A Penny for Your Loafers

One of the must-have items of the season is, apparently, the good ol penny loafer. Penny loafers were named as such because they could be decorated with a penny (or often, a dime). I didn’t realize there was actually an urban legend behind this:

In 1934 John R. Bass (a bootmaker in Wilton, Maine) started making loafers and called them Weejuns. These had a strap across the upper part of the vamp that was shaped like a pair of lips. The mouth opening soon was used to hold an ornament (such as a penny), and thus penny loafers became a style. Penny loafers often held a dime instead of a penny. (From Wikipedia).

In the days of yore, the penny loafer was a low-heeled shoe through and through, with a strong masculine vibe. These days the penny loafer, just like the oxford, has gone through a high-fashion transformation.