Workwear isn't "frowned upon", it's just not the ne plus ultra of aesthetic choice right now. There's lots of people who still dress very workwear-esque - and even someone like mellow incorporates a lot of workwear elements into his look.
Having a "uniform" isn't about being able to dress quickly and easily, because, let's be honest, getting dressed isn't hard. It's much more about being content with the clothes you own and wearing the same few outfits every day, and that's a lot harder than simply owning a small number of pieces that go together and fit well.
Clothing is a form of expression, and while the act of wearing a simplistic, repetitive uniform sends a message in and of itself, it's much easier to be happy with how you're expressing yourself if you have lots of options.
What I find annoying about someone like reedo is that he doesn't even know what he likes because he's incapable of standing still for more than a minute and simply wearing the pieces he has. I sell and buy a lot of clothes, but I have a core wardrobe that, while evolving aesthetically, has remained very consistent over the last few years, and has allowed my style to slowly develop into something I'm happy with.
For too many people clothing is all about hype and group acceptance in the context of styleforum. Where's the originality? And by originality I don't mean owning lots of rare brands, I mean actually wearing your clothes and owning your style. That's the difference between mikey and reedo: one is slowly expanding his wardrobe (the good approach), while the other is caught up in this endless hyped kop cycle, always hoping that the next purchase will finally be the one that makes him happy with his wardrobe, chasing a nirvana that is always elusive.
Dressing well, and having a nice wardrobe, isn't about having that one amazing item that ties everything together. It's more than the sum of it's parts, and that's why there's a reason that among two people wearing an identical outfit, one looks comfortable and one looks like a fashion victim.