Anyways the whole crux of 'timeless' dressing is clothes that don't go out of style every few years, and to do that they have to be attractive yet bland enough to not be on the cutting edge/avant-garde of movements or trends (like retro revival). The whole point is a look that isn't trendy, much less unique to a single person.
Steve Jobs has an iconic look, and that's good because unlike the corporations with faceless ceo's in suits that compete against Apple, people instinctively think of Jobs when they think of Apple. An Apple computer or phone or music player feels as much a product of Steve Jobs attention as the million odd faceless workers behind Apple Inc. and the many contractors and sub-contractors that build them.
His clothes only other purpose besides keeping him warm is to be iconic, and to do that it's got to look different, to stand out, and he has to wear it every time a camera might be pointing at him. It's no surprise most people in a forum dedicated to classic menswear wouldn't approve
In any case after the toll his liver problems have taken on his body, I doubt even the best tailors could make a suit that looked good on him.