Originally posted by Raven
My $200. hairstyling, with highlights, costs more than my six dollar tee shirts. I spend more on pedicures than I do on clothes. The two carat diamond on my finger goes as well with sweats as it does with a gown...which, by the way, I bought for my first Vegas adventure....and, recently, just sold on Ebay, with the tags still attached.
What matters from the above?
If you're hardly a slob, what point are you trying to make about other webmasters?
You also talked about shopping at Value Village, as if that's a crime against humanity. it is; but, that's beside the point. 
Looking like you've bought the cheapest, most ill-fitting clothing from 1979 and had left it on your bathroom floor for 3 days before wearing it IS a crime.
I think your third point was probably the most interesting. To some, appearance is ALL that matters. Hardly a way to judge whether or not that person is someone with whom to do business. To others, appearances are deceptive. The guy who is wearing a torn sweatshirt, with shaggy hair may be someone for whom you want to do business.
I think given the choice I would rather talk to someone dressed a little more presentable first.