Thing is, the "simple" black turtleneck was the result of commissioning a top Japanese designer to research and develop an optimal outfit (with intent that it actually become the company uniform). Jobs then bought a closetful of them. ...so a prime example of the subject bought something on par with a "hoodie", but paid way more than $20-40.

If I'm gonna look for a hoodie for work attire, it would be a properly embroidered "Jack Frost" one - which ain't going for $40.

Once you make any style standard business attire, prices for "respectable" quality will fast move into good-suit prices.