OK, first things first:
Legolas: cute
Aragorn: handsome
Boromir: hot
What can I say? I find Sean Bean extremely attractive, especially in LOTR costume.
Back to your actual question, i.e. what do I aim for in the realm of pretty/beautiful/attractive? Well, I think beautiful is out of my reach, even on a good day. I do aim for attractive and/or pretty, although my idea of pretty might not be the same as the next person's. For example, lots of women think lace is pretty. I don't care for it. Once in a while, I will see a lacy item that I think is quite nice, but in general, I think it's kind of ugly. So I wouldn't put on a lace item to make myself look prettier. To be honest, I'm not sure that ANY item of clothing does a lot to make you look prettier, because clothes don't really affect your face. When I think "pretty", the focus is on the face. What DOES make me look prettier is mascara and lipstick. I wear those things most days, which demonstrates that looking pretty is at least reasonably important to me.
"Attractive", on the other hand, goes farther than just how your face looks. It involves not only the whole body, but how you present yourself -- so your demeanour, as well as your entire outfit, play a role. I guess I do want to look attractive, because I try to find outfits that are at least somewhat flattering, but honestly? Looking cool is more important. I feel silly using that word, but there is no other I can think of to express it.
I guess the question is, would you rather look hot (sexy, attractive) or cool (hip? insouciant? -- aaargh, there really is no other word). I know where I want to be on the spectrum. Whether or not I achieve it is debatable.