Uh... there are plenty of techies who wear the same clothes every day (sometimes literally), who do it because it feels right for them, and who aren't concerned about fashion or trends. Jobs is hardly unique in the 'I don't care' fashion stakes among techies. Period.
Jobs wasn't unconcerned with fashion. If he was, then he would wear any damn thing that was in his closet.
He made a dedicated effort to create a fashion "brand" to the point that people know what kind of sneakers he wore.
Jobs might not have been a great engineer or techie, but he was a great visionary, designer, and marketer. He created (and recreated) one of the greatest brands in America. I don't doubt he applied the same principles to his wardrobe as he did to his company.
Exactly. It is a mistake to think that Jobs had not thought carefully about the clothes he wore - it's just that his approach to clothing was the same as his approach to technology - he seems to have believed that there was an optimal set of clothes for him, and that any deviation would simply mean that he wasn't wearing the best clothes for his purposes. Much like the discussions raging over the fact that the iPhone screen size hasn't varied at all - one size has been deemed optimal, and deviations from that size mean that the product must by definition be suboptimal.
