It’s that time: From early fall until late spring — and everything in between — is officially winter boot season. No matter what the temperature or precipitation forecast, we always come back to this yearly wardrobe staple, probably because they come in so many different styles for every occasion and can upgrade any look.
But whether you’re trekking through the snow or quickly shimmying to your next location on a cool day, there’s nothing worse than having numb toes, soggy feet or twisted ankles from slipping in lackluster boots. To avoid this, Dr. Bruce Pinker says quality winter boots will stand out from the competition if they “offer moisture-wicking linings, added ankle support, protection of toes, waterproofing, cushioned insoles and adequate traction on the outsole.”
While shopping for a new pair of ideal winter boots you won’t regret adding to your cart, Hammer Tsui, an outdoor enthusiast and travel blogger at A Fun Couple, recommends also keeping these key features in mind:
- Durability: This is a crucial factor because it directly influences the boots’ longevity and performance in harsh winter conditions. Winter boots need to withstand extreme weather, including cold temperatures, snow and ice. Durable materials and construction ensure that the boots can handle repeated exposure to these elements without compromising on functionality. A robust and well-built pair of winter boots stands out by offering reliable protection, maintaining insulation over time and resisting wear and tear.
- Lining or insulation: This cozy feature directly influences the boots’ ability to keep feet warm and comfortable in cold conditions. The lining acts as a barrier against the cold, retaining body heat and preventing it from escaping. Shoppers should look for quality insulating materials like Thinsulate or fleece that effectively trap warmth without adding unnecessary bulk.
- Temperature rating: The temperature rating indicates a pair of boots’ effectiveness in keeping your feet warm in varying degrees of cold. By matching the rating to the expected winter temperatures in your area, you can ensure that the boots provide adequate insulation without overheating or leaving your feet susceptible to cold.
To help find the best options, we spoke to experts including podiatrists, stylists and outdoor adventurers to find out their picks for the best waterproof winter boots, slip-on winter boots, ankle boots and winter riding boots for every lifestyle and activity level. No matter what your personal style is, there’s a pair of boots that’s a perfect match.
Waterproof winter boots
Tsui loves The North Face Chilkat III winter boots — which now come in the Chilkat V iteration — because they seamlessly combine style and functionality. “The waterproof construction is a game changer during wet winter days, keeping my feet dry and comfortable,” she says. “The insulation provides exceptional warmth without sacrificing mobility, making these boots perfect for cold climates.” But the standout feature for her is the TNF Winter Grip outsole, which she says offers superior traction on slippery surfaces. “Whether I'm navigating snowy sidewalks or icy trails, I feel confident in every step,” Tsui adds. “Furthermore, the faux-fur collar adds a touch of style, making these boots a versatile and practical choice for winter adventures.”
These heavy-duty, waterproof leather winter boots come in both men’s and women’s sizes for the perfect fit for any cold-weather adventurer. “Known for quality and long-lasting durability, [these] Doc Martens are a great lace-up option that has slip-resistant technology and an insulated fleece lining for extra warmth,” says Brian Raffio, a former avalanche forecaster and senior adventure travel consultant for Climbing Kilimanjaro.
These L.L. Bean boots are truly a classic according to Raffio, and for good reason. “The L.L.Bean Duck Boot is waterproof, features a steel shank for extra support and comes in an array of sizing for men and women (narrow, regular and wide), making them great for all types of feet,” he explains.
Waterproof boots are a winter essential, and Melissa’s Cotorno boot delivers on both form and function, explains stylist Elizabeth Kosich. “A funky twist on the run-of-the-mill welly, these combat-style, jelly lace-ups have a roomy toe box, soft inner soles and a lug sole built to survive anything,” she says. “Plus, they come in colors galore — 11 to be exact, which includes matte, patent, transparent, iridescent and ombré. The best part? Cleaning them is a dream — one easy wipe down and they’re back to looking like new again.
The Xero Shoes Alpine is a cozy, waterproof winter boot with an insulated polyester fleece lining, a seam-sealed inner bootie and a waterproof membrane. “From a foot-health perspective they have a wide toe box, flexible sole that allows for natural movement and are also very warm and cozy for winter weather,” says Dr. Alissa Kuizinas. “Xero shoes are comfortable while allowing the foot to move efficiently.”
This waterproof boot comes standard with a premium removable orthotic that supports your arch and positions your feet for better weight distribution, explains Derek Roach, owner of Flow Feet Orthopedics. “Designed with a faux-fur collar, this boot has a trendy look while offering support for a variety of foot conditions, including plantar fasciitis, pronation and heel pain,” he says.
The Alps boot is a versatile winter boot that maintains a modern style yet supports and cushions, according to Roach. He also appreciates that it was designed for inclement weather with a gusseted tongue that keeps water out. “The removable premium orthotic anatomically supports your feet from heel to toe,” Roach adds. “There are multiple layers of inserts to adjust the depth to accommodate orthotics, swelling or foot conditions that need more interior space.”
You’ll be a dry-footed style star in these waterproof Chelsea boots, says stylist Christina Stein. “Sam Edelman has amazing waterproof booties that are totally on-trend for this year.”
Slip-on winter boots
Bogs Women’s Classic High Solid Boot offers exceptional performance and comfort during Tsui’s adventures, and she recommends them for the reliable waterproofing that keeps her feet dry in various terrains and climates. “These boots have been a game changer, especially in cold and wet conditions. The easy pull-on handles make them convenient for quick on-and-off situations, which is crucial when navigating through unpredictable weather or exploring diverse landscapes,” she says. “The durable construction and insulation ensure my feet stay warm and comfortable, making the Bogs Classic High Solid Boot a reliable companion for any travel escapade, from urban exploration to off-the-beaten-path adventures.”
