Hugo Ferdinand Boss was born on July 8, 1885, the fifth and youngest child of Heinrich Boss and his wife Luise, who jointly owned a lingerie and linen shop in the Swabian town of Metzingen.

Hugo F. Boss opened his clothing factory in 1924 with financial support from two other manufacturers in Metzingen. It made all kinds of garments by hand - from shirts to traditional southern German loden jackets. One of the company's first major commissions was for a large batch of shirts for the Munich-based textiles distributor Rudolf Born, which also included brown shirts for the National Socialist Party. While most likely unaware of the shirts' intended purpose, Hugo F. Boss advertised his company during the mid-1930s as a "supplier of Party equipment since 1924."

Hugo F. Boss became a member of the National Socialist Party in 1931, which then placed orders with him for uniforms. Later, at his hearing during the postwar denazification process, Hugo F. Boss declared that he had joined the National Socialist Party because it had promised to do something about the rampant unemployment afflicting the country. Subsequently he expanded on this point by stating that he would never have received the orders that rescued his company had he not been a member. While this may have been true, one must not interpret Hugo. F. Boss' comments as suggesting he was hostile to the Nazi Party.