The Most Comfortable Walking Boots
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
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
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
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
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
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
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
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
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
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
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
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
The Most Comfortable Walking Boots
From weatherproof hikers to heeled booties, these comfy boots are made for walkin’.
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