For a very long time, I went without a bra 95% of the time or more. I have small enough breasts not to need the support for comfort, although I do have very prominent nipples. I got used to just ignoring the looks I get from those. With small breasts, the attention doesn't seem to be that bad. However, I've recently noticed that they seem a little more loose, for lack of a better word, and I've started wearing bras much more often (about 80% of the time) in order to prevent them sagging too much later in life. I don't mind too much; as long as the bra fits properly, it's not uncomfortable.
If you want to wear one, but you think they're uncomfortable, they're not fitted properly. And every woman will have some brands or styles of bra that will never fit properly. Get yourself measured (many department stores will do this for you; walk up to the cashier in the lingerie dept and ask if they do that) so that you're at least getting the right size, and then ignore appearance long enough to find a style that works for you. Once you find a good brand/style, then you can look for one you like the look of.
As for bralessness being healthier, I'm not sure. I know that it's bad to have a bra that cuts off circulation, and I know that wearing them 24/7 has been linked to increased risk of breast cancer in at least one study, but as long as they're fitted properly and you don't sleep in them, I don't think there's any serious medical reason not to wear them.
All of the above is only my own opinion, and is not intended to be judgmental or dismissive of anyone. I hope it helps!