Women The Toasty Chelsea Boot Dark Coffee Madewell Boots

Lined in faux shearling, this pull-on Chelsea boot feels like a slipper, but with a water-resistant suede upper and chunky weather-sealed soles, it's made to handle snow and slush (confirmed by our designer who tested them all last winter). Plus, cushiness alert: Our MWL Cloudlift Lite padding feels like walking on a…well, you know.