Blundstone 558 Boots
A favorite of everyone from ranchers to city slickers, these time-honored boots are cute enough to post online, but durable enough to survive rain, snow, and yard work. Better yet, they boast shock-absorbing outsoles and removable footbeds, meaning you can add your own orthotics. Saylee Tulpule, D.P.M., a podiatrist with Foot and Ankle Specialists of the Mid-Atlantic in Maryland,
likes them for their “cushion, pulls tabs for easy slip-on, and casual feel,” mentioning that they’re great for all-day walking. At just under $200, they’re certainly an investment, but one that you can trust will survive many colder seasons to come. One Zappos customer writes “My first pair of Blundstones lasted 10 years. I imagine these will last that long, too.”
Dr. Scholl’s Rate Ankle Boot
These perforated suede ankle boots look at least double their price, and they come loaded with the brand’s signature cushioning and a pull tab for easy wear. Plus, reviewers love how easy they are to style with cold-weather outfits. “The insole is amazing, it forms to your feet which feels great and makes it so there’s really no break in time for them and were comfortable from the jump!,” one reviewer says. They even come in wide sizes, although wearers warn that they are narrower than one might expect.