14 Deceptively Chic Boots That Are Also Weatherproof

When the weather turns less than desirable, your boots have to be ready to take a beating from snow, sleet, rain, and sub-zero temperatures. To guarantee your socks stay warm and dry, you have to look for a waterproof boot, like these from Vivaia. The PU lining ensures that no moisture soaks its way through seams or near the sole of the shoe, keeping you comfortable no matter the forecast.

We've said it close to a million times, but this is by far one of our favorite boots out there. Reviewers agree, some highlighting how "sexy" they look for a chunky boot, while others rave about how easy they are to clean. Made from water-resistant leather, these Chelsea boots have a slight heel to give you some height, and for only $50, they're an absolute steal.

Sure, you don't want to go hiking in these babies, but you'll look amazing wherever you're headed in these surprisingly weatherproof boots. Inspired by boots of the 1970s (everything old is, in fact, new again), the knee-high silhouette isn't only trendy, but will keep your legs nice and toasty when you're wearing dresses or skirts in cold temps.

KCM commerce editor Katie P. swears by these boots for just about everything. From rainy walks with her dog to dinner out with friends, the waterproof leather offers protection, and the elastic sides and back tab make them easy to slide on and off (once they're worn in). This higher shaft ensures your ankles are protected from cold winds and puddle splashes. Her hack for making them extra cozy? Swap the insoles that come standard in them for a pair of shearling ones, which you can get online for about $20.

Before you take these out for a spin in the snow or rain, be sure to coat them with some waterproofing spray so the suede doesn't get damaged (we love this one). But if it's just the cold you're trying to beat, the thick shearling material UGG is known for will keep you cozy.

Dressing the snow bunny part doesn't require owning a ski chalet, but it does call for a stylish pair of boots you can wear while drinking hot toddies in the lodge. Waterproof leather and faux shearling protect your feet from the cold and precipitation, and the contour cushion insole delivers ultimate comfort. And with a heavy-duty lugged sole, black ice will be scared of you. 

If you live in an arctic tundra (or are visiting one!) we recommend this pick from Bos. & Co. Coming up almost to your knees, these shoes are built to keep feet dry no matter the conditions, but aren't as off-putting as a pair of regular snow boots. One reviewer said she felt incredibly steady on icy Chicago sidewalks while wearing these, and that they're extremely worth the higher price tag for how comfortable and sturdy they are.

If aprés ski were a boot, it would be this one. An elongated square toe gives the classic Chelsea a chic upgrade, and the shearling accents ensure warmth and personality. The soles are also lined with faux shearling to ensure your toes are warm even in the most intense winter cyclones.

If bad weather has a habit of ruining your plans, these boots will put a stop to that immediately. Waterproof leather and a tough nylon upper ensure that rain, sleet, snow, and slush have zero chance of reaching your feet or legs. The bungee closure at the top seals things in, while the side zipper makes getting in and out easy. Comfortable underfoot and built to take a beating, these knee-high boots are the kind you reach for when the forecast looks questionable. Plus, Hunter is one of Katie's go-to brands for rainboots, so you know the quality is there.

Hiking shoes aren't only for the trails — they're amazing in nasty weather, too. These ones by our favorite brand, Hoka, have incredible traction and navigate slick sidewalks or muddy yards with ease. Plus, they're entirely waterproof thanks to the GORE-TEX lining, so say goodbye to swampy toes and wet socks.

Thankfully, traditional snow boots have gotten a lot cuter over the years — without sacrificing function. This lightweight boot is like a puffer jacket for your feet. It's insulated to keep your toes and ankles toasty, has a non-slip sole, and can easily be thrown on and off thanks to a zipper.

L.L.Bean's classic Bean Boots never go out of style. This shearling-lined option might be a little pricey, but trust us — they pay for themselves in quality. They have hundreds of five-star reviews, including this one that we couldn't overlook: "I had these expedited to me and they arrived just before the great icing of 2021. I wore them everyday for two weeks straight — especially as I shoveled the snow. I highly recommend these boots for warmth, traction, durability, and good looks." If they can survive that storm of 2021, they're sure to keep you dry during this 2026 one, too.

All of us went through a grunge phase at one point or another, right? Chances are you had a pair of iconic lace-up boots from Dr. Martens back in the day, and now would be the time to pull them out again. If you're in need of a new pair, consider these faux fur-lined Chelseas with a less edgy feel. The leather outer is fully water- and salt-proof, and the soles are designed to grip slick surfaces.

Part-loafer, part-bootie, these chunky shoes do double duty — perfect for winter workdays. Reviewers say they run large, so consider ordering a half-size down to avoid any potential heel blisters. They come in black leather or brown suede, and there's a side zipper for easy access.