I love ankle boots since they're easier to slip on than calf-length shoes, but still provide more coverage than a mini boot. This one has a curved shaft that's super easy to put on. Plus the cresent pattern across the ankle is an adorable touch.

Leave it to Doechii to style Uggs seamlessly into an otherwise preppy outfit. The rapper wore her Twin Seam New Heights Boots with an of-the-moment bubble skirt, V-neck sweater, and button-down shirt. The combo is unexpected but undeniably cool.