It’s Time to Learn the Most Important Styling Trick You’ll Need This Winter

Welcome to the season where the boot and pant are set up for a long, cold-weather-induced union—and a beautiful but tricky union it is. Or it can be. The problem? Unlike summer, when a sandal acts as the fit-all footwear for any bottom, finding the right pant length to suit a boot takes some practice. Not just any boot will do! From the potential for frosty, naked ankles to awkward chunks marring a silhouette, problems can arise.

The first tip: Think of it like a leggy equation—paying special attention to the balance between the boot and pant is key. A boot-cut jean has a sturdy fit that goes along perfectly with a low-heeled military boot. As for the beloved midi heel? Slim-fit trousers are a stellar pairing, working as leg-elongator. For those chilly days when you are lusting after a cropped culotte but know it will ultimately lead to some chilly shin skin? A knee-high boot can act as an unexpectedly cool cover-up. And remember, funking it up courtesy of a pattern-forward jean and peppy-printed shoe never hurts. Here, the best boot and pant pairings to get you started for winter.