What to wear on a first date? Of course depends on the situation, time, guy... But talking about the classic evening date - dinner, restaurant - little red dress. But not too little. It should be nice, attractive but not saying - I do my best to be undressed tonight. Fashion accessories are telling you have a good taste. Natural beige make up is telling you woke up like this and no need to have tons of make up. Pearl earrings tell you are smart and intelligent. You look gorgeous! Cheers!