The Best Comfortable Boots for City Walks, Dinner Dates, and Outdoor Adventures (2024)

The Best Comfortable Boots for City Walks, Dinner Dates, and Outdoor Adventures (1)

Boots are a wintertime footwear essential thanks to a blend of protection from the elements, stability, and warmth. Since you’ll likely be wearing them a lot, they should be comfortable, too. So how do you choose the right pair? Understanding the nuances of different materials, from leather to synthetics, is key to balancing longevity with comfort. Support and sizing are crucial, too.

"Boots that combine comfort and style are essential for tackling the day with confidence," says stylist Janelle Tan. “A good pair of comfortable boots offers the perfect blend of support and fashion, making them a versatile choice for any occasion."

To help you determine which boots are best for navigating winter weather, we spent hours combing through options for every occasion. Whether you’re braving the city streets or exploring the great outdoors, the right pair of boots can make all the difference. We also tapped Tan for expert tips on what to look for when shopping.

Our Top Picks

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Best Comfortable Boots for Hiking:

Merrell Waterproof Hiking Boots at Amazon ($117)

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Best Overall Comfortable Boots

Blundstone Women's Style 558 Chelsea Boots

The Best Comfortable Boots for City Walks, Dinner Dates, and Outdoor Adventures (2)

What Stands Out

  • The shock absorption is exceptional, significantly reducing impact for walking and prolonged wear.

What Could Be Improved

  • A wider range of colors and styles.

The Blundstone Women's Style 558 Chelsea Boots have a simple and streamlined yet functional elegance to them. These boots stand out for their exceptional comfort and shock absorption capabilities, absorbing up to 90% of impact as you walk, which is a significant advantage for those who spend long hours on their feet. This feature alone makes them a go-to choice for daily wear, combining practicality with a classic aesthetic.

These boots are crafted from premium leather, offering both durability and a supple feel for superior comfort. The pull tabs make slipping these boots on and off easy, which is ideal for those who may need to remove their footwear often throughout the day. They are weather-ready with water-resistant leather, too, making them suitable for various outdoor conditions. The double stitching and tough outsole add to their longevity, which means the investment you make in these boots will pay dividends for years to come.

Size Range: 6-11 | Material: Black premium water-resistant leather | Heel Height: N/A | Shaft Height: N/A

Best Budget Comfortable Boots

Cushionaire Women's Sasha Chelsea Boot with Memory Foam

The Best Comfortable Boots for City Walks, Dinner Dates, and Outdoor Adventures (3)

What Could Be Improved

  • A more robust sole design for enhanced traction and durability would elevate their practicality for diverse terrains.

The Cushionaire Women's Sasha Chelsea Boot is an excellent choice for those looking for budget-friendly footwear without sacrificing comfort and style. These boots are notable for their memory foam insoles, which provide ample comfort and support. The boots' elastic side panels not only add to the visual appeal but also ensure a snug and customizable fit, making them easy to slip on and off. The faux leather material offers a sleek and stylish look while also being easy to clean and maintain.

While these boots are comfortable and affordable, a sole with better traction would make them more suitable for a variety of outdoor activities and terrains. These upgrades would make these already excellent boots even more versatile. Overall, they stand out as a top budget-friendly option, combining comfort, style, and practicality in one package.

Size Range: 6-11 | Material: Rubber, faux leather | Heel Height: 2 inches | Shaft Height: N/A

Best Comfortable Heeled Boots

Aerosoles Cinnamon Black Ankle Boot

The Best Comfortable Boots for City Walks, Dinner Dates, and Outdoor Adventures (4)

What Stands Out

  • A signature diamond flex outsole and a stretch upper that conforms to the foot.

What Could Be Improved

  • Adding more cushioning in the insole could further enhance their appeal for all-day wear.

The Aerosoles Cinnamon Black Ankle Boot combines fashion-forward design with practical features, making it an excellent choice for those seeking both style and comfort for everyday wear or a night out on the town. The boot's stretch upper material adapts to the shape of the foot while the signature diamond flex outsole offers flexibility and traction, making them suitable for various settings, from everyday wear to evening events. The sturdy block heel also makes for a comfortable height boost without compromising stability, making these boots ideal for prolonged wear.

