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Popularized in the mid-20th century, Chukkas continue their long reign of cool. You'll most often find this kind of ankle boot in supple, unstructured leather or suede, with a short run of laces; variations might include a zipper here or there or a crepe rubber sole, as in the desert boot. However they're styled, casual sophistication is assured. (If you can scoop them up on sale, all the better—this is a fashion investment proven to pay long-term dividends.)

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