Many women wear trousers or jeans today, and so a dream that either men or women have featuring a dress or skirt may suggest a desire for both sexes to express their feminine side. It could also be a symbol of the mother and the security of her nurture. The colors and length of the skirt will say a lot about what is being done with sexuality in a social sense. A woman wearing trousers may—in line with the idiom ‘wear the trousers’—express a fear of being dominated by a woman. In general, trousers in a dream suggest masculinity, whilst jeans suggest socialized sexuality.
If you are wearing shorts, you may be outgrowing former pleasures and need to look to new experiences for your entertainment. On the other hand you may just be longing for the carefree days of holiday summer sun.... The Element Encyclopedia
Vision: In men’s dreams: seeing a beautiful skirt means winning the favor of a charming woman. Seeing a very short, tight skirt: you will meet a frivolous woman. Seeing a wide skirt: you are having an affair with a woman and the wheels of gossip are turning. In women’s dreams: seeing a wide skirt: you are going to be faced with an embarrassing situation. Seeing a short, tight skirt: a man will make improper advances—but through no fault of your own. Seeing a worn-out skirt: right now you are not having much luck with the opposite sex—get ready for a disappointment. Seeing a beautiful skin: good luck with the opposite sex. See Clothes, Pants.
Depth Psychology: A skirt, like pants, is a sign of your erotic desires and needs—a slip would be even more so: you clearly are ready for romance.... Dreamers Dictionary
To dream that you are wearing a skirt, represents the signals that you are conveying or sending out. Consider the condition of the skirt and you’ll get a clue to the impression you are making on others.... My Dream Interpretation
The meaning of this dream depends on the sex of the protagonist. For a man, a skirt in dreams denotes his attraction to a woman; a short or tight skirt advises caution with certain companies; a long or wide one represents excess of morality; and if he is wearing it, gossip and public humiliation.
If a woman dreams in skirts it means that she will soon receive an unexpected visit; if it is beautiful, success in her relationships will be assured; if it is too short she should be aware of bad companies; and if it is too long she will be the subject of acquaintances’ gossiping.... The Big Dictionary of Dreams
This dream omen follows the same pattern as do the fashions in relation to the economic cycles; if your dream featured short and/or tight skirts, it is telling you to be prepared for a season of financial strain; long and/or full skirts prophesy an increase in material wealth.
Otherwise, see Clothes and Colors.... The Complete Guide to Interpreting Your Dreams