According to Kosich, “cool girl” winter clog booties are always a good look. “Add a fuss-free slip-on design and shearling liner and it’s a win-win,” she says. “These are particularly comfy with a stiff leather upper that delivers support and a soft, supple leather shaft that makes them luxury. The platform heel is a nice, manageable lift for all-day wear, and the polyurethane sole softens the wood base, making them quieter.”
Made from suede and a smooth, rubberized leather upper, these flexible Chelsea boots are lined with microfiber and have no heel for a neutral footbed. “These slip-on boots are a great option, super easy to pull on and off with the elastic inserts, with durable soles that are great for winter,” Kuizinas says. “These boots are lightweight; have a flat, flexible sole and a wide toe box; and allow for proper movement of the foot and ankle while walking.”
For boots with a modern feel, Roach recommends this versatile pair with a slip-on feature to wear casually this season. “This boot includes the Vionic Vio-Motion Technology soles, which are flexible, supportive and cushioned,” he says. “The flexible design allows your foot to move more naturally as you walk. The articulated pods provide shock absorption in each step to reduce foot fatigue. It also is designed with a raised arch to support your feet.”
This boot offers ankle stability and a supportive insole, including a stabilizer heel cup that Roach explains is ideal for those who need motion control features in their footwear. “The Drew Walk Right [Technology] inserts help with heel cushioning and stability,” he says. “The Jayla features durable uppers and a quality construction to last you multiple seasons.”
This lightweight slip-on boot adds a little height with a 1.37-inch heel while keeping foot health in mind. “The Vio-Motion Technology supports your arch and stabilizes your feet as you walk, and the flexible sole allows your feet to move naturally to reduce foot discomfort during wear,” Roach says. “The lug sole design makes for better traction for a variety of terrains and weather.”
Winter ankle boots
If you’re looking for winter boots that deliver comfort, weather protection and that extra grip that makes exploring worry-free, Tsui raves about this Columbia option. “My recent travels were a breeze, thanks to the Columbia Women’s Ice Maiden II boots,” explains Tsui. “They’re incredibly comfortable and perfect for long walks or hikes.” But what impressed her most was how well they kept her feet warm and dry, no matter the weather. “The waterproof feature came in handy during unexpected rain, and the insulation was a game changer in colder temperatures,” she adds. “The standout, though, was the traction on the sole; it’s like having built-in stability on any terrain. Whether I was navigating rocky paths or slippery surfaces, these boots provided a secure grip.”
Red Wing has been around since 1905, explains Patrick Burch, owner of Cave + Post Trading Co., making boots proudly in America since the beginning. “They are a true heritage brand with a reputation for quality, fit and style both for work and fashion,” he says. “The Chelsea is comfortable right out of the box and gives a rugged, stylish look to anyone who puts it on. It is a great, all-around slip-on boot that should be in [anyone’s] closet.”
For cool winter days, Kuizinas votes for these ankle boots with a soft fleece lining and three color options. “They also have great features for foot health, including a wide toe box, zero drop and flexible sole,” Kuizinas says.
This winter ankle boot has a dual-zipper feature that Roach says allows for easy entry into the shoe. “Plus, they also have a supportive insole to hug your arches and cushion your heels,” he says. “The insole includes a rigid heel stabilizer to help with those that overpronate. The slip-resistant polyurethane outsole offers better traction on slippery surfaces and varying terrains.”
A bold ankle bootie with soft, supple leather uppers that are gentle on your feet, these boots come with a suede microfiber sock lining for an extra-cozy feel. “These boots feature the signature Tiny Pillows footbed that feels like you’re walking on a cloud,” Roach says. “If you plan to be on your feet for long periods this season, the Ezra will keep you comfortable and supported.”
Winter riding boots and knee-high boots
During Tsui’s winter travels, the TuffRider boots surpassed her expectations. “These boots handled winter conditions surprisingly well, offering a decent shield against the cold and dampness. The elastic gusset along the zipper was a game changer, adapting to various calf sizes for a comfortable fit,” she says. “While they might not boast all the high-end features, their reliability in different terrains and adaptability to winter climates make them a practical choice for outdoor enthusiasts and travelers seeking warmth and comfort on chilly adventures.”
For a riding boot that doesn’t compromise in style with belted detail or fit with a foam insert and rubber traction sole, consider this suede option. “These Clarks knee-high boots are recommended for their quality construction, comfort footbed and added traction on the outsole,” Pinker says.
Available in three different widths and 16-inch calf circumference, these leather buckle riding boots are both size-inclusive and on-trend for the winter. “The Propet [Tasha] Riding Boot offers considerable style, cushioning, outsole traction and a removable insole,” Pinker adds.
“Available in a medium calf (14.96-inch circumference) or wide calf (16.93-inch circumference) is this equestrian-inspired riding boot,” Roach says, “with water-repellent leather uppers and a supportive footbed to help with foot discomfort at the heel and arch areas.”
These over-the-knee heeled boots have it all — style, comfort and drama. “The sleek, minimalist design is the perfect cold-weather boot silhouette, its 2.7-inch heel height gives you an edge but not pain and the thigh-high style guarantees you get noticed,” Kosich says. “The velvety suede is gorgeous, top quality and lasts longer if regularly waterproofed and brushed.”
Despite being a warm, waterproof knee-high boot with a rubber sole, Xero Shoes’ Mika style won’t weigh you down. “They are lightweight, with a wide, anatomical toe box [and] flexible sole and allow for natural movement of the foot,” Kuizinas says. “Plus, they have a zipper for easy on and off, and they are both comfortable and stylish.”