This is an interesting question. I've been thinking about it for a couple of hours, and I think I'm going to answer with a hesitant "no". If it looks good on me, I feel comfortable wearing it, providing the situation I'm wearing it in is appropriate for the look. For example I'm OK with showing cleavage, so long as it's a dressy evening event and my skirt isn't too short. Or high heels and skinny jeans -- a look which I love -- is something I feel perfectly comfortable in for a Friday night out at the pub, but wouldn't be caught dead in for picking my kids up from school.
But I don't think this was always the case. As a young woman I wore nothing but pants, and it took me quite a while to get used to wearing skirts and dresses of any shape when I first started experimenting with them several years ago. At first, even though I could plainly see that a skirt was flattering, I still felt weird in it -- almost naked, as you say. That's a good description. But since I liked how it looked so much, I kept doing it. Wearing a skirt with tall boots made me feel more comfortable, so that's how I desensitized myself. Now I wear skirts all the time and I'm *almost* as comfortable in them as I am in jeans.
