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Sperry Top-Sider 75th Anniversary Collection

Celebrate three-quarters of a century of a nautical clothing icon with the Sperry Top-Sider 75th Anniversary Collection ($55-$88). Created in 1935 by sailor Paul Sperry, who created the sneakers' unique Razor-Siping bottom grooves after watching his dog run across a frozen pond, these laid back kicks are nearly synonymous with boating, and are available in three styles, all arriving in limited edition replicas of the shoes' original packaging.

  • Tretorn Klipporone Boot

    If you're on the job or simply looking to add some outdoorsman chic to your wardrobe, take a gander at the Tretorn Klipporone Boot ($145). This high-top boot features nine eye laces, a combination smooth and textured leather upper, textured, grooved rubber sole, two-tone laces, and a reinforced rubber midsole and toe cap. While they might look good at a country cookout or impromptu fishing session, don't expect to roll around midtown without drawing some strange looks.

  • Clarks Originals Wallabee

    Add some simple style to your winter wardrobe with Clarks Originals Wallabee ($130). Based on Lance Clark's original comfort shoe from 1965, the Wallabee is a hand-sewn moccasin featuring a suede upper in one of three shades, plantation sole construction, and a mid-height cut. Their simplicity isn't likely to wear well with dressier attire, but they should go great with plenty of other garb, from jeans to pajamas.