The boots could benefit from added cushioning in the insole which means that it might not be a perfect choice for anyone planning to walk long distances. That said, these boots are an excellent choice for anyone who wants to be comfortable while getting a little lift from their boots.

Size Range: 5-12 | Material: Stretch | Heel Height: 2.75 inches | Shaft Height: 6 inches

Best Comfortable Platform Boots

Steve Madden Hayle Platform Chelsea Boot

The Best Comfortable Boots for City Walks, Dinner Dates, and Outdoor Adventures (5)

What Stands Out

  • Chic street style and an easy slip-on design.

What Could Be Improved

  • A wider variety of colors.

Steve Madden’s Hayle Platform Chelsea Boot is a modern take on the classic Chelsea boot that perfectly blends style and comfort. The boots have an attractive synthetic suede-looking upper, and the textile lining makes them particularly comfortable, especially for extended wear. Most importantly, the synthetic footbed offers good support for the feet.

The easy slip-on style, complemented by a round toe and a stacked block heel, makes these boots both stylish and convenient to wear. The synthetic outsole also provides good traction and a slight lift for a bit of elevation that is still suitable for longer walks. This design strikes a balance between fashion and functionality, offering a trendy option for Chelsea boot fans. They do currently come in a limited selection of colors, and expanding this range would allow them to appeal to a wider audience with varying style preferences for this already popular and high-quality style.

Size Range: 6-11 | Material: Synthetic upper, lining, and sole | Heel Height: 2.25 inches | Shaft Height: 6.25 inches

Best Comfortable Boots for Hiking

Merrell Waterproof Hiking Boots

The Best Comfortable Boots for City Walks, Dinner Dates, and Outdoor Adventures (6)

What Stands Out

  • All-day comfort and a robust build quality that makes it an excellent choice for both day hikes and light backpacking.

What Could Be Improved

  • Despite its strengths, the boot is on the heavier side, which may affect agility and nimbleness on more technical trails.

Merrell’s Moab 3 Women's Hiking Boot is our top choice for hikers thanks to its comfort, durability, and versatility. A key update in this model is a more supportive insole and a softer, more cushioned midsole, which makes these boots even more comfortable for extended hikes. The Vibram TC5+ outsole also gives exceptional traction for various outdoor activities, and the boots were constructed with environmentally friendly materials like breathable mesh upper made from 100% recycled materials, including the laces and webbing. The boot features a bellows tongue to keep out debris, a protective rubber heel and toe cap for added durability, and a Merrell Air Cushion in the heel for shock absorption and stability.

The Moab 3s are notably heavier compared to some modern hiking shoes, which may be a drawback for hikers who prefer a lighter feel or are embarking on longer or more challenging hikes. Overall, the Merrell Moab 3 Women's Hiking Boot stands out as an excellent choice for those who want to take comfortable hikes with its eco-friendly construction adding an additional layer of appeal for environmentally conscious consumers​.

Size Range: 5-12 | Material: 100% recycled laces, webbing, and mesh lining | Heel Height: N/A | Shaft Height: N/A

Best Comfortable Winter Boots

The North Face Women's Thermoball Lace-Up Waterproof Boots

The Best Comfortable Boots for City Walks, Dinner Dates, and Outdoor Adventures (7)

What Stands Out

  • Exceptional insulation and waterproofing that ensure warm and dry feet in harsh winter conditions.

What Could Be Improved

  • A more streamlined design could enhance their appeal.

The North Face Women's Thermoball Lace-Up Waterproof Boots are designed to keep your feet warm and dry in the coldest and wettest of conditions. These boots are equipped with advanced insulation technology, featuring the brand's proprietary Thermoball Eco insulation, which makes for warmth even in wet conditions. The waterproof construction further ensures that your feet stay dry, making these boots ideal for snowy and rainy winter days. The high-traction rubber outsole also offers reliable grip on slippery surfaces, which is particularly important in the winter.

The design could be more streamlined, as a sleeker, more fashion-forward look would broaden their appeal. But for less dressy occasions when snow is piling up, North Face boots are a top choice for winter, offering unbeatable protection against cold and wet conditions.

