From the beginning of history men wore skirts (long like robes and short like Scottish kilts). Then, in the late 14th to early 16th centuries breeches were popular. These were pre-cursors to the evolution of shorts.
Breeches were knee length tight pants worn with hose.
Knickerbockers were loose breeches gathered or pleated into a buckled band at the knee. They were the fashion for boys around 1863 and worn with a short collarless jacket.
In the 1890’s, men started wearing knickerbockers for golf and sportswear. Knicker boxers were also called or plus fours, because they came 4 inches below the knee.
Older boys wore a vest (waistcoat) and after 1890’s a Norfolk jacket with their knickerbockers. Knickers, actually refer to ladies underpants, but is a common short word for knickerbockers.
Knee pants were short light pants extending to the knees. They were worn by boys 8 to 16 years old from the late 19th century until after WWI.
The word “shorts”, an abbreviated version of the word “short pants” came into being in 1920’s. This was at the time when younger boys ages 2 to 8 began to wear a wider leg style.
Shorts in the 1920s-1930s
During the 1920’s men wore one-piece swimsuits, which covered their chest.
By 1932 the European craze of for swimming without shirts at private beaches gained momentum. New elastic fabrics started to be used in swimwear in the 1950’s, promising a better fit. These elastic fabrics held its shape even after the fabric was wet.
In the 1930’s shorts were popular with adults for camping.
Senorita de Alvares played tennis in a below the knee divided skirt in 1931. This set the stage for Alice Marble to wear shorts in 1933 for a professional tennis match. That event helped the acceptance of shorts in sporting events.
The first sight of tennis shorts in public was on a man, Bunny Austin. He wore shorts at the 1932 U.S. Men’s Championships at Forest Hills, New York.
Bermuda shorts were created at the beginning of the 20th century by British military forces, not in Bermuda, in London!
The British military wanted their personnel appropriately, but lightly attired for duty in tropical parts of the Empire!
Before the “standard issue”, troops were already cutting off their trousers at the knees to get some heat relief. There were British Regiments in Bermuda where civilians started copying the military shorts.
Men had accepted Bermuda shorts for leisurewear by 1950. They were often seen paired with sport coats in men’s fashion magazines, even neckties and, of course, long socks.