Are there any rabbinic opinions that allow women to wear loose-fitting pants for sports in which wearing a skirt is problematic? For example, in skiing and windsurfing, the wearing of a skirt is actually immodest - both because it can fly up if one falls, and also because it attracts tremendous attention (due to being such a strange way to dress while engaged in these sports). Thanks for the answer!
Shalom U'Varacha The prohibition against a woman wearing man's clothing is that it is immodest and a woman will come to have undue contact with men. Rav Yisraeli was asked about women's loose fitting pants that are made specifically for women and he allowed it in cerain circumstances. For example on hikes some poskim allow women to wear pants and a skirt over the pants. I think that we need to ask whether there are other aspects of these sports that may be immodest, such as mixing of the sexes etc. However if it is all done in a modest atmosphere then it would be permitted to wear pants with a skirt over. Kol Tuv Gideon Weitzman