Size Range: 5-11 | Material: 5% recycled rubber content and 8% plant-derived bio-oil | Heel Height: N/A | Shaft Height: N/A

Best Comfortable Rain Boots

Hunter Women's Refined Tall Rain Boots

The Best Comfortable Boots for City Walks, Dinner Dates, and Outdoor Adventures (8)

What Stands Out

  • A chic design with matte gold hardware and a streamlined, slim fit that flatters the leg.

What Could Be Improved

  • The boot's height may be too tall for shorter people and cause discomfort at the back of the knees.

The Hunter Women's Refined Tall Rain Boots stand out for their elegant and polished design, featuring an alternative eyelet buckle in matte gold that adds a stylish touch. These boots are crafted from FSC-certified natural rubber, which means that they are 100% waterproof while aso adhering to sustainable and environmentally friendly standards. To a similar note, the lining is made of recycled polyester.

The streamlined design and slimmer fit make these boots less bulky and more flattering on the leg compared to traditional rain boots, and the refined silhouette makes them versatile for both countryside walks and city strolls. Despite their fashion-forward design, these boots maintain the practicality expected from a rain boot, providing excellent waterproof protection in wet conditions.

Note that the height can cause issues for shorter people, as this can lead to the boots rubbing against the back of the knees while walking. But overall, Hunter’s rain boots are stylish, waterproof, and sustainable, while also being extremely comfortable, offering a stylish and practical solution for rainy days.

Size Range: 5-11 | Material: 100% waterproof and fitted with 100% recycled polyester linings | Heel Height: N/A | Shaft Height: N/A

Best Comfortable Combat Boots

Thursday Women's Combat Boot in Black Leather

The Best Comfortable Boots for City Walks, Dinner Dates, and Outdoor Adventures (9)

What Stands Out

  • A sleek design with a full-grain leather upper and full glove leather interior lining for comfort.

What Could Be Improved

  • The cemented construction means they are not waterproof or resoleable, which might limit their longevity compared to traditionally constructed combat boots.

Thursday’s Women's Combat Boots are stylish, comfortable, and durable. They are made from full-grain leather sourced from Lefarc Tannery in Mexico, one of the most sustainable leather manufacturers in the world. This quality leather starts out a bit stiff but breaks in quickly, offering comfort in days or even hours, unlike other boots that may require much longer. The interior lining is also crafted from full glove leather, which enhances the overall comfort of the boot.

The boots feature shock-absorbing memory foam insoles that conform to the shape of your feet, providing all-day comfort. The durable rubber outsoles offer extra grip on various surfaces, making these boots practical for different environments. The premium waxed cotton laces are not only stylish, but also functional, as their flat design helps them stay tied.

However, one of the notable limitations of these boots is their construction. They are cemented, which means the top is glued to the sole rather than stitched. While offering comfort, flexibility, and a lighter feel, this also means they are not waterproof or resoleable. This construction might affect the long-term durability and practicality of the boots in harsher weather conditions. But overall, these boots are an excellent pick for anyone looking for a stylish, comfortable, and quick-to-break-in combat boot.

Size Range: 5-12 | Material: Black Full-Grain Leather | Heel Height: 1.5 inches | Shaft Height: 6 inches

Best Comfortable Riding Boots

Naturalizer Rena Wide Calf Riding Boot

The Best Comfortable Boots for City Walks, Dinner Dates, and Outdoor Adventures (10)

What Stands Out

  • The combination of a wide calf design and Contour+ technology for a comfortable, custom fit, suitable for long hours of wear.

What Could Be Improved

  • Incorporating a more diverse range of colors and finishes would cater to a wider array of personal styles and preferences.

The Naturalizer Women's Rena Wide Calf Riding Boot blends style, comfort, and practicality. These boots feature a wide calf design, making them accessible and comfortable for a variety of leg shapes, which is often overlooked in standard riding boots. The inclusion of Naturalizer's innovative Contour+ technology also ensures a comfortable fit that adapts to your foot, providing all-day comfort. This is particularly beneficial for riders who spend extended periods in the saddle or on their feet.

