Putting your best foot forward is definitely an important part of dating. One think you don't want to do is create a false impression. Dressing sharp will attract women. However, if you're acting like someone you're not, you're likely to attract a woman you have nothing in common with.
When I was in the executive world, I dressed the part. The right watch, the right suit, the right tie, and the right car all drew women. The problem was the kind of women it drew. In the club world and corporate world, dressing sharp is half the game. However, it's much better to upgrade while being consistent with who you are than to try to be someone you're not. That's why I wear a Timex instead of a rolex now.
The best solution I have found is to become involved in whatever inspires you. That way, you're likely to meet someone who shares your passions. Dress nicely, but appropriate to that activity. That way, the problem takes care of itself.