The chukka is one of those boots that never really goes out of fashion because it never really tried to be fashionable in the first place. Two or three eyelets, a clean silhouette, and enough versatility to sit comfortably between smart and casual without looking confused in either direction. The problem is that the market is full of versions that look the part in a product shot and fall apart within a season. Cheap suede that pills, soles that separate, construction that gives up long before the boot owes you anything. We have been looking specifically at chukkas built to last, with Goodyear welted or cement construction worth trusting, leathers and suedes that age well rather than just age, and lasts that work with both tailoring and denim. The heel height matters too. Get it wrong and the whole thing looks clumsy. These are the chukkas we would actually wear into the ground, and then probably resole.