One of the more famous skirt-blowing scenes in recent movies is the scene from Bruce Almighty from 2003.
A few years later, pin-up artist Mike James made an animated gif of a skirt-blowing scene using rotoscoping. Rotoscoping is where an animator draws a cell for each frame of a live film or video. Sometimes the animator even traces the film frame directly. James calls his animation "Dress Up", and you can see it directly from his site
http://xxx.jamesart.com.
Have a look at the attached video and screen caps from Bruce Almighty along side James' animation. I think we found the live video he used for rotoscoping.
For me, the key to matching the two up is how the women try to get their dresses back under control.
The animated gif is right next to the screen caps. I can't seem to figure out how to get the gif to play its animation without opening it in a separate tab, though.