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.

Oh wait....bums.

It's 'outside the box' for office workers.

And let's not forget 80% of Apple employees.

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.

Einstein only wore identical suits to occasions requiring suits. For the rest of it, he was laid back.

Maybe Jobs will also be included in this account of famous people with Asperger's syndrome.

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC539373/

'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.