Made from premium leather, these boots offer durability and a classic, polished look that is synonymous with quality riding attire. They aren’t available in a wide range of colors and finishes, so those who might be looking to make a bolder statement with their riding boots would have to look elsewhere. That said, these boots are a comfortable and elegant pick that will have you striding or riding in style wherever your day holds.

Size Range: 4-13 | Material: Leather or leather/suede upper with an almond toe | Heel Height: 1.25 inches | Shaft Height: 14.8 inches

Best Comfortable Knee-High Boots

Vivaia Madeline 2.0 Water-Repellent Wool Over-the-Knee Boots

The Best Comfortable Boots for City Walks, Dinner Dates, and Outdoor Adventures (11)

What Stands Out

  • Water repellent wool allows you to step out in style in any weather.

What Could Be Improved

  • They may fall down below the knee as you’re walking.

Vivaia’s Madeline 2.0 boots have all the elegance or traditional knee high boots while also being comfortable and practical. A key feature of these boots is the water-repellent wool, which offers durability and comfort and makes the boots suitable for many weather conditions. And the over-the-knee design not only makes for a fashionable silhouette, but it also provides extra warmth during cooler months.

The boots are designed with a soft and flexible sole, which makes them a good choice for longer wear. They are also made with eco-friendly materials, which can assuage those who want to look good while keeping environmental considerations in mind. The wool composition is beneficial for water resistance, but it might require more care in cleaning compared to synthetic materials. Vivaia’s boots strike an ideal balance between fashion-forward design and functional features, making them a noteworthy option for those looking for a comfortable yet stylish knee-high boot.

Size Range: 35-43 | Material: Breathable and soft uppers made from water repellent ethical wool yarn | Heel Height: 1.18 inches | Shaft Height: 22.4 inches

Best Comfortable Shearling Boots

Overland Women's Hudson Shearling-Lined Waterproof Leather Boots

The Best Comfortable Boots for City Walks, Dinner Dates, and Outdoor Adventures (12)

What Stands Out

  • The genuine shearling lining, which offers exceptional warmth and comfort, ideal for cold weather.

What Could Be Improved

  • The boots could benefit from incorporating vegan or more sustainable materials to appeal to eco-conscious consumers.

The Overland Women's Hudson Shearling-Lined Waterproof Leather Boots are luxurious yet practical, making them a standout choice for shearling boots. The genuine shearling lining is a highlight, as it offers exceptional warmth and comfort that is ideal for cold weather. This natural material provides better insulation compared to synthetic alternatives, which will work to keep your feet cozy, even in freezing temperatures.

Another notable feature is the waterproof leather exterior. This high-quality material construction ensures the boots are durable and suitable for various weather conditions, from light rain to heavy snow. The classic design of these boots, with a focus on functionality and comfort, makes them versatile for both casual and more formal winter attire.. These boots are an excellent choice for those seeking warmth, comfort, and style in their winter footwear no matter how cold or snowy the temperatures outside.

Size Range: 36-43 | Material: Tall waterproof suede and leather boots with shearling shaft and wool footbed | Heel Height: 1.50 inches | Shaft Height: 13.5 inches

Best Comfortable Boots with Arch Support

Vionic Brighton Ankle Boot

The Best Comfortable Boots for City Walks, Dinner Dates, and Outdoor Adventures (13)

What Stands Out

  • An orthotic footbed designed for enhanced arch support, and a sleek and versatile design that makes them suitable for various occasions.

What Could Be Improved

  • The tight fit, though it stretches over time with wear.

Designed specifically to cater to foot health, these boots incorporate an innovative orthotic footbed. This feature is engineered to provide biomechanical support that is particularly beneficial for people with flat feet or plantar fasciitis. The footbed aligns the feet to their natural position, reducing strain on the knees, ankles, and back, making them an ideal choice for extended wear.

Aesthetically, the boots have a sleek and versatile design, which makes them suitable for various occasions, from casual outings to more formal events. The leather upper gives them a polished look, and the inclusion of a side zipper not only adds to the style, but it also makes them easy to put on and take off.

For those without specific foot issues, the pronounced arch support and initial tightness might feel unfamiliar or uncomfortable at first. But for those who do want arch support, Vionic’s Brighton Ankle Boot is an excellent choice. Their combination of style, support, and quality materials make them a valuable addition for anyone who wants to prioritize foot health while shopping for shoes.

