Steven Den Beste asked the rhetorical question, “Can wind lifts actually happen outside anime?”
1. Yes, they can.
2. If one is unwary, if one wears a badly-engineered or naturally flippy skirt, and if one does not wear a slip or shorts under one’s skirt. (And as an ex-schoolgirl who wore the classic plaid jumper, most of us wore our shorts underneath during most of the year. Sorry, guys.)
3. However, most girls learn early that one has to watch out for both wind and six-year-old guys; and they take countermeasures like holding the skirt down, or wearing a longish jacket/raincoat, or just not wearing a skirt on an overly windy day.
4. Bear in mind that if the wind is really that strong, you don’t really want your legs or hiney experiencing wind chill. It’s also probably pretty cold on the hiney, even with the skirt in its proper place. (Hence the current popularity of wearing leggings under skirts in the winter, or even shorts versions of long undies.)
5. In addition to being supposed to be worn significantly lower on the leg than anime girls do (and to be fair, I have heard that a lot of girls in the US, past and present, also have been known to hike up their skirts when they get out of sight of home), the classic plaid jumper pleats are engineered so as to hang down rather heavily and thus protect modesty. They feel pleasantly flippy to the wearer, but they are surprisingly difficult to mess up.
(The same is true of the short, tailored Victorian men’s kilt, from which the classic plaid jumper distantly derives. Since Scotsmen don’t wear any undies under their kilts except their shirt-tails, which of course do count as underwear from a medieval point of view, their Victorian tailors had a vested interest in protecting their tender bits from the cold north wind.)
6. So in real life, it’s a situation full of embarrassment and chagrin. Your organization and presentation have failed, as well as your attempts at modesty; this is a predictable wardrobe malfunction which you failed to prevent. Also, you have just exposed yourself to the rigors of the weather, as well as your neighbors. Of course, some woman somewhere is always going to be doing something like this on purpose, to attract attention, so one may also be anxious to establish that it was a true accident and not artifice. (“Why, yes, I’m an idiot, not a slut.”) Chagrin, chagrin, chagrin.
7. Now, there is the special case of “walking over a hot air grate in a city.” Most women would not actually do this while in a Marilyn Monroe outfit, because that entails wearing high heels. We have a lot of fear of our heels getting stuck in grates, and of accidental damage to the shoes from hitting the metal wrong. But it is pleasant to walk over a hot air grate in the fall or winter while wearing a skirt, if one is wearing a coat long enough to hold down the skirt, or if the hot air is not overly powerful. So as one would expect, the Marilyn Monroe version of this nice warm-up moment in the city is pure fantasy. But it’s an amusing fantasy.