The Rancourt & Co. Boat Shoe
Credit: Photograph by Michael Pirrocco

When it comes to American dress shoes, the boat shoe is as classic as it gets. The style popularized by Connecticut shoemaker Paul Sperry in the thirties is Rancourt's most admired product because it showcases the company's specialty: handsewn Moccasin construction. The Rancourt's take on the iconic shoe relies on Chromexcel leather sourced from Chicago's Horween Leather Company – itself a family-owned business – and cut with steel blades before being pulled together with waxed thread for a precise fit. The shoes are made in much the same way as penny loafers, which were Dave Rancourt's specialty when he was making private label collections in the sixties. The Rancourts remain the best in the business at "Moc Toe" construction and their boat shoes are as durable as they are handsome. [From $227;]