Size Range: 5-11 | Material: Suede | Heel Height: 1.37 inches | Shaft Height: 5 inches

Best Comfortable Sock Boots

Naadam Knit Boot

The Best Comfortable Boots for City Walks, Dinner Dates, and Outdoor Adventures (14)

What Stands Out

  • Sock-like comfort with the structure of a boot, made from a luxurious cashmere blend.

What Could Be Improved

  • The delicate nature of the cashmere material might require more maintenance and may not withstand harsh weather or rough outdoor activities.

Naadam’s Knit Boot offers a modern twist on traditional boot styles, blending the comfort of a sock with the structure of a boot. Crafted from a luxurious cashmere blend, these boots are soft and warm, making them an ideal choice for anyone looking to get cozy. The knit design makes for a snug fit, adapting seamlessly to the shape of the foot. Unlike more rigid boots, these are easy to move in, making them suitable for both indoor and casual outdoor wear. The minimalist, sleek design also makes them a versatile fashion item, easily paired with a variety of outfits.

However, the delicate cashmere material may require more careful maintenance than traditional leather or synthetic boots, and they might not be suitable for harsh weather conditions or rough outdoor activities. But the boots are an excellent choice for anyone prioritizing comfort and style in a lightweight, cozy form.

Size Range: 6-10.5 | Material: 50% recycled polyester, 20% wool, 20% polyester, 10% elastane | Heel Height: N/A | Shaft Height: N/A

Final Verdict

The Blundstone Women's Style 558 Chelsea Boots are our pick for the best overall comfortable boots thanks to their timeless design and exceptional comfort and shock absorption. For a pocket-friendly pair with comfortable memory foam, we recommend the Cushionaire Women's Sasha Chelsea Boot with Memory Foam.

How to Shop For Comfortable Boots Like a Pro


When shopping for comfortable boots, it's important to understand the various styles of boots and their distinctive features. Chelsea boots are versatile ankle-high options with elastic side panels that are perfect for both casual and formal settings. Riding boots are elegant, knee-high, and should be calf-width, especially for layering over pants. Combat boots are rugged and durable with supportive lace-up designs, ideal for stability and ankle support. Heeled boots vary in height; opt for block heels and cushioned footbeds for comfort. Wedge boots combine height with stability and are an excellent choice for those who prefer elevation without discomfort. Snow boots—essential for cold, wet conditions—should be waterproof and insulated, while hiking boots require good traction, support, and breathable materials. Lastly, sock boots offer a modern, form-fitting style with breathable material and adequate cushioning.


When picking out a pair of comfortable boots, the material is an important factor to consider. Leather boots, which are renowned for their durability and timeless appeal, mold to your feet over time, which makes for a customized fit. “Good-quality, soft leather reduces the dreaded ‘break-in’ time with a new pair of boots,” Tan says. However, leather requires regular maintenance to preserve the look and feel. Suede, a softer leather variant, adds a luxurious texture but can be challenging to maintain in wet conditions.

Synthetic materials like faux leather offer a vegan alternative and often come with easier maintenance and lower costs, though they may lack breathability compared to natural materials. For harsh weather, waterproof materials like Gore-Tex are essential for keeping feet dry, while wool or fleece linings add warmth for winter wear. Breathable fabrics like mesh are ideal for hiking boots to ensure comfort during active use. Ultimately, the right material balances durability, comfort, and suitability for your intended use and personal values, like sustainability or animal welfare.


Support is a key element to consider when shopping for comfortable boots. Good support can significantly reduce foot fatigue and discomfort, especially when wearing boots for extended periods. Look for boots with well-designed arch support, which is crucial for maintaining proper foot alignment and preventing issues like plantar fasciitis. Ankle support is especially important in certain styles, like combat or hiking boots, to provide stability and prevent injuries. Cushioned insoles can make a big difference in overall comfort, as they absorb impact and reduce stress on your feet. Some boots offer removable insoles, allowing you to use custom orthotics for personalized support. Additionally, a sturdy sole with good traction is essential for safety and comfort, particularly in wet or uneven terrain. When trying on boots, pay attention to how your feet feel in terms of support and alignment, as this can greatly impact your comfort and foot health over time.

