Most Helpful Girl
It depends on the date. I'm not going to wear a gown to a picnic or hike, obviously. But, generally, I try to dress as formal as the occasion allows. My general attire is more business than casual (say what you will, I think business pants are comfier than jeans), so for your generic type of dates (movies, restaurant, coffee date), I'll probably be in some trousers and a blazer.
Most Helpful Guy
What's the point in faking how you usually look for the first date?
Wouldn't dressing casual be best for the first date anyways as it shows the other how you usually dress and what they dress like usually, it's like a 1st step to knowing one another better.