The 15 Most Comfortable Boots to Wear All Day, Every Day This Fall

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As a New York resident who is constantly trekking through city streets and climbing steep subway stairs, I’ve learned to maintain a reliable rotation of comfortable walking shoesin my closet. Now that autumn has officially arrived, the pressure is on to find the most comfortable boots that will carry me through this season and beyond.

While scouring online retailers and brands for leather boots that are worth the investment, I’ve realized that prioritizing comfort requires careful consideration. For one, you’ll want to make sure that the inner lining of your boot is made from a quality material that is equally soft and durable, like natural leather. You’ll also want to be wary of extremely high heels, which tend to place pressure on the ball of your foot.

Marion Parke, podiatric surgeon and luxury footwear designer, tells Bazaar that shoppers should also look for supportive soles, especially if they are shopping for boots to wear during the colder months. “On those days when the weather can be wet, salty, or icy, it's best to wear boots that have either a full rubber sole or a rubber injected area under the forefoot for traction and safety,” she explains. Parke also notes that those with high arches should think about selecting a pair of boots with a zipper closure: “[P]utting on and taking off a boot, especially a tall boot, can be a struggle with high arches,” she explained.

In addition to considering the factors above, I’ve researched street style trends across the globe to inform the following list of the most comfortable boots. Ahead, you’ll notice pointed boots, wide-calf boots, and biker boots, which appeared everywhere during New York Fashion Week and Milan Fashion Week. And of course, you’ll recognize other timeless—and comfortable—styles like Chelsea boots and knee-high boots.

Catherine 70 Boot

Feel free to walk all day long in these Catherine 70 boots, because Marion Parke's collection is heavily influenced by her expertise as a podiatric surgeon. Each shoe is equipped with a supportive insole that relieves pressure on the foot.

Sizes: 35-42 (5-10)

Colors: Brown, black, grey

Heel Height: 2.8"

Flin Knee-High Boot

Perhaps one of the most versatile boot styles of all is the classic black boot. With an uncomplicated silhouette, these Dolce Vita boots can easily match with a luxe satin slip dress and a structured blazer or a pair of jeans and a knit sweater. Not to mention, they're lined with breathable linen and the interior is detailed with elastic to offer more movement in the calf area.

Sizes: 5-12

Colors: Black (leather), black (suede), ivory, brown, multi-colored

Heel Height: 3"

What reviewers are saying: "The real benefit is the perfect heal, toe combo. The toe is just wide enough to accommodate my foot issue without looking frumpy and the heel is in the sweet spot of being high enough to still be stylish but low enough to be comfortable."

Yuliana Boots 60mm

Slip into these pull-on boots with ease, as there's no need to fiddle around with a zipper. Stuart Weitzman's Yuliana Boots also feature a block heel, which yields ample stability and support in comparison to stilettos.

Sizes: 5-11

Colors: Cream

Heel Height: 2.25"

Maryana Block Pointed Toe Knee-High Boot

Each year when fall rolls around, I like to take my cherished croc-embossed boots out for a spin. Whether I'm walking to my favorite coffee shop, which is 25 minutes away from my apartment, or I'm spending an entire night out on the town, I can count on these sumptuous boots to get me through without any discomfort.

Sizes: 5-11

Colors: Dark brown (croco), black, cream, snake print, black snake embossed

Heel Height: 3 1/4"

What reviewers are saying: “I love these boots so much I never went to take them off. So comfy and so stylish.”

Embroidered Two-Tone Leather Cowboy Boots

Ganni's cowboy boots are Western-inspired works of art. Adorned with geometric embroidery and intricate stitching, these boots will capture the attention of any aesthete. And as for comfort, the low heel will make you feel like you're practically wearing flats.

