Not having much luck persuading windows movie maker to produce thumbnails (mostly because all the files I tried played as a featureless green screen) so you'll have to put up with descriptions I'm afraid.
1) Girl walking along street trying to hold her skirt down (and failing).
2) Skirt blowing scene from Dr Dare a "carry on" style film from the 70s (I think). A girl walks up a set of stairs on a cruise ship and nature does the rest.
3) A reporter is trying to conduct an interview out of doors in a dress. She should have paid less attention to the interview and more to the dress (although I'm kinda glad she didn't). From a bloopers show as I recall.
4) A bridesmaid walking up a set of outdoor stairs discovers the effect of an updraft. From AFHV.
5) I think this one is from Spanish TV. A waitress in a short skirt serving customers out of doors. Extended skirt blowing.
Cheers
Des