I've been in love with thigh high socks for a while now, and finally took the plunge today (because American Apparel is a block from my house. "Have you shopped with us before?" "Uhh..")
Anyway, I've been thinking about them a lot and whether or not I should take the plunge (obviously my reasons convinced me to) and I realized they are a pretty good idea afterall. Why? They're like the 3-in-1 for your legs.
Obviously the first way to wear them are ... as thigh high socks! Don't let this trend keep you away though, there are plenty of ways to wear them without looking like a schoolgirl or a stripper. It's really all about the shoes here. Big towering heels, and you get stripper. Little mary janes? Schoolgirl. The best way to play this trend off are with simple flats, any sort of boot (tall or short), or chunky summer sandals, with or without a heel. They keep the proportions balanced, and don't have any negative image associations.
If you get the right kind, you can pull them ALL the way up your leg, and when worn with a skirt, dress, or longer shorts, they transform into tights. The perk? Why not wear tights? You avoid that horribly gravity dilemma between your legs completely. And because they are socks, they come with additional warmth and thickness, and that cute sweatery appearance too.
The longer your socks to begin with, the more satisfying "scrunch" they make when you push them all the way down. This is best to do with boots - you get wonderful warmth, and that legwarmer look around your ankles. You can keep the scrunch from ankle to knee, or push them all the way down to the bottom. (For a "real legwarmer" look, fold down your sock from the hem, and pull that over your boot).