12. Hugo BossPossibly the most infamous example of a company who collaborated with the Nazis, Hugo Boss designed Nazi SS and Hitler Youth uniforms from 1932 onwards. This contract helped to propel a small-time business into a huge international corporation during the 1930s. Their trademark slick black clothing - which nowadays is designed to have slimming effects - was in fact used in order to command respect from the wider German populace. The majority of these uniforms were also made using forced labour in Prisoner of War and concentration camps. Hugo Boss himself was a member of the Nazi Party and his son, Siegfried, famously commented in 1997: "Of course my father belonged to the Nazi Party. But who didn't back then?" It's probably harsh to tarnish German companies with the same brush as international businesses at the time, but it still doesn't sit correctly that Nazi soldiers during World War II were decked out in Hugo Boss' finest garments, does it?