When it comes to shopping for footwear, we tend to look for just two things: are they cute and are they comfy. But winter boots are a whole other ball game. We know they should be warm and come with plenty of traction to combat icy sidewalks, but what else should we be looking for in a solid winter boot? We asked three podiatrists— Dr. Miguel Cunha, a board-certified podiatric surgeon and founder of Gotham Footcare in NYC, Dr. Sarah Haller, DPM, of Essex Union Podiatry, and Dr. Jaqueline Sutera, DPM, a Vionic Innovation Lab member—to share their recommendations on what makes any particular style worth buying, along with a few specific picks to shop ahead of the season’s first snow.