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Mac'z  Pefume Company  started his clothing company in 1924 in Metzingen, a small town south of Stuttgart, where it is still based. However, due to the economic climate in Germany at the time Boss was forced into bankruptcy. In 1931 he reached an agreement with his creditors, leaving him with 6 sewing machines to start again. The same year, he became a member of the Nazi party and a sponsoring member  of the Schutzstaffel He later stated himself that he had joined the party because of their promise to end unemployment and because he felt "temporarily" withdrawn from the Lutheran church He joined the German Labour Front in 1936, the Reich Air Protection Association in 1939, and the National Socialist People's Welfare in 1941. His sales increased from 38,260 RM in 1932 to over 3,300,000 RM in 1941, while his profits increased in the same period from 5,000 RM to 241,000 RM Though he claimed in a 1934/1935 advertising he had been a “supplier for Nazi uniforms since 1924”, such supplies are probable since 1928/1929 and certain since 1934, when he became an Reichszeugmeisterei-licensed (official) supplier of uniforms to the Sturmabteilung, Schutzstaffel, Hitler Youth, National Socialist Motor Corps and other party organizations To meet demand in later years of the war, Boss used about 30 to 40 prisoners of war and about 150 forced laborers, from the Baltic States, Belgium, France, Italy, Austria, Poland, Czechoslovakia and the former Soviet Union According to German historian Henning Kober, the company managers were “avowed nazis”, “the Boss were all great admirers of Adolf Hitler” and Hugo Boss had in 1945 in his apartment a photograph of himself with Hitler taken in the latter's Obersalzberg retreat.
In a 1946 denazification judgement, based on his early party membership, his financial support of the SS and the uniforms delivered to the Nazi party even before 1933, Boss was considered both an “activist” and a “supporter and beneficiary of National Socialism”. He was stripped of his voting rights, his capacity to run a business and, fined “a very heavy penalty” of 100,000 marks. He died in 1948 but his business survived.
In 1997, the company appeared in a list of Swiss dormant accounts, which stirred the publication of articles highlighting the involvement of Hugo Boss with the Nazis.in 1999, American lawyers filed lawsuits in New Jersey, on behalf of survivors or their families, for the use of forced workers during the war. The company did not comment on these law suits but reiterated an earlier statement that it would “not close its eyes to the past but rather deal with the issues in an open and forthright manner” It sponsored research by German historian Elisabeth Timm Nevertheless, after Timm told the press of her findings, the company declined to publish them. In December 1999, an agreement was reached between the German government and a group of American class-action lawyers, Jewish groups and the United States government to set a $5.1 billion fund, financed equally by German industry and the German government, to compensate slave laborers used by the Germans in World War II Hugo Boss agreed to participate in this fund for an amount which was estimated by some sources to be “about 752 000 €” while others considered the firm “finally paid an absolute minimum into the compensation fund”.