The question has been asked by several of our customers "Should I wear a suit on a first date?" Some people always dress up on a first date. If you are coming directly from the office to have a dinner date, then your work attire does help to define you. But if you don't wear a suit and a tie regularly, don’t wear this kind of attire unless you are going to a fancy restaurant or the opera. You don’t want to look like someone you are not and most important you have to feel good.