 1935, Paul Sperry noticed his dog Prince was having a much easier time navigating icy surfaces than he was. After investigating Prince’s paws, he picked out a distinctive zig-zag pattern and cut it into the rubber soles of his shoes; the siped sole boat shoe was born. Since this (slightly dubious) origin story, the modern boat shoe has been an obscure sailor’s footwear, a prep staple and, since the ’80s, a mainstream fashion icon. They’ve come back into vogue recently and are available in hundreds of fabrics and colors, but for the true boat shoe experience you’ve got to look towards Maine. Whether because of their maritime history, manufacturing prowess or just stalwart New England pride, the Mainers do boat shoes right. Here are five of the best that the Pine Tree State has to offer.

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Sperry Made-in-Maine


Because it’s the Classic: The Sperry Made-in-Maine Authentic Original is basically the same shoe that Paul Sperry stitched together in 1935. Needless to say, this isn’t the case of a company being stubborn with a bad design for 75 years. They’re more than three times the price of the normal Authentic Original, which is certainly excessive but not without reason: you get better, thicker leather, vastly improved hardware and American craftsmanship. All of these upgrades paired with classic Sperry DNA make sure that you’ll get your money’s worth.

Eastland Freeport Made In Maine


Because You Need the Best: Horween Leather, a classic silhouette and clam chowder craftsmanship — that works. Eastland combines all the right ingredients to make a shoe that’s hard to argue with. They’re made in a variety of leathers (brown, tan, peanut, navy, navy/green and loden tan, to be exact) and are available immediately (more on that later).

Quoddy Boat Shoes


Because You Can Wait: Just like the Eastlands, Quoddy’s boat shoes are exquisitely handmade. But instead of gaining instant gratification, you’ll have to wait 3-4 weeks as each shoe is made to order. What you’ll get eventually is a more classic three-eyed boat shoe made with your choice of four Horween leathers. That, and the knowledge that you’ve singlehandedly saved American small business.

Ralph Lauren Telford II


Because a Little Color Goes a Long Way: Instead of bringing another brown Maine-made boat shoe into a crowded market, Ralph Lauren decided to liven up a traditional navy colorway with a punchy orange leather lining. Pair with some retina-searing orange chinos and you’ll have the entire Kappa pledge class swooning from your irreverence.

Mark McNairy Suede Boat Shoe


Because Fuck You: They’re suede boat shoes. For those who see themselves sticking firmly to terra firma and don’t mind a healthy hit of irony, McNairy — the cool uncle of #menswear — has you covered. The nonsensical material choice doesn’t mean these shoes aren’t legit: they’re made alongside the rest of Maine’s top-notch boaties. They’ll also last forever and look great, but don’t wear them to the Club, lest Vickers and Muffy “accidentally” stain your $400 shoes with an errant bellini.