The Story behind the
Regatta Shoes
Boat shoes, as the story goes, were invented in New Haven, Connecticut in 1935. Paul A. Sperry (as in Sperry Top-Sider) was an avid and accomplished sailor but struggled, as everyone did, with maintaining a grip on his ship deck. One winter day, while noticing his dog walking across the ice with no slippage to speak of, the idea came to him to create a shoe with a sole made of rubber with little herringbone shaped grooves carved into the bottom called siping. This gave the shoe a much better grip on wet ship decks and so was born the Sperry Top-Sider. The comfortable shoe quickly became a staple of the American Eastern Establishment on the Eastern Seaboard.
As the Ivy League students of the time began using them not only on sailboats, but on campus and in town with cotton chinos and grey gabardines, the style spread across the country. By the 1960s and 70s it became a staple of many the preppy man’s wardrobe - described as an essential part of the preppy wardrobe in The Official Preppy Handbook (1980) by Lisa Birnbach. Since the 80s the style spread even more. In the early 2000s it wouldn’t have been uncommon to see a man in landlocked cities sporting a boat shoe in summer months anywhere in the western world (and maybe Japan). As all the classic styles that sprung from the mid-century American Ivy League, the style never died out.
Our Boat Shoe comes in a moccasin construction which gives the shoe the iconic ruffles in the leather. Made in Portugal using high grade leather, the suede leather is from M2 tannery, and the deer skin is unlined, using leather from M2 tannery as well.
The shoes fit well with a pair of linen shorts, cotton trousers or even a linen suit to add a casual feel to a tailored outfit. Explore the different looks below.
Formal Outfit with Cavour Deer Skin Boat Shoes
Semi Formal Outfit with Cavour Suede Boat Shoes
Casual Outfit with Cavour Suede Boat Shoes
