About as casual as all-leather boots get, the chukka (or desert) boot was first worn by British soldiers in Africa during World War II. Afterward, they made their way across the Atlantic, becoming a casual staple for the second half of the 20th century and still gracing the feet of stylish men in the cooler months. Clarks made the originals, but upmarket offerings only improved on the formula.
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What Is a Chukka Boot?
Typically, Chukka boots lace up just above the ankle and feature a soft crepe sole. Modern renditions might replace laces with monk straps, soft soles with Goodyear welted ones or pliable uppers with durable roughout leather. No matter the makeup, they remain a reliable style for milder weather. Of course, Clarks' venerable Desert Boot is a category-defining rendition, but there are loads more you can choose from. The only real prerequisites are the height of the boot (ankle height only) and the number of eyelets (2-5).
How to Wear Chukka Boots
Chukka boots, just as almost all boots do, look best with longer pants, not shorts or cropped chinos. They're also on the more casual end of the boot spectrum, especially if your chosen chukka has a crepe sole. Try wearing yours with a sweater or an overshirt. An Oxford shirt, chinos and Chukka boots are a classic combination, but you can also substitute the Oxford for a hoodie or a flannel.
Avoid wearing your suede or leather chukkas with synthetic fabrics, like super-stretchy chinos or golf polos. The contrast is too obvious. If you must or are forced to wear clothes like this, whether because it's your uniform or it's simply too hot for traditional formal attire, try an all-white leather sneaker instead. Chukka boots are for better outfits.