I'm coming into this thread late, so maybe everything important has been said already. I count myself in the camp that doesn't strive for pretty, either in my overall look or in individual pieces. I think of pretty as one of those words that describes your looks, primarily, like beautiful - in other words, the things that are mostly genetic and you can't do a whole lot about, anyway. I was an awkward kid, lanky and too tall and not particularly graceful, so I was never pretty. If I strive for anything with my clothes and makeup besides aesthetic self expression, it's to look attractive, or put together. Someday I hope to become a jolie laide, or perhaps "a handsome woman".
I do think pretty has become loaded for lots of us with associations with traditional femininity and all the baggage that comes with it. Pretty doesn't mean weak, these days, but neither is it particularly closely associated with powerful or strong or any of those words.
Of course, if someone compliments me with pretty, I will be pleased and say thank you, taking it in the spirit in which it's intended.
Janet, there was a kerffuffle recently about a company trying to redefine the word MILF for an advertising campaign - I can't remember the details unfortunately, what item they were selling. But it was very wink wink nudge nudge and they got a lot of grief for it, justifiably so, I thought. In a casual situation with a friend it's more of a compliment - hey, you're hot, I can imagine lots of people wanting to have sex with you. We're so weird in this society about older women and sex; we have to talk about cougars and MILFs as if a woman being sexually attractive over the age of 30 is so shocking.