Sizing and Fit

When shopping for boots, proper sizing and fit are essential for comfort and foot health. A good fit means enough space to wiggle your toes without the boot feeling loose, ensuring both comfort and support. It's important to try on boots with the socks you intend to wear, considering both length and width. Sizing can vary across brands and styles, so always check the brand's size guide, especially for specific styles like riding or knee-high boots, which may require different calf sizes. Materials like leather should feel snug but not overly tight, as they will mold to your foot over time. Pay special attention to the heel area to prevent slipping and avoid any rubbing or pinching, as well as toes and ankles.

Questions You Might Ask

What are some brands that specialize in comfortable shoes?

Several brands have made a name for themselves by prioritizing comfort without sacrificing style. “If you want a pair of comfortable shoes, go with shoes that runners and healthcare workers wear,” Tan says. “These tend to be shoes that have arch support and shock absorption. I love the brand ECCO, and I also love Clarks.” Skechers offers a wide range of casual shoes with memory foam padding, which is ideal for those who are on their feet all day. Birkenstock, which is famous for its contoured cork footbeds, provides exceptional support, which is particularly beneficial for those with foot ailments. Vionic is another standout, offering stylish shoes with built-in orthotic support, a boon for people with arch issues. Lastly, brands like Dr. Scholl's and New Balance are well-regarded for their focus on foot health, offering a variety of comfortable options that cater to different needs, from fashion-forward designs to athletic and therapeutic footwear.

How do you know if boots fit correctly?

Knowing if boots fit correctly is critical for comfort and foot health. A well-fitted boot should feel snug but not tight, allowing enough room to wiggle your toes. “The easiest way to tell is to place your finger between the back of your ankle and the back of your boot. There should be just enough space for your finger to fit,” Tan says. “You should also be able to move your toes comfortably.” There shouldn't be excessive space at the front of the boot, as this can cause your feet to slide forward, but your toes shouldn't touch the front end either. The width is also important; the boots should not pinch or squeeze the sides of your feet. In the heel area, a small amount of slippage is normal in new leather boots, but excessive movement can lead to blisters. The instep should feel secure and comfortable, not overly tight or loose. When you walk, your heel should lift slightly with each step, but the boot shouldn’t slip off. Lastly, consider the boot's arch support; it should align with the arch of your foot, providing support without causing discomfort. Trying boots on in the afternoon, when feet are typically at their largest, can help ensure a better fit. Remember, comfort should be immediate; if the boots are uncomfortable in the store, they likely won't improve with wear.

How much do high-quality, comfortable boots cost?

The cost of high-quality, comfortable boots typically ranges from $100 to $300, influenced by factors like brand reputation, material quality, and specialized features like waterproofing or orthotic support. “You're paying for leather quality and sole quality (shock absorption and arch support),” Tan says. “Don't skimp on your feet!” Premium options, especially those from brands or made with top-tier materials like genuine leather, can exceed $300, sometimes reaching $500 or more. While budget-friendly alternatives exist, they may not offer the same durability or comfort, potentially leading to more frequent replacements and higher long-term costs. Investing in a more expensive, well-constructed pair can be economical over time, particularly for daily wear or specific activities like hiking. Shopping during sales or looking for discounts on reputable brands can help balance quality and affordability.

Why Trust Real Simple

This article was written by Elizabeth Loomis, a seasoned writer who has spent years covering lifestyle topics that have given her a discerning eye for what makes a gift both delightful and memorable. From her time reporting on the latest trends in interior design for The Zoe Report to her work exploring the dynamic world of beauty for InStyle, she's developed an understanding of how aesthetics and functionality can merge to create standout products. Her expansive coverage of lifestyle topics for Well + Good, The Spruce, and other lifestyle publications has further enhanced her sense of the beautiful, the functional, and the unique. To compile this list, she spoke with stylist Janelle Tan, and combed through countless products to bring you the best of the best.

The 25 Most Comfortable Shoes of 2024

The Best Comfortable Boots for City Walks, Dinner Dates, and Outdoor Adventures (2024)
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