Cigar Aficionado

Allen-Edmonds Eastport Boat Shoe

Standard evolution in menswear is a trickle-up progression. Garments made for utility—riding, hunting, fishing, warring—gain cache among the leisure class and become fashion items built for looks, not function. Rarely do they morph into something that both works and looks better, as Allen-Edmonds' new Eastport boat shoe has.

Gentlemen of a certain age will recall the leather, rubber-soled, sure-footed moccasin as the work shoe of choice for those who slathered varnish on rub rails and fo'c'sle hatches, applied copper paint on hull bottoms, and crewed yachts. Ship chandleries stocked boat shoes next to marlinspikes, fids and nautical charts. Then the yachting crowd discovered them and made them standard preppy cobblery—worn miles from any winches or mainsails. And the boat shoes began to appear as wild-hued offshore (no pun intended) knockoffs, any nod to boating unintentional.

Happily, old-line American shoe manufacturer Allen-Edmonds has reconsidered the genre and created a boat shoe firmly anchored in sailing heritage. Word has it that the chairman is an avid yachtsman.

Purists will immediately notice the details that make a boat shoe great: the siping (tiny razor cuts in the sole that grip even wet decks with a flex of the foot); the true moccasin (a one-piece leather vamp sewn by hand with two needles and waxed thread); the familiar leather upper (more durable in water than canvas because it breathes, and it resists salt).

But tradition has also been tweaked toward comfort. Inside is a full leather sock liner and latex "memory" foam that rebounds and resists flattening. The Eastport's blucher sports three pairs of eyelets, not two, that make for a surer fit.

No manufacturer introduces a sport shoe without high-profile professionals to show them off. Allen-Edmonds sponsors a racing yacht with its crew outfitted in Eastports. While the shoe will surely end up on the feet of landlubbers, we suspect the Eastport is destined to feel most at home doused with salt spray.