When a woman goes on a first date with a guy, she looks in the mirror about 20 times before finally walking out of the door with butterflies going crazy in her tummy. It is a big deal and there is nothing more important to a woman than to look good for a gentleman she has just recently met. Obviously the guy is already interested in you if he has asked you out on a date, but that doesn't matter, a woman can never impress her man too much, or her man-to-be at least. She has to look good at all times, but it is true when they say it is the first impression that counts.
In order to determine what you are going to wear, you have to take the location into consideration. Where is he taking you for your first date? If it is a fancy restaurant, you won't wear old jeans and a baggy T-shirt, but something more eye-catching and presentable. Where as if you are just going to grab a burger and head to the movies, you should dress more casually. Casual doesn't have to mean boring, shabby or un-sexy; you can still have his mouth gaping at the site of you while dressed casually. In this case you would want to wear a sexy pair of jeans,(tight jeans if that is what you prefer) and a pretty top. Remember that you don't want to look too sexy; it's only the first date! If you are going to a fancy restaurant, try something more formal. Maybe a nice pair of pants with a gorgeous matching top and high shoes, otherwise a knee-high skirt with a tighter fitting top. Take the weather conditions into consideration too!
Most importantly, don't wear something that is not you! Wear what you feel comfortable in, if it is baggy clothes you prefer but he is taking you to a fancy restaurant where you have no choice but to look smart, make an exception just this one time but later explain to him that it isn't really your thing. It is important that you reveal a bit about yourself on your first date, whether it is with your favorite bracelet, necklace or ring, wear something that you always wear; do not change your appearance for the first date otherwise that is what he is going to expect from you all the time!
Do not wear your most expensive brand name clothes to your first date with this guy! This might just put him off because he will think that your taste in clothes is a little over-the-top. You should also do your best to show the romantic side of you, and wearing pink is the best way to do so. A pretty pink top normally goes with anything, so if you have something like this in your wardrobe, put it on! As long as you are comfortable you have nothing to worry about. You shouldn't have to sit there wondering if your jeans are going to split because they are so tight, or wondering if you have dropped a cup size because you put on your smallest bra to give you the most cleavage, be yourself and dress in whatever makes you feel good about yourself and not something that is going to embarrass the guy!