First date -- feel fun or feel pretty?

Question

I know, this is silly. I'm going out tomorrow night on what is potentially a first date and I've been wondering all day.
Should I go with feeling funner or feeling prettier on a first date?

Outfit A is a non-baggy red-gold-burntbrown plaid/flannel button up shirt, with a gold griffin print on the back, over a cream tank, with brown pants and converse.
Outfit B is a brown/cream/tan shortdress/minidress over the same brown pants and nicer shoes.

Outfit A makes me feel like fun. Outfit B makes me feel prettier. Both give me a bit of a confidence boost, because they bring out my better areas and down play the not-so-good. We're going out to see 300 and eat dinner. On one hand, I don't want to seem too girly, but on the other hand, I don't want to seem like too much of a tomboy. You know?
Please, help?

I am looking into it a bit much, but I do that when I'm nervous.

This is actually my first date in a few years, and I like the guy (but we've only talked on the phone so far), so I am sorta sweating the details...

Answer 1

Considering the environment (dinner, movie), I'd personally suggest what you describe as "feelin' pretty." However, I do think that you are looking into this a bit too much. Relax and just have fun. Enjoy yourself. Don't get caught up over things that don't matter so much like your outfit. As long as you dress appropriately, that's all that matters in that area. Concentrate more of your attention on what you will talk about, how you feel about this person, and what your next moves will be (if any).

Answer 2

I think of it this way, it's a first day and you're trying to impress the guy you like. Feel pretty while you do it since you would be fun either way! After luring him in with how pretty you are and getting to know him better, and becoming more comfortable around him you can ease him into your more fun side and you can wear more comfortable clothes then. Save fun for when you need to be practical, Dinner and a Movie is ideal for something a lil sexier because you don't have to worry about running around everywhere or messing up your hair! Go for it and good luck!

Answer 3

You probably should wear Outfit B. First impressions mean a lot to some guys and looking nice is one of them. If anything though, don't be nervous. Have a good time and I hope everything works out well for you. : )

Answer 4

I would want to feel fun. Either way, you will probably look pretty and guys don't know much of the difference between the outfits, he is just gonna be happy that you showed up. Any way, your first date should be fun and light hearted so I would want to wear something that helps me feel that way.

Answer 5

I suggest that you should wear outfit B instead of outfit A

Answer 6

unless you're going to be running around or doing an activity (i.e. amusement park, bowling, etc.) i say go for the pretty one. although you're going to be sitting in a dark theatre for 2 hours, you're also going to have him look at you during dinner, so you want to feel pretty. i understand your nerves but just relax...you'll have a great time!