Did he just take from the people and give to the enlisted until he was able to take what he needed from the countries he invaded?
A couple of remarks:
At that time, Hugo Boss was not a premium brand. His company manufactured work clothes and later various uniforms. Note that the uniforms were not designed by him, he was merely a manufacturer.
Volkswagen cars were supposed be be purchased with a savings plan, i. e. the customers basically had to pay in advance. As it happened, WWII broke out before the first cars could actually be delivered.
Source: Standard Catalog of Volkswagen, 1946-2005
First of all, it was the SS uniforms that were produced by Hugo Boss, not desigend by him. Back then the SS was a very small formation and strictly not even a military unit (they were a guard/watch unit) and Hugo Boss was certainly not a prime brand.
Volkswagen cars were deigned to be extremely simple and cheap to produce. It was touted in propaganda that each family could own one if they saved 5 marks a week. Of course, there were only a few produced before the funds saved were converted to war bonds and the money used for the war effort.
German enlisted men did not have substantially higher pay than other enlisted men in other armies. However, the nazis had set the exchange rate of the mark so high, no-one outside Germany (or by force, occupied territories) accepted it. German soldiers could buy a lot with their pay in occupied countries because of this. In essence, it was a formalised way of plunder for the soldiers.