The beanie cap is typically made of wool felt, and was popular amongst school age boys from the 1920s to the early 1940s. Beanies are brimless and either have a small embellished visor or, more commonly, no visor at all.
One popular style of the beanie during the early half of the twentieth century was a skullcap made of four or six felt panels sewn together to form the cap. The panels were often composed of two or more different colors to make them novel. This type of beanie was also very popular with college fraternities as they would often incorporate school colors into the beanie.
Another style of beanie was a formed and pressed wool hat with a flipped up brim that formed a band around the bottom of the cap. The band would often have a decorative repeating zig-zag or scalloped pattern cut around the edge. It was also quite common for schoolboys to adorn their beanies with buttons and pins.
By the mid 1940s, beanies fell out of popularity as a hat in favor of cotton visored caps like the baseball cap although in the 1950s and possibly beyond, they were worn by college freshmen and various fraternities as a form of mild hazing.
In the early 1990s, the beanie saw a reemergence in popularity due to the "grunge" clothing trend as well as the popularization of snowboarding and other cold weather sports activities. The modern beanie is usually made of fleece, or special synthetic material that wicks moisture away. Woven versions, resembling tobogganing caps, are also popular sportswear accessories for winter sports -- such as snowboarding.
As one travels north into colder climates the beanie swings away from the 'form' it favors in the south to the 'function' of the north. In areas such as Canada and the northern states it is more functional and the popular name changes to tuque.
In a Calvin and Hobbes comic strip, Calvin eats several boxes of cereal to get the required proofs of purchase to mail off for a propeller beanie. After waiting six weeks for delivery, he is ultimately disappointed, as he expected that the cap would allow him to fly.
The film Meet John Doe prominently features a character named Beanie who is always seen wearing a hat; it is not clear whether or not his hat qualifies as a beanie, or if this is the source of his name.
In the Southern American English, the beanie is also referred to as a toboggan.
More detailed information on beanies including some information on the propeller beanie is available on Historical Boys' Clothing
The second is a close-fitting knit or crocheted cap which is usually made of acrylic or wool, synthetic material, man-made or fleece. They can be worn by either sex, but historically have been more commonly worn by men. These hats protect the head and ears from cold and wind chill, or are worn as a fashion item, often heavily branded with the name of the designer, sporting team insignia or colors, or with other logos or slogans. This type of hat is also referred to as a snookie.
In Canada, where such hats are almost ubiquitous, they are called a tuque (or a toque: there is debate on the proper spelling). The term beanie is used mainly in New Zealand, Australia and the United Kingdom. Some English-speakers, especially military, refer to beanies as watch caps. In the United States, this kind of headgear is variously known as a beanie, knit hat, knit cap, sock cap, stocking cap, toboggan, boggan, skull cap, skully, warm winter hat, ski capor, chook, or ski cap depending on the region. Among the Amish, it is sometimes referred to as a sipple cap. It is worn low on the head, covering the forehead, and can be pulled down over the ears as well, though normal usage keeps a turned-up cuff. There are two main varieties of beanies, those that hug the top of the head, and those that leave the top couple of inches of the hat unstretched on top of the head. In India it is usually called a monkey cap.
They are also called woolen or wooly hats, or bobble hats if they are topped with a pompom, which is common. A variation of this type of hat, which is pulled down and worn over the face, with appropriate holes for the eyes and mouth is called a balaclava (or a ski mask in the U.S.). A visor beanie is a relatively new variety which foregoes the cuff for a cardboard-spined brim.
Beanies were popular among schoolchildren in the early to mid-20th century. Some hat historians believe schoolchildren began wearing beanies in imitation of their working-class fathers. Ray Nelson made a whimsical addition to these caps with a plastic propeller attached to the crown. The propeller beanie increased in popular use through comics, and eventually made its way onto the character of Beany Boy of "Beany and Cecil."
It is probably due to this infantile connotation that some universities began introducing the freshman beanie around 1920. These were simple beanies, either with or without a brim, usually with an insignia of the institution and often with the class year, and usually made of wool. It was usually required that students wear these beanies at all times when they were on campus for the entire freshman year. At some institutions there was often a contest in the fall, such as an athletic competition between the freshman and sophomore classes, the winning of which would relieve that year's freshman class from having to wear the stigmatizing beanie. With the social changes of the 1960’s, these traditions were abandoned, often by the simple refusal of whole classes to wear the beanie.
Today, computer geeks and other technically proficient people are sometimes pejoratively referred to as propeller heads thanks to the one-time popularity of the propeller beanie. Professional Speaker Rich DiGirolamo wears his beanie everywhere to shift the thinking of his audiences and remind them to poke fun at and embrace organizational change.