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Wigwam Mills was founded in 1905 by Herbert Chesebro, Robert Ehany, and Lawerance Bentz in Sheboygan, Wisconsin, a year after the Sheboygan Knitting Company burned to the ground. All three founders were employees of the company and purchased equipment and recruited employees from their former company. The new company was founded under the name 'Hand Knit Hosiery Company.' The company made socks and headwear primarily from wool for the residents and lumbermen of the area. At the time the company was supplied by numerous wool mills in the nearby area.
By 1922, Herbert Chesebro gained partial control of the company after purchasing Bentz's share. The company flourished under Chesebro.
When the stock market crashed, the hosiery industry struggled in the difficult economy of the Great Depression. The company was no exception to this. After Herbert's death, the company struggled under bank loans totaling $100,000. With the help of J.W. Hansen of the Citizens Bank, the company stayed in business.
In 1936, Robert Chesebro, Sr., gained complete control of the company after working at the company for 12 years.
The company devoted up to 75% of its capacity to knitting for the troops overseas. By 1945 the company had expanded its line to include baseball hosiery, anklets, hockey caps, mittens, and socks for all types of activities.
The company prospered for the next 65 years knitting socks, headwear, and other knit products. On January 1, 1957, the company changed its name from Hand-Knit Hosiery to Wigwam Mills based on the popularity of the brand.
The company continued under the leadership of Robert Chesebro, Sr., and eventually the third generation of ownership, Robert Chesebro, Jr.
The 1980s saw growth in many areas for Wigwam. A new logo and more technical synthetic fibers were becoming more specialized. Wigwam developed the Poly-Wool line of performance socks as well as the overnight success—Moraine.
In the 1990s, the company developed the Ultimax and INgenious brands. Each featured a patented sock technology. In 2007, both brands were brought under the Wigwam brand umbrella. Ultimax became Wigwam Pro and INgenious became Wigwam Fusion.