This is cargo cultism. Aping dress habits isn't going to imbue you with the attributes that led to success for Jobs.
The lesson a would-be successful person should learn from Jobs is to focus on what's essential. If you become so distracted with trying to copy minor habits, you've missed the point. And Steve Jobs was successful far before he started wearing the same thing all the time, anyway.
That wasn't the reason given though. He didn't say he did it just because Steve Jobs did it. He said that he did it for the same reason that Steve Jobs did it...which is that he doesn't have to think about what to wear.
- I call that BS. That is your small thinking and so you should limit yourself to it. I say go emulate successful people and do what you want to do.