Dressing for a date isn’t just about looking good, it’s about communicating information. Your accessories – watch, belt, etc. – are a chance to communicate your sense of style to a potential girlfriend.
It really doesn’t matter what your look is, so long as you have a look and wear it confidently.
Spend time honing your style. All those lost nights at the bar with your buddies playing Golden Tee need not amount to nothing. Figure out your look. Spend a little dough. Try it out. And when the time comes, you will be ready. (For women, not for that dog-leg par 5.)