From a local estate sale, two vintage Indianapolis Motor Speedway / Indianapolis 500 drivers caps. Both are white cloth, lined, one size with velcr closure, machine stitched, with some soiling especially along sweat band inside. One looks like it has make-up soiling it.
Based on the designs, these 2 Indianapolis 500 racing caps likely date back to the
late 1980s or 1990s.One AI site suggested the 1970s.
Reasoning:
Left Cap: The left cap features a classic checkered flag with "INDIANAPOLIS 500" underneath. This style was very popular in the late 80s and 90s, as seen in various vintage Indy 500 merchandise from that era. Tag has been cut out
Right Cap: The right cap displays the iconic Indianapolis Motor Speedway (IMS) "Wing and Wheel" logo with flags, a design that was prevalent on IMS merchandise during the same period, especially in the 1990s. Several search results specifically mention IMS caps from the 90s featuring similar embroidered logos. Has tag saying Made in USA.
These caps have a snap, reminding me of chauffeur's caps but can also be called drivers caps or racing caps due to their historical connection with motor racing and the Indy 500. White background.