In the interests of both decency and consideration for the aesthetic sensibilities of the other passengers, I would prefer not to have my skirts blown up to my waist. I would also prefer not to have my nice stroll hobbled by needing to hold my skirt down.
I can confine myself to trousers and straight(ish) ankle-length skirts if necessary, but I am going in August and would normally bring a couple of knee length skirts to cope with the heat at my destinations (NYC and Austin).
For me planning what clothing to take is part of the excitement and anticipation of travel. I travel solo and light so it takes careful planning. (Or so I tell myself) It also makes a trip over 7 months away real.
I posted some of this on the Cunard board as well, but I thought I would also ask the fashion experts here.