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If building an outfit was like making a sandwich, comfortable clogs would be something like horseradish. Neither is the most elegant of ingredients, but both add a certain structure—and zip—to the equation. In the canon of footwear, clogs are a quirky classic with a history nearly as long as the existence of shoes themselves (the wood-soled kicks have been used for everything from farming to theater, and modern versions nod to the Dutch klompen and Swedish träskor).
In fashion, the clog has transformed itself to become a perfect candidate for the wrong shoe theory, a hack that stylist Allison Bornstein has used to explain how unexpected footwear choices can be the special sauce to any outfit.
Brands, too, have taken to the trend. When Hermès debuted its own clog (a simple wood-soled mule with nailhead trim) a few years ago, it became a cult shoe—and it still commands hefty resale prices while fans wait for the fashion house to bring it back. At Chloé, newly installed creative director Chemena Kamali is resurrecting the boho-luxe vibe one wood-soled shoe at a time: First, with a wedge sandal that all of the front row wore to her Paris Fashion Week debut; now, as a heeled clog that the designer herself has been seen wearing.
One clear winner in the comfortable clogs category is the Birkenstock Boston. The close-toed mule combines a clog’s signature roomy, bulbous shape with the molded footbed comfort of orthopedic footwear to create a cult classic.
But it isn’t just orthopedic footbeds that make clogs doctor-approved. While a molded insole is a key detail that professionals look for in healthy footwear, even a wood-soled clog can be a good option. “A wood or wood-like rigid sole can be excellent because of its intrinsic structure, creating a topographic map for your foot,” says Dr. David Levine, a foot and ankle surgeon at the Hospital for Special Surgery in New York. “Many clogs have a heel or a thickness in the back. That little elevation can help to relax the calf muscles.”
Below is a lineup of the most comfortable clogs on the market—all chosen based on a combination of comfort, cushioning, structure, durability, balance, buzz, and, of course, style.

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