Kendall Jenner successfully pulled off this season’s most intimidating boot trend, but that doesn’t mean this maneuver comes easy for the average fashion girl. Don’t stress—with the right pairings and a little confidence, super-tall, OTK boots can be worked into your fall wardrobe with ease. Make like Kendall by teaming a thigh-high pair with a chic khaki minidress, classic leather jacket and delicate gold jewelry. Now that’s an effortlessly cool look fit for the season ahead.