I’ve always thought that when a woman wears knee socks, she’s wearing them either for warmth under long pants or to look like a Catholic schoolgirl—so imagine my surprise upon seeing a photo of Carrie Bradshaw rocking a short skirt and over-the-knee socks while filming an episode of Sex & the City and not looking like a roleplay fantasy. She actually looked very stylish! (I know—not surprising for SJP.) Check out her outfit here.
So now I’m actually looking forward to bringing my over-the-knee socks out of hiding for a bit of a fashion risk. (Unlike Miss Bradshaw, I’m not sure I can pull it off, but I’m going to try!) My feet are perpetually cold, so I went on a thick sock shopping spree last winter and even bought a pair of gray cable knit thigh-highs. They don’t stay up too well at the top, but the slouchy effect just kind of works.
What seems to be in style this season is knee and over-the-knee socks with a short (not plaid) skirt, while keeping the gap between the hem of the skirt and the top of your socks minimal to avoid looking like a hooker. (The Armani photos here show a little more leg, but the look is still very successful.) Also, keep in mind that your socks should be a tight fit—you don’t want awkward bunching in your shoes.
Speaking of shoes, the best style for this look is chunky, low platform heels. Flats are also an option, but I favor heels—as long as they aren’t stilettos. Don’t forget to stick to solid, muted colors or simple patterns—nothing too bold or you’ll end up looking like you’re back in grade school…or like Rainbow Brite.

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