"makeupguru" wrote:You should wear something that matching the season. You don't want to be wearing a short skirt or dress when its 20 degrees outside. Also something that fits you and your personality. If you normally dress simple, don't be putting out a wedding dress on the first date. And lastly, wear something that matches what you will be doing on the date. If you are just going to dinner, than you can wear whatever you want. But if he/she is taking you to the zoo, I would leave the 6 inch pumps at home.