First impressions are important too, no matter how much you deny it we're all shallow. There's no doubt that his chances are much better if he's looking good then dressed like a slob. Like I said before, if you can rock it, just wear it because it's all about confidence.
Yeah, but there's a difference between dressing smart and dressing to impress - wear what you feel is
your best, but don't go dressing to emulate some imaginary ideal man, because it either doesn't exist or is beyond your reach. Just don't go out and buy a new outfit - wear what looks nice, but don't dress as what you
think she will like; because chances are, it will be both out of your comfort zone and not quite what she would imagine either. Seriously, you're just putting extra pressure on yourself, when it seems you look pretty cool anyways (but that's the whole of my point with appearances to begin with...). Just be comfortable with yourself - your outfit means nothing if you're comfortable in it. After all, if we were out for a cool outfit, we would take a catalogue out on a date