Most Helpful Guy
Well, you're probably meeting in a public place and getting dragged away by the police doesn't make a good first impression (and I say this from personal experience), so disregard that.
It really depends on where you're going. If at a seaside bar, wear something casual. If at a nightclubish spot, something more dressy.
You don't want to look like you're on your way to the office, but also don't want to look like you're trying to support a meth habit standing on a street corner. So wear something comfortable that accentuates your best qualities.0