Fidelity Sportswear was established in 1941 in Boston, Massachusetts as a military supplier to the US Navy. Gerald & Stewart Webber, the present day owners of Fidelity Sportswear, have been involved with the company since their youth. Their father, Edward Webber, was an original partner in the American outerwear company and worked with his sons in the factory in their teenage years. The brothers have maintained a hands-on approach to the family business and remain active in all areas of the company. To this day, all manufacturing takes place in Boston under one roof with the hands-on supervision of brothers, Gerald & Stewart Webber.

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