Vionic Kamryn Boots
Whether you’re hitting a meeting or happy hour, these sleek, understated ankle boots are exactly what you need to complete your look. Beyond their aesthetics, though, there’s plenty else to love, including a 1.59-inch heel, hidden arch support, and a removable footbed, which are great for all-day wear, Dr. Tulpule notes. You can choose among four colorways, but classic black is always a safe (and chic) option. One Zappos reviewer says “these are my go-to footwear if I was going to do a lot of walking and did not want to have any foot problems.”
Munro Neko
Dr. Tulpule herself has issues with plantar fasciitis, and she says these boots get her through fall and winter with zero issues, thanks to their removable insoles, short-but-stylish heels, and zip closures. For extra support, slip in your own orthotics—you’ll actually be able to walk around comfortably. One happy Zappos customer adds that “Munro has a generous toe box, so your toes won’t feel pinched.”