3 boot styles that will get you through the winter

’Tis the season for your low-cut footwear to rest and recover while you break out your boot collection. If you’re rebuilding your rotation or buying your first pair of boots, however, you might be wondering which styles to buy. Here is our guide to three important varieties to break out this month as we hunker down for the impending winter weather.

Chelsea boots

Chelsea boots began life in England during the mid-19th century and didn’t stray far from home until recently. The elasticized wonders were a staple of the mid-’60s mod scene and protected the feet of seemingly every British invader from John to Ringo. Nowadays, they’ve seen a revival on many of menswear’s best dressed. The silhouette is very slim and features elastic side panels and heel pull-tabs. The Chelsea’s close cousin, the ankle boot, has a similar silhouette but uses zippers or straps instead of elastic to ensure a secure fit that many guys—from businessmen to rock stars—will appreciate.

Chukka boots

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. They lace up just above the ankle and traditionally feature a soft crepe sole.

Dress boot

The wingtip dress boot, whose brogued details bring a touch of formal embellishment to casual footwear, is dressed up enough to be worn with a suit and laid back enough to end up under denim or a pair of cords. But they’re not a mullet shoe: they’ve been around long enough to look equally good in either context.