What To Wear On A DateLike it ? Share it:Share it:What to wear on a date? As a lady, this is the pivotal question. I don’t want to look too smart, but equally being underdressed would be an embarrassing first impression. I want to look classy and sophisticated, without representing something my grandmother would wear. What we tend to forget is that men have the same problem. Granted I’m sure you don’t spend days and days planning exactly what to wear, but it must cross your mind?