This is important yet overlooked! There is a lot of advice for up and coming founders on HN (and other places) ranging from scalability minutiae to naming your company, which are all important of course, but there is very little advice on how to dress to create a personal signature style.
Why hasn't a site that aims to do this hackers/startup founders crop up, with advice like, what sort of sweater would look good with your Timbuk2 bag, etc.
The idea of imposing a standard uniform or wearing the same thing everyday can be viewed as a form of imposing conformity over individuality (mostly the uniform thing, and less the personal style thing).
That said, for a US company (especially at that time), such thinking was definitely 'outside the box,' so it could also be viewed as being consistent with the 'Think Different' slogan.
The idea of wearing the same thing everyday is hardly 'outside the box'. Baseball players, judges, police officers, firemen, hospital staff, waitresses, painters, plumbers, construction workers...I'll stop now.
In Jobs's case, I think it had more to do with efficiency. I believe Einstein also wore the same outfit every day, saying each person had a finite amount of time for thought, and he didn't want to waste it picking out clothes.
'Think different' and individuality are not really synonymous. A group of people can 'think different' by imposing conformity within their team and working as a unit.
This is important yet overlooked! There is a lot of advice for up and coming founders on HN (and other places) ranging from scalability minutiae to naming your company, which are all important of course, but there is very little advice on how to dress to create a personal signature style.
Why hasn't a site that aims to do this hackers/startup founders crop up, with advice like, what sort of sweater would look good with your Timbuk2 bag, etc.