The style was popular in Europe and North America in the early 20th centuries among both boys and adult men. As the name suggests, it was at the time associated with newspaper boys. This gives rise to a misunderstanding. It is true that many newspaper boys and other working boys at the time wore flat caps along with other styles. This style was not, however, worn only by boys.

Flat caps were very common for North American and European men and boys of all classes during the early 20th century and were almost universal during the 1910s-20s, particularly among the working 'lower' classes. A great many photographs of the period show these caps worn not only by newsboys, but by dockworkers, high steel workers, shipwrights, costermongers, farmers, beggars, bandits, artisans, and tradesmen of many types. This is also well attested in novels and films of this period and just after. Eight-piece style caps are essentially an offshoot of a scottish tam o' shanter.

While they were worn by boys and men of all social classes, they were worn by the 'upper' classes primarily for leisure activities, and the style became associated with well-to-do country sportsmen, drivers and wealthy golfers.