[demallien]

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.