Boot season brings out the best in my style sensibility: cold-weather footwear has staying power that defies the temperatures, and because I’m often wrapped in outerwear, I showcase them as best I can. Knee-height boots have the upper hand this year and it seems everyone’s been tucking their pants directly into said boots.

The trouser-tuck is an advanced maneuver, however, lending itself to some controversy if done incorrectly. The 2019-2020 version includes loose trousers, so if the pants are too tight you miss the style completely; grab too-billowy slacks and you’re dangerously close to looking like a pirate. For a true lesson in tucking pants into boots, we turned to this season’s masters who’ve proven how versatile this trend can be.