Why we love them: This cool-girl boot is nothing new to the shoe scene, but this season's version of the Chelsea boot heralds its second coming. Decidedly more brazen in its structuring, color combinations, heel heights, and finishes (hello, brogue!), welcome to the world of Chelsea Boot 2.0.
How to wear them: Our favorite way to wear the Chelsea boot? With a pair of ankle-cut skinny jeans, scrunched-down socks, knitted layers and a lightweight jacket on top.