I'm a clearance rack shopper except when it comes to jeans, then its mostly levis. I find a lot of nice tops for anywhere from 8 to 20 a piece and buy multiple colors of the same style too. I rarely go clothes shopping though. And as for purses, I have a number of those, but I still have a hard time parting with my old trusty brown leather bag that I've used for years.
And no, I don't feel pressured in the least to have designer clothes. The people I am around can generally appreciate a good deal and if you look nice, then who designed it doesn't matter.