To wear a skirt in a dream, denotes to the feminine aspects of your personality. Probably you are trying to express yourself more as the potential female. The length of the skirt also tells much more about a dream, for example the short skirt would send the sexual message while the long one shows the conservative views of the dreamer.
Dream dictionary: Skirts dream meanings
…young woman), came Martha Martha wearing one of those short skirts so popular with the depraved aristocracy, and her feet bare!””Only her feet?” I exclaimed. ” Was that all?””All! My companion sighed reproachfully ”all! And was not that enough, and more than enough? Bare feet! Oh, how indecent! But I can assure you, much though the devil tempted me, I did not look twice at them. I kept my eyes glued to my cup. And her mother her mother! Oh, how shocked she was!’ Martha!’ she screamed, clutching hold of me for support, ‘Martha! Are you bereft of your senses? Whatever has come over you? And before Mr. Simpson, of all people!What mortification!’ Well, ma, neither of you need talk!’ Martha retorted, her face one broad, shameless grin. ‘Neither need pa, for he is dealing out the groceries in just the same plight. Oh, what a day…
…Dreaming that you are in the path of a whirlwind, foretells that you are confronting a change which threatens to overwhelm you with loss and calamity. For a young woman Dreaming that she is caught in a whirlwind and has trouble to keep her skirts from blowing up and entangling her waist, denotes that she will carry on a secret flirtation and will be horrified to find that scandal has gotten possession of her name and she will run a close risk of disgrace and ostracism….