25. The Knee-High Boot — From Alexander Wang to Altuzarra, knee-high boots seemed to be making a comeback, which means it's time to dig yours out of the back of your closet, or go and finally make the splurge. A decent pair shouldn't cost you an arm and a leg, but expect to put down a decent amount of cash if you don't feel like resoling, retooling, and repairing them every six months.

Madewell The Watchtower Boot, $279.99, available at Madewell; Stella McCartney Knee Length Boot, $847, available at Farfetch.