In response to:
Two examples please!
Going out somewhere nice.
Just going for a coffee.

First date... Well I would be nervous so for coffee i would wear my favorite jeans that I feel really comfortable in and a top that flatters me without being to revealing.
Somewhere nice.... I'm going to be even more nervous so I'm wearing the outfit I've received the most compliments on in the past, I want to be able to focus on the date and not worry about if my new dress looks good or not!