In 1888, Charles Eisenman and Jacob Kastriner pooled their resources to create a company that would provide boys with quality shirts and washtogs. The company was originally named the Kastriner and Eisenmann company but underwent a number of name changes before finally in 1914 settling on Kaynee, a phonetic spelling of the founders' surname initials.

From the very beginning Kaynee offered employees a number of benefits and services that are unheard of in most companies of today’s world. There was a staffed day care free for all employees and workers could visit the children on breaks. In addition to a large cafeteria and kitchen for employees, there was also a recreation room for various indoor games and activities, most notably exercise. A large area was used primarily as a dance floor but could also be transformed into a motion picture theater. The company used this area to host a number of dances and concerts for their employees in efforts to promote company loyalty.

The company also invested in improving the welfare and education of all employees. Medical and dental offices were located on the premises, providing inexpensive and convenient healthcare for employees and their family. Employees could choose to participate in continuation school, the expense taken care of by the Kaynee Company, in order to further their education in avenues related to the business and work they were performing.

In 1915, the company donated a play area to the neighborhood, equipped with tennis courts, a baseball diamond, and sand boxes for younger children. The company looked to improve conditions under which children in the district grew up. This generosity was not altruistic as much as it was a strategic business decision. A company representative stated, “All that Kaynee does is done in the cause of better business. Children who are brought up in the open grow into better men and women, and the better men and women are, the healthier they are- the better employees they will make.”

Kaynee was also able to find a way to promote themselves while simultaneously supporting children’s education and astuteness. From 1940 to 1953, Quiz Kids was a popular weekly show in which a panel of children were asked a series of trivia questions and gave very detailed answers without the help of calculators or notes. Kaynee used the show to promote their line of boys clothing in commercials and started a new Quiz Kids line. Kaynee also sponsored a contest for boys to write in why they wanted to be a quiz kid and the winner would be featured on the show.

Despite the plethora of welfare programs available to employees, problems arose. Workers began pushing for unionization at the behest of the Amalgamated Clothing Workers of America. On November 8, 1934, workers began a strike for unionization. A majority of the employees refused to strike or join the union and was thus susceptible to attacks by strikers. Despite what union leaders claimed, a large number of employees did not walk out; the plant entrances were barred by the picket line and they were unable to begin work. On November 12, Kaynee announced the closing of its Cleveland plants and cancelled all orders placed for delivery. The decision came in the wake of brutal attacks on their employees when riding to and from work and even at their homes. The strike ended January 1935 when the two entities reached an agreement that provided collective bargaining, reinstatement of workers without discrimination, equalization of work, and a reconsideration of wage rates.

The company quickly resumed production and continued operations peacefully until the 1950s. Aetna International bought a large share of stock in 1952 and later sold it to Piedmont Shirt Co. of Greenville, South Carolina. Piedmont bought out the company in 1958 and soon closed both plants (the other being in Williamsburg, Kentucky), putting around 600 employees out of work. The company is still in operation today but is known as the Rifle/Kaynee and is based in New Jersey.