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Best Overall: Everlane Square Toe Chelsea Boot at Everlane
"Boasts an elegant look and sturdy construction."
Best Waterproof: Sorel Women's Ainsley Conquest Boot at Amazon
"Keeps your toes warm and dry, no matter how wet it is outside."
Best for Wide Calves: Frye Melissa Belted Tall Boot at Zappos
"The slimming silhouette is flattering on everybody."
Most Comfortable: UGG Classic Cardy Boot at Amazon
"Offers a cushiony, soft fit, with plenty of good traction."
Best for Men: Red Wing Moc Toe Boot at Nordstrom
"A men’s boot that’s just as comfortable as it is fashionable."
Best Tall Boot: Sam Edelman Penny Riding Boot at Nordstrom
"Refined, high-quality, and elegant."
Best Combat Boot: Dr. Martens Pascal Virginia 8-Eye Combat Boot at Nordstrom
"Add edgy, grunge style to your look with these boots."
Best for Women: Bos. & Co. Brave Waterproof Chelsea Boot at Nordstrom
"They're beautiful, durable, and comfortable."
Best for Extreme Cold: Sorel Caribou Boots at Zappos
"The felt inner lining insulates up to -40 degrees."
Best Bootie: Frye Carson Piping Bootie at Zappos
"Crafted from the highest-quality waxed pull-up leather."
Our Top Picks
Best Overall: Everlane Square Toe Chelsea Boot
For a classic, sophisticated boot that never goes out of style, the Everlane Chelsea Boot is the perfect shoe. This beloved boot boasts an elegant look and sturdy construction: a low stacked heel, leather heel tab, elastic panels for easy pull-on, and a chic square toe. Crafted from ultra-soft, supple Italian leather, the Chelsea Boot is available in four warm, attractive shades — Black, Biscuit, Peanut, and Chocolate — that go with virtually everything. Just remember they have a narrow fit, so you’ll want to size up if your foot is wide.
Best Waterproof: Sorel Women's Ainsley Conquest Boot
You’ll look forward to gloomy, rainy days when you have the Sorel Ainsley Conquest Boots in your closet. These chunky, rugged boots are crafted from waterproof full-grain leather with seam-sealed construction, keeping your toes warm and dry, no matter how wet it is outside — but most importantly, you’ll look stylish traipsing around in the rain. The red laces and contrasting black leather-and-suede material make for an eye-catching combination — pair these boots with jeans, skirts, or dresses for a look that’s both functional and chic.
Best for Wide Calves: Frye Melissa Belted Tall Boot
Ladies with wide calves, take note: the Melissa Belted Tall Wide Calf Boots from Frye are simply gorgeous. It fits comfortably around the calf, and the slimming silhouette is flattering on everybody. Like all Frye boots, these are made from buttery-soft, superior-quality leather that will easily last a lifetime. With the heritage Melissa button, inside zipper closure, and belted bridle strap, these boots are classic and easy to wear.
Most Comfortable: UGG Classic Cardy Boot
With the UGG Classic Cardy Boots, you’ll just want to snuggle up next to a crackling fire while camping — toting a good book and a glass of wine in hand. They’re just that cozy. Made from chunky sweater knit, these UGG boots can be worn one of several ways, depending on your mood: you can slouch the material down around your ankles, pull it all the way up, or fold it over for a shorter style. Lined with a plush wool insole, the Cardy boot offers a cushiony, soft fit, with plenty of good traction.
Best for Men: Red Wing Moc Toe Boot
For a men’s boot that’s just as comfortable as it is fashionable, the Red Wing Moc Toe Boots are a fantastic pick. They offer optimal support and protection from the elements (they’re both water- and scuff-resistant), and their rugged construction makes them the perfect statement piece to incorporate into your wardrobe, especially in time for winter. The supple, high-quality leather conforms naturally to the shape of the foot, which results in an extremely cozy fit, and the lace-up style adds sophistication to any outfit. The Moc Toe Boots come in two colors: Concrete Leather and Copper Brown.
Best Tall Boot: Sam Edelman Penny Riding Boot
Channel equestrian style with these classic boots. The Sam Edelman Penny Leather Riding Boots look good on just about everyone, thanks to the shoe’s stylish silhouette and rounded toe. Plus, the pull-on tab and back-zipper closure make for easy wearing. Refined, high-quality, and elegant, the Penny boot can be dressed up or down: pair them with jeans or bare legs for a casual outfit, or a tailored dress or skirt for a look that’s professional yet glamorous.
Best Combat Boot: Dr. Martens Pascal Virginia 8-Eye Combat Boot
Practical and utilitarian, the Dr. Martens Pascal Combat Boots are a 90s-era shoe classic. Add edgy, grunge style to your look with these boots — they’re crafted from soft, fine-grain Nappa leather that doesn’t need to be worn in, and finished with functional details like a cushioned Goodyear-welted rubber sole and woven back pull tab, so you can slip them on and off with ease. Cut just above the ankle, with a trendy lace-up silhouette, these boots look great with tapered pants, printed skirts, floral dresses, and really anything else you want to pair them with.
Best for Women: Bos. & Co. Brave Waterproof Chelsea Boot
There’s nothing like a classic Chelsea boot, and these Chelsea boots from Bos. & Co. are beautiful, durable, and comfortable. Made from plush Suapel soft-touch lining, these boots offer cloud-like comfort and excellent traction, and the Tan/Rust Suede color is sleek and cool. And, as an added bonus, they come equipped with a breathable, water-repellent membrane so your feet stay dry and toasty even in the crummiest, rainiest weather.
Best for Extreme Cold: Sorel Caribou Boots
When the below-freezing temperatures hit, be sure you have a pair of Sorel’s Caribou Boots on hand. These comfortable boots keep your feet warm and dry, and they feature a waterproof outer shell and rubber sole that guarantees sturdy comfort, even in the iciest conditions. The removable ThermoPlus felt inner lining insulates up to -40 degrees and provides an extra layer of cushioning, so you’ll be able to walk in them for hours without getting cold feet.
Best Bootie: Frye Carson Piping Bootie
Getting your first pair of Frye boots is a veritable rite of passage — and the Carson Piping Bootie is truly one of the brand’s coolest shoes. This modern interpretation of the classic Western boot is crafted from the highest-quality waxed pull-up leather and features a signature piping detail. And, the leather is so soft and well-made, you’ll feel like you’ve worn these boots for years, even from when you first try them on.