L.L.Bean Bean Boots
You’ve probably owned a pair of these at some point, and for good reason: They’re a classic with some impressive specs. Built with grippy soles, sturdy stitching, and weatherproof leather, they’re ideal for those gray days that start around October. “They’re perfect for those cold, wintry months,” Dr. Tulpule says, and they even come with extra room for warm socks. One happy Zappos reviewer writes “I was extremely happy as the fit was perfect and they are extremely comfortable to wear all day long (even at my job where I am on my feet for 6+ hours).”
Salomon X Ultra 4 Mid GTX
These hiking boots have a high-tech charm to them—they’ll look great on the trail and on city streets alike. Dr. Tulpule especially appreciates the fact that they’re waterproof, thanks to a trusty GORE-TEX outer, meaning they’ll survive the slush in your future. And on top of all that, their rugged outsoles are designed to make tough descents as safe as possible. Bonus? These are orthotic friendly! One Zappos customer says “Even with my orthotics, they still fit great and allowed room for my toes to spread in the toe box.”