Dreams dictionary: Skirts
Dreams dictionary: Interpretation 1
To dream that you are wearing a skirt represents the signals and hidden messages that you are conveying or sending out. It also symbolizes femininity and your sense of sexuality. The dream may also be a metaphor on an issue that you are "skirting" around over and not confronting head on.
Dreams dictionary: Interpretation 2
If you are a man and dream that you are wearing a skirt, then it indicates that you need to acknowledge the emotional aspects of your personality.