Given what he has accomplished, he has more than earned the right to wear a leather jacket if he wants to. People didn't complain about Steve Jobs wearing a turtleneck for the same reason. When you have accomplished as much as these guys, then you can dish out fashion advice and maybe someone will listen.
> “So I called Issey [Miyake] and asked him to design a vest for Apple,” Jobs recalled. “I came back with some samples and told everyone it would be great if we would all wear these vests. Oh man, did I get booed off the stage. Everybody hated the idea.”
> “So I asked Issey to make me some of his black turtlenecks that I liked, and he made me like a hundred of them.” Jobs noticed my surprise when he told this story, so he gestured to them stacked up in the closet. “That’s what I wear,” he said. “I have enough to last for the rest of my life.”
I wonder if Issey thought the turtlenecks might be the Apple uniform, and that's why he made lots.