Sizes: 36-41 (6-9.5)

Colors: Black/ brown, black/ cream

Heel Height: 1.5"

Stevie Bootie

A square-toe is an excellent choice for those seeking comfort, as the wide shape provides plenty of room for the tip of your foot. We're certain you'll want to wear these Franco Sarto boots on repeat—not only because of the forgiving shape, but also due to the warm mahogany hue suited to a fall palette.

Sizes: 5-11

Colors: Mahogany, black, grey, brown, dark brown, cream

Heel Height: 3.5"

Francesca Moto Boot

Have you heard the news? Biker boots are autumn's most coveted style and we've got just the right pair for you to stroll around in. Reformation's Francesca boots are constructed with waxed calf leather for a durable yet smooth feel, and the buckles are fastened loosely around the ankle so there's no need to worry about a tight fit.

Sizes: 5-11

Colors: Brown, black

Heel Height: 2"

Selpisa Knee-High Boot

Although you might not spend any time riding horses, you'll still appreciate the soft leather lining, low heel, and structured fit of Vince Camuto's equestrian-inspired boots. I especially love how the pebbled leather exterior displays a touch of texture and dimension.

Sizes: 5-11 (medium and wide calf)

Colors: Black, brown

Heel Height: 1"

Topstitched Velvet Ankle Boots

Proenza Schouler's lace-up boots have a unique zip fastening along the side, which makes putting on these shoes extremely convenient. Once these plush velvet boots are secured, you can then adjust the laces for a tighter fit if needed.

Sizes: 36-42

Colors: Black

Heel Height: 0.5"

Bubble Bootie

When I initially heard that red would be fall 2023's trending color, I wasn't fully on board. But I must admit, vibrant hues of rose, crimson, and burgundy are gradually piquing my interest, and I believe these Bottega Veneta booties might have just convinced me to fall for this fiery color.

Aside from the enticing shade, I also noticed the slip-resistant tread on the bottom of the shoe, which provides stability and support.

Sizes: 5-11

Colors: Red

Heel Height: 3"

The Benning Chelsea Boot

Madewell's Chelsea boots boast the brand's signature MWL Cloudlift Lite padding, a cushioned insole which works especially well for those who spend a lot of time on their feet. If you're in the market for an everyday shoe, this pair fits the bill with a classic design that will certainly compliment a variety of casual outfits.

Sizes: 5-12

Colors: Black, brown

Heel Height: N/A

Wally Suede Knee-High Boots

Wide-calf boots have been shining under the spotlight for quite some time now, and I don't think this style is going anywhere soon. Why would anyone want to forgo such comfort? The generous diameter of the shaft creates plenty of space for a fit that doesn't feel restrictive.

Sizes: 36-42 (6-10)

Colors: Black, olive green, pine green, plum, yellow, mahogany,

Heel Height: 0.5"

Gaston 75MM Suede Booties

I can't tell you the amount of times I've seen pointed boots on nearly every street corner of New York City, and I fully understand the appeal. There's something about an angular shape that instantly elevates any shoe while adding a dash of elegance. Case in point: L'AGENCE's Gaston 75MM Suede Booties, which convey a strong sense of sophistication while prioritizing comfort through a buttery leather lining and a padded insole.

Sizes: 5-12

Colors: Brown

Heel Height: 3"

Shale Knee-High Boot

With several pairs of Sam Edelman shoes in my closet, I can attest to the brand's ability to manufacture comfortable boots that last season after season. These knee-high boots are designed with a supple suede lining that offers an undeniable sense of flexibility.

Sizes: 5-11

Colors: Ivory, black, beige

Heel Height: 3"

Abba 38MM Leather & Shearling Lug-Sole Boots

If you're on the hunt for a comfortable pair of winter boots, we've got you covered. La Canadienne’s Abba boots are crafted with a fuzzy shearling lining to keep your feet warm all winter long. Pair them with a jeans, a turtleneck, and an oversized leather jacket for an effortlessly cool look.

Sizes: 5-11

Colors: Brown/ shearling

Heel Height: 1.5"

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