Watch When is Boss's Day 2025? How celebration began, gift ideas National Boss Day is celebrated on Oct. 16 each year. It started in 1958 when a State Farm employee registered the holiday with the U.S. Chamber of Commerce. Employees are recognized several times throughout the year with celebrations like National Employee Appreciation Day in March and Labor Day in September, and luckily for employers and bosses, there is a designated day for them too. National Boss's Day is celebrated in mid-Octo