Dating can be so much fun. You meet new people, try new food, do new things and it can be so exciting! One of my favorite parts about dating is the process of getting ready (at least if it's a date I want to go on!). I love picking the perfect outfit to wear, deciding how to do my hair, and making my makeup look pretty. The best part is when your date picks you up and says "Hey you look great!" Especially on first dates, I want to look smashing but not like I tried. It's a skill to be mastered, but not one that's hard to learn.
When I go out on first dates or a series of first dates the look I always go for (contingent of course on the activity for the date) is looking great without looking like I tried. If you try that route for looking beautiful on your date, I think it intrigues the guy a bit more and gives you more of an upper hand. (If he sees he doesn't have to work for anything that could turn into a problem).
The best way to achieve this look is with a great pair of jeans. Jeans are a great way to make you look stylish but casual at the same time. Depending on what you're doing (e.g. nicer dinner, a concert), a good heel looks awesome with long boot-cut jeans. (If you're just going to a movie, a really high heel might not be your optimal choice)
The kind of tops you should wear shouldn't be loose t-shirts (unless the dates continue in which case you can definitely loosen up a bit), but form-fitting tees are quite flattering. Your top can be more dressy if you're wearing jeans and the only thing you should avoid on the initial few dates are too loose of a tee and too dressy of a top. Of course, remember all these guidelines are revisable based on the date activity and the guy himself.
The most important thing to remember on a date is that looking beautiful isn't synonymous with looking slutty. The kind of guys that are worth dating and pursuing will want to look past physical attraction and find something deeper. You don't want to wear that super-low-cut top or the leather mini skirt. That kind of clothing shows disrespect for your body and if you disrespect your body, what's to stop your date from thinking or doing the same? You want your date to want more than your body and the first way to ensure that is by dressing modestly. If you want to be truly beautiful on your date then dress classy, sophisticated, comfortably. Looking beautiful is dressing so that yes, you are attractive physically, but also so you are attractive on a deeper, more substantial level. Dating is a fun and exciting adventure so you want to put your best self forward and that doesn't mean giving it all up by the time the salad comes.
Now when that cute guy from the bookstore asks you to meet him for ice cream the next afternoon, you'll know what to wear and what's actually important when looking beautiful on your date!