A Search for the Perfect Fall Clog, the Bookworm’s Fashion Shoe

We've rounded up our favorite smart and spiffy pairs of clogs that you'll want to wear all season long.

Transitions are never easy, especially for an avowed member of the church of clog. It’s already too cold for my open-toed summer clogs, yet it won’t be time to break out the cozy fuzz-lined clog boots for a good few months. These last couple of weeks I’ve been trotting around in my Ronald McDonald–esque white Danskos, but as the creator of the #cloglife hashtag and related Instagram account—which celebrate both the clunky footwear and the free-to-be lifestyle that goes with it—I should aim higher than a shoe that invites weary declarations of, “Only you can get away with those.” Not to get too Sheila Heti about it, but what is a fall clog meant to look like anyway?

Unlike the seasonal player whose job is to aerate or insulate, fall clogs don’t have any real utility. Yet this is exactly where the beauty lies. They’re clogs at their most fashion. The perfect fall clog is a mood-setter: spiffy and smart and full of promise, the footwear equivalent of a freshly issued library card. “A fall clog should help you feel like a faux virginal schoolgirl,” says Grace Farris, M.D.—chief of hospital medicine at Mount Sinai West by day, cartoonist by night, and around-the-clock clognoisseur (she tells me her fall #cloglife curriculum includes: the Cecily Brown exhibit at the Gallery Met in Lincoln Center, Liana Finck’s graphic memoir Passing for Human, and “buying a prairie dress”). As for actual clogs, she points to No. 6’s best-selling Old School—in a rich camel and with a high heel that elevates the look in all the right ways.

Masha Popova, Russian Vogue’s web editor and passionate ugly-shoe enthusiast, has been living in her DiorQuake clogs, a black calfskin model with silver studding. “They are the most comfortable wooden clogs,” she says. “I wore them during Paris Fashion Week—and walked over nine miles a day in them.” Dior’s clog offering has snob appeal and the shoes are deceptively streamlined, despite their clunk. It comes in textured versions, as well: an embroidered floral and denim patchwork. “I think a pony-hair clog is the best for fall!” says card-carrying #cloglifer Kat Henning, who happens to work as a designer at No. 6. “It adds a little coziness and looks best when worn with beautiful woolly socks.” The clog-and-sock phenomenon is hard to argue with, and just thinking about it gives me more reason to purchase the piebald pink version I’ve been low-key admiring from U.K. designer Penelope Chilvers. This furry shoe would pair beautifully with a frilly anklet or delicate sparkly Darner sock.

Another clog that ticks the touchy-feely, sock-friendly box is the quilted Lego from Angelina Rennell’s California-based label Beklina—with new colors for gourd season including bloodred and a stunning hunter green. Rachel Comey’s Level is a block-heel platform with a pointed toe and suede finish. Handsome as the shoe is, it’s more geared toward a starchitect than #cloglife, and I’m not sure how it would pair with a chunky pair of socks. So personally, I’m going to spring for a pair of No. 6’s tasseled Keats Kiltie clog with a high heel—not in the funky pony hair, but in a smooth indigo that speaks to my Oxbridge fantasies and bookish tendencies (have I mentioned I have a novel coming out next summer?).

All set. Now I just need to find my status socks.

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