1940:
To protect and promote the Jockey® brand name, Cooper's commissioned well known sculptor and painter, Frank Hoffman, to produce the Jockey Boy image that symbolized pride in the brand. This original bronze figure was just short of one foot in height, and it was reproduced to precise dimensions in the point-of-purchase figure. It served as the company's trademark for five decades.

1942:
Cooper's contracted with Swiss licensee, Vollmoeller Knitting Works, located in Uster, just north of Zurich. Even before WWII, Swiss men developed an affinity for Jockey® shorts. When wartime trade blockades ended the importation of luxury items like American underwear, the demand went unfilled. That is when Hans Vollmoeller negotiated the licensing agreement with management in Kenosha, the details of which were settled by mail and Teletype.

1945:
During WWII, Jockey contributed to the military effort, making parachutes and keeping men on the war front, as well as the home front, comfortable in a full range of Jockey® styles.

1946:
Jockey was a champion on its way to becoming a legend. No claim was too great, including an endorsement from baseball's home run king, Babe Ruth. Athlete endorsements would remain an important merchandising tool for the company in years to come.

1947:
The Jockey® brand name was stitched into the waistband of the underwear for this first time. Jockey highlighted this industry first with ads stating, "Look for the Brand on the Band" - two famous trademarks - "Jockey®" and "Y-Front®."

1948:
In a search for a new mill to make woven boxer shorts, Cooper's worked with Giffin Manufacturing, in the town of Carlisle Kentucky. Cooper's became one of Giffin's first customers. Harry Wolf liked the quality of Giffin and soon made a minority investment in Giffin to ensure long-term Cooper's production at the plant.