In the mid-1950s there was [the] development of the Gucci slip-on. There is no question that this now legendary shoe deserves its reputation for having revolutionized casual footwear, which is the reason a Gucci slip-on is included in the costume collection of New York’s Metropolitan Museum.
The Florentine leather firm of Gucci began as a saddlery in the first decade of this century and quickly achieved a considerable reputation for high-quality craftsmanship, detail, and design. The family-owned firm then turned to luggage, handbags, and other small leather accessories, acquiring more cachet along the way, and inevitably began making high-quality and stylish shoes. The famous Gucci slip-on was actually designed, coincidentally enough, in the late 1930s – just about the time “Weejuns” were first being seen on campus. Although the original version was constructed of heavier saddle leather, the design was what it remains faithful to today: a successful effort to retain the comfort of the moccasin while adding the fashion and elegance of a dressy shoe. In short, it was the first shoe that bridged the gap between casual and business wear. This dressy slip-on was refined with fine, lightweight calfskin, a pared-down shape, and a metal snaffle bit, and as such it became avenue-elegant and gained acceptance in corporate board rooms and country clubs alike.
Photo from The Official Preppy Handbook. Was always surprised at this particular endorsement.