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Ask him if any other girl you know is going and then shop for similar clothing...at least that way you know you've got someone in the same boat as you.
Different schools and chapters are used to different things. For a lot of the fraternity formals at my school the girls wear cocktail length dresses, not long dresses. They buy those for their own formals. I'm actually getting one from victoriassecret.com. It looks like a party/cocktail dress, but it's about $50.
Forever21 is a great place to buy dresses for cheap...but be aware of their exchange policies.
For your price range I would try both of those first if a shorter dress is appropriate. If you feel comfortable doing so, ask him to ask an older brother what their dates always wore...long or short.
He SHOULD be paying...it's inappropriate to ask someone out and then expect them to pay.
And as for the shoes...I would wear flats...it's polite and shows consideration for him. Flats will probably be cheaper as well...you can find them on both the sites I mentioned.
And by the way...accessories and shoes can make the outfit.
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