These boots were made for walking…like, a lot

September 05, 2019 at 05:35PM by CWC

You’ll find plenty of shoes and sneakers you can wear all day without getting any number of miscellaneous body aches. But comfortable boots (that aren’t unintentionally hideous) are hard to come by. Such practical shoe unicorns do exist, however, if you’re willing to do a little legwork.


Wondering how to spot a pair? There a few features to keep in mind while shopping for comfortable boots, according to Miguel Cunha, DPM, founder of Gotham Footcare. The first is shock absorption. Some products and brands will let you know whether their boot has this feature. If not, look for things like rubber soles and try bending the shoe—if it bends in the middle of the sole, this mean it doesn’t have shock absorption and is generally not great for foot support, he says.

Despite what you may think, flat boots aren’t ideal for your foot health. Not in the slightest. “I recommend avoiding boots that are completely flat. They will contribute to pronation and collapse of the arch, which may contribute to planter and posterior heel pain, shin splints, knee pain, and back pain,” explains Dr. Cunha. I’m definitely not interested in dealing with this combination of problems.

Something else to keep in mind, according to Marion Parke, DPM, a podiatrist-turned-shoe-designer, is that “our feet tend to swell throughout the day and you want to provide some room for that. When it comes to shoes, millimeters count.” To factor this into your footwear purchase, she recommends trying on shoes at the end of the day because your boots are one place where flexibility is not a winning trait. (You’re not wearing them to yoga, after all.) Instead, she says to go for structure and support. In other words, look for boots that lift you up and hold you down at the same time.

8 of the most comfortable boots to complete your outfit

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1. Cole Haan Grand Ambition Bootie, $220

This classic bootie comes in black, tan, cheetah print, and gray. And after trying one on, you’ll want all four. The shoe has a molded footbed that provides extra comfort, as well as a lightweight EVA foam outsole that gives you all the cushioning you’ll ever need. There’s no need to break in these babies—they’re cozy from the start.

2. Modern Vice The Original Bolt, $598

While leather makes for a very durable shoe, oftentimes the tradeoff is a level of stiffness that requires continued wear to break in the boots. For their original and cult-favorite style, Modern Vice uses leather that’s already soft and malleable, saving your soles from the painful process. Fans of the boot also rave about how soft and deceptively comfortable the footbed is in particular.

3. Blundstone Super 550, $205

As one of the most iconic boot brands in the United States, Blundstone’s reputation precedes itself. This “super” version of their classic 550 style is an amplification of all good things. The leather is more supple, the boots are lightweight, and they have especially designed footbeds with stronger shock absorption.


4. Marion Parke Tatum Boot, $625

Created by the former podiatrist, these boots were created for optimal foot health and comfort. The material on the Tatum boot is a stretch suede, meaning you won’t have an issue with them being too restrictive on the ankle. They also have arch support and a contoured insole that ensures stability, even with a baby block heel.

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5. Dr. Martens Sinclair Smooth, $185

Generally speaking, I swear by any and all Dr. Martens to support my heavy gait and wide flat feet. These boots specifically changed my life last winter. The sole is extremely thick and padded, which is great when you need a ton of support and have no arch. It also has both a zipper and laces, making it easy to control the tightness.

6. T.U.K. Casbah Boot, $109

This British brand famed for its creepers makes most of its shoes unisex. This means that people who struggle with wide or flat feet (it me!) can find physical comfort and solace in the brand’s offerings. This particular model has the double whammy of laces and a zipper, and it comes with removable comfort insoles.

7. Vionic Mara Boot, $100

Any shoe or boot you purchase from Vionic should do the job when it comes to comfort and foot health. Every pair made by the brand has biomechanical technology concealed within, which supports heal stability and curve comfort.

8. Everlane Day Boot, $225

Everlane says this shoe wins the people’s choice award for their most comfortable boot style. With wear, the leather molds to each individual’s foot, and the combination of the heel thickness and height is meant to make this an extremely walkable and versatile shoe.

Originally published February 20, 2019; updated September 5, 2019.

If you’re going to invest in socks to wear with your boots (yes, even the shearling lined ones) look for a pair from Japan. Trust me. 

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Author Tamim Alnuweiri | Well and Good
Selected by CWC