Founded in 1946, Sebago has outfitted everyone from sailors to Kate Middleton in its hand-sewn, moccasin slip-on shoes. Though based in Rockford, Michigan, Sebago’s timeless aesthetic is New England-inspired through and through — a reflection of the origins of company founders Daniel J. Wellehan, Sr., Joseph Cordeau, and William Beaudoin. Since starting out with a basic penny loafer design, Sebago has expanded its collection over the decades to include men’s and women’s high-top sneakers, ankle boots, boat shoes, chukkas, and many other styles. Sebago’s collaborations with the likes of NYC shoe-designing wunderkind Ronnie Fieg have kept the label fresh and innovative. We like the cut of your jib, Sebago.