Oh I really like this question, this is an interesting topic.
Ironically, what I look for in what I wear is a look that says I'm not trying to achieve any look with what I wear. Does that makes sense? I try to project the image that I'm not trying to project an image. I want to look presentable and nice, but not overdone or too polished.
When I'm trying to attract someone, I try not to look any different than I normally look. I may wear my sexier clothes, but I want to honestly convey who I am and how much work I honestly put into dressing myself. And when I look in the mirror half way through the day, I want to feel like myself, not like I'm playing dress up or pretending to be something else.