When the days get shorter, you know it’s time to switch out your shoes for some new-season boots. Trying to decide between chukkas and Chelseas? Take a closer look at the boot styles we’re tipping for fall, together with some pointers on how to wear them.
Also known as desert boots, chukka boots were originally worn by British soldiers in Egypt in World War II, but they’re still relevant thanks to high-profile fans like Prince Harry. These classic boots are characterized by a slim sole, and have just two to three pairs of eyelets to take them to ankle height. Comfy and casual with a rubber outsole, these are the boots you’ll be living in at the weekend (or, you know, on a royal tour of Africa).
Sleek and streamlined with the telltale elasticated gusset on the side, these casual boots are named after London’s Chelsea neighborhood — the place to hang out back in the Swinging Sixties. Originally invented by Queen Victoria’s shoemaker, Chelsea boots were the footwear of choice for The Beatles, The Rolling Stones, and even the Stormtroopers in Star Wars. Dressier than a sneaker but still casual in feel, the Chelsea boot is the perfect all-rounder.
Get prepped for fall weather with a pair of durable lace-up boots, which sit higher on the ankle and have deep tread soles for traction. Whether you’re planning on shoveling snow or doing nothing more strenuous than the weekend grocery shop, every guy needs some rugged boots in his collection — pair them with denim and a flannel shirt or navy sweater for every day.