Angie hit the nail on the head for me. For example: I really do not like Coach bags that have the monogram printed all over it. To me, that basically feels like the person who buys the bag is paying for the privilege of wearing a huge advertisement. However, I don't mind logos that are part of a design - for example, there was a discussion somewhat recently on the forum about some Tory Burch flats that had a metal buckle with the logo; to be honest, because I'm not that familiar with the brand's logo, I just thought it was a pretty buckle and didn't think anything of it.
I'm a bit more conservative as far as wearing labels myself than I am towards what I prefer on other people. At this point in my life, I don't feel comfortable with my visible labels being big enough to read unless someone is standing within a few inches of me. One of my pairs of glasses has the brand name printed on the sidearm, but you literally have to have it within a foot of your face to read the text. My Franco Sarto handbag and Armani Exchange jacket have very small visible logos, too.
I actually considered purchasing a goooorgeous mustard Kate Spade handbag that we were looking at during the Seattle meetup at an outlet store, and still am debating. What held me back was that even though the logo is tasteful and small, it's still very recognizably a Kate Spade bag, and I need to think hard about whether I'm ready to make the step of carrying a recognizable, though impeccable quality, designer bag. I *know* there are people around me who would view it as being silly and pretentious, regardless of how long the bag holds up over time, or whether I bought it on sale in the first place.