Dr. Scholl’s Shoes Laurel Ankle Bootie Boot
This new-school take on the classic Chelsea boot is just begging to be worn this fall. Available in an assortment of leather and suede neutral colors (all featuring a stacked, contrasting heel), they’re guaranteed to be in constant rotation. Dr. Tulpule appreciates the super-stable 2-inch heel, which is just high enough to make a statement, but not too high to be comfy, and Dr. Bhuta notes that the side stretch makes it easy to slip insoles in. One Amazon customer says “You can wear these walking around like a comfortable tennis shoe they are so comfy!”
Red Wing Heritage 6″ Classic Moc Boots
When you can’t compromise performance (or style), Red Wings should be your go-tos. First introduced in 1952, this style has since been updated with soft, water-resistant leather, lightweight outsoles, and cushy insoles. Your boots can even be resoled, meaning they’ll last as long as you’re willing to keep them. The only drawback, reviewers say, is that they take a while to break in. Sure, they’re an investment, but one that you can trust. One Zappos customer says “These are the best and most comfortable work boots ever!”