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-high 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 proved how versatile this trend can be.
