Predicting the inevitability of another war, Jacobi and his sons Irving and Paul purchase a surplus of goods from England anticipating not only an embargo on imported goods from the UK, but the scarcity of production.

Irving Press, who began working in the family business shortly after leaving law school in the early 1930s, comes up with the solution of creating odd separates (a sportcoat and trousers) to be worn in lieu of a full suit to offset the shortage of materials.

On the home front, most of the Princeton, Harvard and Yale customers and sales associates are drafted or enlist into the Army in 1940.

The Department of War (now Department of Defense) grants Jacobi and Irving the license to tailor military uniforms. At the time, Yale has the largest officers training school of universities on the East Coast therefore it was not just students at Yale who buy their uniforms at J. Press, but men from all over America who are in Officer training school.

When the war comes to an end, Franklin D. Roosevelt signs the G.I. Bill of Rights into law in 1944 providing benefits to WWII veterans. Among many benefits, the bill provides grants for school and college tuition to top tier universities, diversifying what was once an extremely insular educational system previously available to only the wealthiest and most privileged young men who attended boarding or prep schools. For the first time, Ivy League schools have students who attended public schools from diverse economic classes. This contributes to the democratization of Ivy League style. Particularly at J. Press, a growing need to meet the demands of an influx of new customers where custom clothing may not be an option, our now iconic Ready-to-Wear department is born. It is tailorable, custom-made style at a fraction of the cost and introduces a new wave of men to the world of J. Press.