The common misconception about knee-high and thigh-high socks seems to be that they belong either on weird school-girl fetishists or, umm, hookers. To which I say: You're kinda right. But those Roxannes and Lolitas and whoever else are also known to wear skirts. And dresses. And blouses. And I think they have hair, too. As always, it's all what you choose to pick out and what you pair with it.
But maybe you're shy. The extreme sexualization of females in knee socks is sadly undeniable. On that note, the extreme sexualization of females showing any centimeter of thigh is sadly undeniable, too. But there's a way to remain ladylike and stunning in the tricky legwear.
Prada's spring 2006 and fall 2007 collections should always be your first go-to visual tutorial for knee-highs and thigh-highs. Miuccia Prada prominently featured slouchy heather-gray thigh-reaching socks juxtaposed with clean, neutral-toned outfits on effervescent-skinned models with neat ponytails last spring. She finished it off with open-toed, wedged sandals and those near-flawless handbags Prada's come to be known for. It was elegant, refined, but still somehow fresh. Prada's fall 2007 line featured colorblocked, jewel-toned, footless knee-highs—again paired with open-toed, heeled sandals. It was a fantastic way of throwing in some color—mostly of the mustard-yellow variety—in outfits with mostly blah fall grayscale.
While I never had much luck hunting down a pair of those slouchy gray socks—they were naturally sold out everywhere—the closest I've come is SockDreams.com's MP Ribbed Wool OTKs ($16). The bountiful website also offers their version of the toeless colorblocked variety, the Harajuku Toeless Over the Knee Socks ($16). The best knockoff can (surprisingly) be found at American Apparel stores, which seem to have nailed the color combinations dead-on—and all for $12 a pair.
If there's one gal to look to for inspiration, it should be British television host and Arctic Monkey girlfriend Alexa Chung. She's been stepping out lately in knee-high and thigh-high socks, matching them with short shift dresses and cutesy frocks with front-tie bows. But other celebs such as Peaches Geldoff, Agyness Deyn and even Posh Spice have been seen in their own varieties.
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The idea should be to not be too matchy-matchy—gray-colored socks seem to be the most wearable without being too corresponding. It's the same idea that your curtains, bedspread and wallpaper border shouldn't be of the same print. It ends up looking cheap. Costumey. Old-fashioned.
Wear them with slightly looser, unstructured dresses. The saggier socks go with the sloppy-chic look. Socks with a tighter fit, conversely, go with a cleaner look—so wear a (slightly) more-fitted dress.
The best way to ease yourself into the hosiery would be with some tall boots: Have the socks peek out just barely over the top of your favorite pair.
And it probably helps if you're slim and tall. Which regrettably goes for everything these days, fashion or not.