I'll chime in re: having a partner and subscribing to the belief in "pretty." Hmm. I am vain. I always have been. I think I'm the kind of person who *can* look pretty if you catch me at the right angle, with the right light, on a good hair day, etc., but I don't have that symmetrical willowy model-esque conventional beauty so valued in our society. I've always been insecure of my looks, and when I was younger, I tied a lot of my self-worth to whether men (or a particular man) found me attractive. Just being totally honest here. I had (and still have remnants of) a lot of hangups about attractiveness and self-worth. I am the child of a perfectionist and learned to turn a critical eye on myself from a very young age.
Now that I'm older, I know I will rarely be "the prettiest girl in the room" (even if I ever was), and I now realize that it's not important. At. All. Thank goodness! I do want to convey some type of attractiveness, and at this stage of life, whatever word the onlooker wants to use to label it, I'm OK with that, whether it's pretty, cute, beautiful, striking, or even though I cringe at the word being applied to me, handsome (sounds too mannish to me). These words are all defined by the user -- like Una says, one person's "breathtaking" can be another's not so much.
My husband and I have been a couple for almost 17 years, and he still compliments my appearance (as well as other qualities) on a regular basis. I do still want to "look pretty" for him as well as for me, but I don't know, is "pretty" the right word? I'm actually trying to remember the last time he used "pretty" when he complimented me, and I can't come up with it. He has used beautiful, gorgeous, sexy, hottie, etc.
I guess I do strive a little bit for "pretty" in how I look, but not "pretty" head-to-toe. I will wear a pretty top or a pretty pair of shoes, or maybe even my hair will look pretty. I dare say that when my husband and I go to a more formal event -- a wedding or an event with his business colleagues, my "pretty" style comes out more, and the rock'n'roll side takes a back seat. But my ideal preferred aspirational style mixes a little bit of pretty with other things that seem more interesting and more true to my personality and my identity.