The Most Comfortable Walking Boots

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Courtesy of Retailer

As anyone who's walked a mile in boots knows, there's a difference between a pair that feels comfortable when you initially put it on and one that feels supportive after hours on your feet. In pursuit of the latter, Travel + Leisure spoke with Jacqueline Sutera, DPM, a spokesperson for the American Podiatric Medical Association and a member of Vionic’s Innovation Lab, where she advises the comfort shoe brand on the biomechanics of the foot as it works to develop health-conscious footwear.

Though, according to Dr. Sutera, a walking boot's comfort is not so much about the brand or the style, it's about the way it's built. There are three design components you want to look for: shock absorption, cushioning, and arch support.

The first, shock absorption, protects your joints and the natural padding in your heel each time your foot strikes a surface. In most cases, it comes from the construction of the shoe’s outsole. With boots, it's smart to look for a thicker sole that’s sturdy and structured.

“You want to stay away from really flimsy — I call them ‘buttery’ — super flexible and mushy boots like the traditional Uggs,” Dr. Sutera said. “They’re pretty bad, especially for people that have flat feet and especially when they’re worn out. After one season, unfortunately, Uggs are just made of such soft material that it wears away and you can hurt yourself by walking around in shoes that are old and worn, when the sole is deformed.”

If you pick up a boot and you can totally bend the sole, it’s too flexible and won’t give you enough support. It might feel comfortable when you step in, because it’s “squishy,” but that doesn’t mean it’s necessarily good for you, Dr. Sutera advised. She does think there are some newer Ugg styles that are getting better, with a higher-quality sole and a bit of a stacked heel.

"If you’re really partial to that brand, don’t go for the traditional pair," she said. "Look for the newer style that has a thicker sole that’s a little more sturdy and you can add an insert."

The next two key components, cushioning and arch support, both come down to the boot's insole. Several brands, Vionic included, already have arch support built in; though if a boot you like does not, Dr. Sutera recommends swapping out the manufacturer's insole for an insert. Choosing one can be a bit intimidating, so she broke them into three categories: basic drugstore brands, those sold at running shops, and the custom orthotics you can get at the doctor's office.

"In the middle category, Spenco and Superfeet are probably my favorite," Dr. Sutera said. "They’re a higher quality than the drugstore brands, but what they’re missing is the ability to give you a prescription. So for people that have one foot that’s larger than the other or a bunion on one side or extremely flat feet, there are a lot of different customizations we can make at the doctor’s office."

As for upper materials, Dr. Sutera suggested looking for leather boots because the material is soft yet very durable. But she cautioned against certain suedes because if they're too flimsy the upper won't add any structure to the boot.

Once you've got your new comfy boots, you may not want to wear them right away. Dr. Sutera warned that you can actually damage your feet by using them to break in a shoe that’s too stiff. She recommends taking them to your local shoemaker or using a wooden shoe-tree. For a DIY version, she also mentioned using a baseball or a softball to stretch the material, depending on how big the shoe is.

With Dr. Sutera's tips in mind, we found 12 pairs of comfortable boots that set your feet up for a day of exploring in style.

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Each product we feature has been independently selected and reviewed by our editorial team. If you make a purchase using the links included, we may earn commission.

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Simple (but Smart!) Heeled Booties

Courtesy of Zappos

Canadian footwear company Blondo’s waterproof "Villa" boots have become a crowd-favorite for their cushioned footbed, durable rubber outsoles, and sleek style. The fully seam-sealed uppers come in seven shades of leather or suede and are resistant not just to water, but also to staining from salt on the street during winter.

To buy: zappos.com, $150

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Buckled-up Ankle Boots

Courtesy of Vionic

Dr. Sutera's recommended brand, Vionic, makes this edgy pair that will look just as good with denim as it will with a floral midi dress. It's got a sturdy, stacked heel that’s 3 inches tall for a flattering, yet still manageable amount of lift. Plus, the leather uppers are already weather-resistant, so you won't need to treat them before wearing.

To buy: vionicshoes.com, $180

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Timeless Riding Boots

Courtesy of Amazon

If you’re a fan of Kate Middleton’s travel style, a pair of riding boots is a must in your footwear lineup for fall and winter trips. This brown leather pair by Sam Edelman has a stacked, 1.25-inch heel and a full-length zipper to make it easy to get them on and off.

To buy: amazon.com, from $66

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White Ankle Boots

Courtesy of Everlane

Just like Everlane's best-selling Day heels and flats, the brand's new Day boot is designed to fit like a glove. The buttery soft leather will mold to your feet when you start wearing them every day (like we plan on doing). It's available in four more colors, but we love how bold this bright white is.

To buy: everlane.com, $225

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Classic Chelsea Boots

Courtesy of Nordstrom

Clarks has been counted on to make comfy shoes for almost 200 years, and the brand’s boots are no exception. The “Clarkdale Arlo” boot is made of smooth, strutctured suede and stretchy textile while the footbed boasts a plush, removable insole.

To buy: nordstrom.com, $160

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Vintage-inspired Hiking Boots

Courtesy of Zappos

Trusted hiking-shoe brand Merrell really delivered with the waterproof “Sugarbush” boot. With a padded tongue and collar, air cushioning in the heel, and an insulation that lets moisture out but not in, they’re ideal for a full day of adventure.

To buy: zappos.com, $220

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Waterproof Boots That Feel Like Slippers

Courtesy of Nordstrom

As Dr. Sutera suggested, you'll want to lean toward Ugg's newer, sturdier models, like the “Kesey” boot. The leather and wool-blend upper are fully waterproof and they have a grippy rubber outsole, but the supportive interior — which is lined with the brand’s signature cozy wool lining — is by far the best part.

To buy: nordstrom.com, $160

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Over-the-knee Boots

Courtesy of Zappos

Stuart Weitzman’s 5050 boots are a cult-favorite in the over-the-knee category, with their glovelike fit and cushioned soles. They’re available in narrow, medium, and wide (yes, big enough for athletic calves) sizing and a variety of leather and suede uppers.

To buy: zappos.com, $695

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Stylish Leather Lace-ups

Courtesy of Zappos

Timberland's “Sutherland Bay” boot will look just as at home in the urban jungle as it would on the trail. The upper is treated with a stain-blocker and the antimicrobial OrthoLite comfort foam insoles provide ample support from dawn to dusk.

To buy: zappos.com, $145

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Sleek Block Heels With Comfort Technology

Courtesy of Nordstrom

You'd never guess it by looking at them, but Rockport has worked its proprietary truTECH comfort system into this sleek pair of pointed-toe, leather ankle boots. The heel is engineered to absorb shock and the insole is constructed with anatomically cushioned retention-foam to provide support where you need it most.

To buy: nordstrom.com, $170

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Modern Western Booties

Courtesy of Zappos

Heading out west? You’ll want to pack Frye’s “Billy Shootie” with its cut-off cowboy boot sillhouette, smooth leather, and easy-pull heel tabs. Inside, it's got a broken-in feel to match the look, letting you take on places like the adobe town of Taos, New Mexico atop a soft leather lining and a cushioned footbed.

To buy: zappos.com, $298

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Heeled Booties With a Metallic Touch

Courtesy of Amazon

One of Travel + Leisure's editors reported this pointed-toe pair by Franco Sarto is “super comfy for how they look.” We love the gold detailing on the 1 1/4–inch heel and the pull-tab on the back to make on-and-off easy. They’re also available in slate gray, black, and leopard print.

To buy: amazon.com, from $32

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The Most Comfortable Walking Boots, According to a Podiatrist