The way people dress, in my opinion, shouldn't be a huge factor in basing judgment on them. It definitely shouldn't define their worth.
I am all over the place in the closet...I have flannels, dresses, blouses, graphic tees and random junk I think might look somewhat alright.
Sometimes, I'm dressed very prudishly, and I look like a "librarian," as I've been told. While other times, I'm a slovenly mess or hardly covered.
Sometimes, I pair things that probably shouldn't be paired.
Maybe it's because I try to refrain from snobby thoughts, and I'm human so my appearance isn't 100 percent elegant (honestly, wouldn't want it to be - how boring), but I really don't think clothing or style should matter.
Why is it such a huge deal if someone isn't matching? Or if someone has a hole or mark on their shirt?
People have off days, you know. Maybe, their mind is elsewhere, but even if it isn't, if they don't mind, then, why do you?
Really, there are much more important things you could be thinking about and devoting your energy towards.
Regardless of what I'm wearing I expect to be treated respectfully. People are much more than their wardrobe.