What an interesting discussion! I acknowledge the problematic aspects of 'pretty,' but I also think it's possible to be a feminine feminist, aka still appreciate certain actions/attitudes/characteristics/etc. traditionally associated with women while abhorring patriarchy, sexism, and misogyny.
With that disclaimer out of the way, many of the clothes I'm drawn to probably fall in the pretty category: I like pintucks and bows and muted colours and soft fabrics, among other things. I'm not consciously aiming for pretty when I shop, I'm buying things I love, but the result is a closet with quite a few pretty clothes, and it makes me happy.
*Being* pretty seems to be a different matter. On a day-to-day basis, looking pretty myself is not one of my top goals (being true to my style persona, comfort, and weather appropriateness are probably my big ones), but I certainly enjoy the days I feel pretty! I spent my adolescence, from age 12 to about 18, believing I was ugly, deeply ugly to the point that there were days I didn't want to leave the house because I didn't want to inflict myself on the public. That was not a fun time! Around age 18, I decided I was sick of feeling that way, and began a conscious campaign to improve my self esteem, and thank goodness it eventually worked, because that kind of self-loathing is exhausting. I do aim for pretty during 'events' when I'm seeing family/friends/etc. or at something like a party or gathering where I'll be meeting lots of new people or for a date, because I feel most confident & outgoing when I've got my 'pretty' armour on. When I want to look pretty, make up is definitely my first focus, then hair, then clothes. I'm also aiming for 'interesting' though for those events!
I'd prefer to be perceived as beautiful vs pretty, but considering I have a number of 'cute' characteristics, I think pretty is a more realistic aim. hehe I definitely take pretty as a compliment, although that OED definition seems a bit harsh. I suppose as a legacy of those ugly duckling years, I'm always just thrilled to feel extra good about myself, and I take joy in any compliment. If I could pick anything, though, I'd love to be striking! Attractive isn't really a word that I use to describe anything, so it's not on my radar. Perhaps I use the word 'pretty' in the same context others use 'attractive'? I equate it with looking my best.
I don't know if my ramblings made any sense, but I suspect I'll be mulling this over for awhile yet. Thnx to Una & Catnip for starting the discussion!
P.S.: Another Aragorn girl registering her vote! ;D