Dear Lucky: How Do I Pull Off Socks With Heels Without Looking Like A Schlump?

Executive Beauty Director

Tommy Ton/Trunk Archive

Socks and sandals take Paris.

Q: I’m intrigued by the whole wearing-socks-with-heels trend—but also terrified. How do I pull it off without looking like a schlump? —Carol

A: Dear Carol, From the glamorous shoes-and-socks at Chanel to the midcalf black nylons with pointy black pumps at Rodarte, this is what a trend should be: fun, fun, fun. You’re not going to be wearing it at your next job interview—so relax and enjoy! And it’s easier than it looks.

I was sitting next to The Man Repeller—a.k.a. Leandra Medine—at the Rodarte show. I looked down; she had on short, white frill-edged socks, like what a six-year-old might reserve for a piano recital, with shiny black loafers. I had to inquire. “Well,” she said, “I wore them mostly because it’s cold, but also because doily socks are silly.” She elaborated: “I like ankle socks with loafers and cropped jeans, or with strappy shoes and a short skirt. I find socks very functional, which is chiefly why I wear them. I also appreciate that sometimes they make me look like I am wearing boots.” It is indeed helpful to think of the sock-shoe combination that way: Whatever you’d wear with boots of that height—skirts (any length), cropped pants (thin or wide), shorts—should work, proportion-wise.

A caveat from Lucky executive fashion director Alexis Bryan Morgan: “Only nice shoes! Don’t combine the sock thing with the sneaker thing.” Alexis’ favorite socks are also mine—Falke. They are expensive ($80 for perfect thick cashmere oatmeal socks), but somehow, they are sexy. “They are! They’re sexy!” she said, laughing. The Falkes are good with a thick-strapped sandal, but wedging one into a pointy pump does not work. Pumps or any sort of spindly heel or strap is where you deploy the 49-cent drugstore black nylons à la Rodarte, or the not-necessarily-man-repellent piano-recital specials.

Naomi Shon

The Man Repeller (Leandra Medine) in frilly, “silly” socks.
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