I worked at Apple for 5 years. Some of the best engineers I know would routinely show up to work in pajamas. There are just as many, if not more, "poorly-dressed" people working there as at any other tech company.
The casual clothing trend, at least in Silicon Valley, has roots in 60's-70's counterculture. The idea that you need to wear a suit in order to do your job, or to dress like an IBM drone, was explicitly rejected, along with a whole slew of other ideas which were perceived as needing reexamination. Apple was one of the companies which best represented that counterculture influence and its success in shaking up entire industries. To tie them to some notion of stylish dress equaling success is ludicrous.
The casual clothing trend, at least in Silicon Valley, has roots in 60's-70's counterculture. The idea that you need to wear a suit in order to do your job, or to dress like an IBM drone, was explicitly rejected, along with a whole slew of other ideas which were perceived as needing reexamination. Apple was one of the companies which best represented that counterculture influence and its success in shaking up entire industries. To tie them to some notion of stylish dress equaling success is ludicrous.