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Best Comfortable Boots for Men in 2023

Medically reviewed by Dr. Josh White, DPM - Written by OrthoFeet Team on Dec 26 2022

Just like good shoes, good boots need to be designed with features that will have you walking comfortably and pain free no matter what you do. 

However, there are additional features to consider if you are purchasing boots.

What are the most comfortable men’s boots?


Best Casual boots for men - Hunter Black

Hunter Black

Take on the outdoors in comfort and protection. Inspired with you and your busy day in mind, Hunter is a versatile boot for active adventures, spending all day on your feet or even lazy days in the backyard.

The upper is made from soft, waterproof leather that will keep your feet completely dry and in tip top shape, even in rugged terrain. 

A rubber toe guard provides further protection and guarantees your toes are safeguarded, if you accidentally bump into something.

A well-padded heel collar comforts the sensitive heel and ankle area and provides maximum cushioning with every step you take. 

On the inside, an entirely seamless construction is designed for feet with diabetes and neuropathy, and provides soft contact with the skin.

Hunter works wonders to help you walk better and improve your gait, because of the combination of anatomical arch, supportive cushioning, and mild rocker bottom sole. Your feet will no longer roll inward and each stride will require less effort and motion from the joints.

Hunter is also available in brown, which is not waterproof, and in widths ranging from Standard (D) to Extra Extra Wide (6E). Coupled with the wide last design and extra depth, your feet will enjoy a pressure free fit.

Shop Hunter Boot


Best Dress boots for men - Highline 

Highline Brown


Highline will be your staple dress boot as it can take on a classy look with a pair of chinos, but it can also be paired with jeans for a more casual look . 

The higher shaft construction will provide much needed ankle support and stability, incorporating substantial padding around the heel area. 

Furthermore, the inside of the boot features thick foam, which is enclosed in a soft and smooth lining that is seam free. This means they are suitable for diabetes or neuropathy, and you can rest assured they will not cause any friction or irritation.

Your feet will enjoy a relaxed and pressure free environment with the extra depth, wide last design, and generous forefoot shape. 

Whether you wear thick socks, have a protruding bunion, misaligned hammertoes, or foot swelling, Highline will deliver the utmost comfort as well as help minimize pain and discomfort from any of these conditions.

The premier orthotic, plus ergonomic sole combination will support your arch and straighten your feet, and rest of the body. 

Every step will be cushioned and impacts will be dispersed, because of the 5 hi-tech layers and unique air pocket design. 

You will finally be able to be on your feet pain free, no matter how long your day!

Highline is available in black and dark brown in Standard (D) to Extra Wide (4E) widths.

Shop Highline Boot


Best leather boots for men - Ranger

Ranger  zip brown

This unique boot provides the perfect solution for those who are looking for an easy and quick on-off wear. 

Thanks to ingenious two zippers at the heel, you can put the boots on and take them off in no time at all, without any effort and without the hassle of tying laces. It's as simple as sliding your foot in!

The sole is made from special rubber and constructed with a tread design that channels liquids away from the shoe, making it work well even on slippery surfaces. 

In addition, the lightweight, ergonomic, cushioning sole with a mild rocker design will make walking and standing a breeze. 

The toe box is wide and tall, which is perfect if you have bunions or hammertoes, or if your feet tend to swell, as your toes can move freely and lay in their natural position. 

The leather upper is soft and offers a relaxed fit, while the fabric, seam free interior protects even the most sensitive feet. 

The Ranger boots are bio-mechanically engineered to support and stabilize the ankle, and to enhance comfort. 

Available in Standard (D) to Extra Wide (4E) widths, and in black and brown.


Best work boots for men - Granite

Granite work boot

With a wide and roomy composite safety toe, F2413-18 safety rating, and impact, compression and electric hazard resistance - Granite are one of the best work boots out there. 

The leather upper is waterproof, but the boot is also designed with sealed seams and a gusseted tongue, to make sure no liquids seep in.

The rubber outsole is slip resistant, yes, even on oily surfaces, and is also designed with a very cool ladder grab feature that has notches, which latch onto ladder steps and greatly improve your stability. 

The ergonomic sole is cushioned from heel to toe, to ensure easy walking and reduce fatigue and stress on your feet.

The smooth fabric interior is padded with foam to protect sensitive feet, while a generously wide toe box not only enhances comfort for your toes, but also keeps them in check, so that they move naturally.

