Grace Kelly is preppy and casual in cuffed pants and loafers.
I'm looking for a pair of loafers -- they are classic, versatile and preppy. My first thoughts for inspiration were Grace Kelly in High Society or Audrey Hepburn in Funny Face, but other major icons of the day were seen sporting them, from Brigitte Bardot to James Dean and Paul Newman.
The shoe's origins were rather unlikely:
The penny loafer originated in the 1930s when loafers of several varieties were fashionable as men’s and women’s shoes. Somewhat unbelievably, this fashion started with the Spaulding company when they produced shoes styled after those of Norwegian dairy farmers that had appeared in an article in Esquire Magazine. (Source)
The "penny" in its name comes from John Bass's idea to add a little embellishment to the loafer, or a decorative touch, often held in place by a small object, like a penny.
Here are a few styles I've been lusting after:
1, 2, 3, 4, 5, 6