Anything that would say more about you than you are willing for the other person to know should not be worn on a date.
You want to make a good impression on a date, and look clean and tidy, so don't wear anything that has been worn recently and not washed, don't wear anything that needs ironing and hasn't been ironed. Don't wear your old shoes which are falling apart.
I think it depends on where you are going on your date.Dress appropriately for the destination, whether casual or formal. I agree that clean, ironed clothes and decent shoes are a must for women and men. I think clothes for a woman should fit properly and not be so tight that that a shirt is wrinkled across the front for instance.
Unless you plan to change your wardrobe what is the point of trying to look one way to "impress" someone only to revert back to your natural self once they become emotionally invested in you. Naturally you want to dress appropriately for the event or occasion. (You would not wear jeans and a t-shirt to a 5 star restaurant). Being yourself saves everyone time. People are sick and tired of "bait & switch" tactics. Too often we hear someone say, "He or She is not the same person I fell in love with."
Ultimately we are all looking for someone who will love and appreciate us for who we really are. Always be true to yourself!
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