Extra depth and premium orthotics allow your feet to benefit from additional room and a relaxed fit.

Available in black and brown, and in widths ranging from Standard (D) to Extra Extra Wide (6E).

Shop Granite

Top Features for Comfortable Boots for Men


Orthotic support. The most comfortable men’s boots will be ones you can wear for 12+ hour days on your feet. 

This usually translates to boots that are designed with orthotic insoles to provide the greatest support for your arches. With that comes proper body alignment that includes the feet, knees, hips and back, and ensures you walk correctly, minimizing pain, discomfort and the possibility of unnecessary injuries. 

You will most likely find these boots from orthopedic footwear brands that pay particular attention to the biomedical design of their shoes.

Cushioning. Cushioning seems like a no-brainer, yet so many shoes today have a thin layer of a footbed resembling a piece of cardboard. And it’s not all about the thickness of the footbed either. 

Yes, the more layers the better, but there is much importance to the materials used. 

Shock absorbing materials that are able to disperse the forces along the bottom of the foot, as well as provide energy return will offer better pain relief and allow your feet to continue on without tiring easily.

Customized comfort. This feature is key if you want to get the most out of your boots and feel like they have been tailored to your feet. 

The best men's orthotic boots will have a footbed that is made with a type of foam or other material that is able to conform over time to the specific shape of your foot and gait, reducing pressure spots and offering a comfortable fit.

Interior construction. Seam free and padded interiors offer extra protection for those who have sensitive feet, such as neuropathy, arthritis and diabetes. Even a little thread can cause much irritation and be harmful for these types of feet.

Toe box. Do not buy boots with a pointy or narrow shape! Boots with a wide, round and tall toe box offer ample space for the toes to move biomechanically, accommodate hammertoes and bunions and provide a relaxed fit even if your forefoot swells.

Extra depth. Even though it might not seem like an important feature, a boot that has extra depth will make all the difference between one that is comfortable and one that is not. 

The added depth runs from the heel to the toe area and creates a relaxed fit, even if you have a high instep or wear thicker socks. If you wear braces or other orthotic devices, the extra room will come in handy.

Removable insole. How many times have you tried to pull the footbed out only to discover it is fused to the bottom? 

The best men's orthotic boots are designed with a removable footed that can be pulled out, so that you can insert a custom device if needed. 

Moreover, if you want to get that new shoe feeling after several months of use, you can simply replace the insole with a new one. 

Heel & tongue padding. Since boots have a higher upper design than an average sneaker or shoe, contact with the sensitive heel area is greater. Padding along the heel counter will prevent friction and blisters.

Outsole. Wet or icy conditions in cold weather pose increased risk of falling and injury. 

Make sure the orthopedic boots for men have a durable outsole to provide traction and stability, and help you walk comfortably.

Durability. Because boots are worn either in extreme weather conditions or demanding environments such as the workplace or the rugged outdoors, they need to be constructed with durable upper materials that will not fall apart or soil easily. 

And if they do get dirty, the option to clean them should exist and be effective. Materials such as leather or repelling fabric will be your best option. You can always increase protection by treating them with a protectant or waterproofing spray.

Adjustability. One of the easiest ways to ensure comfort in your shoes and boots is to purchase ones that will allow for a customized fit. 

Boots that have adjustability features such as laces, straps and bungee cords will hold your feet securely in position and prevent sliding around. 

But they also do much more than that. 

Boots with laces or straps allow you to tighten or loosen the fit around the instep. Since no two feet are the same, this is the perfect way to achieve a custom fit.

Insulation. The interior can be designed with a variety of materials. Boots for winter use will feature insulating materials, such as faux fur or shearling, to retain heat and prevent your toes from being exposed to extreme temperatures. 

This is extremely important for individuals who also have neuropathy and have lost sensation in their feet and toes.

What are the benefits of boots?


Seeing as boots have height, one of their main benefits is the protection they give your ankles. 

This protection can come in two forms:

  1. Support that helps prevent injuries, such as twisting your ankle, spraining and even breaking it. 
  2. Cushioning from any type of impact. 

Another big benefit is that boots are very sturdy and strong footwear. 

Can you walk in boots all day?


If your boots fit you properly and don’t cause you pain or foot problems, there is no downside to wearing your boots all day long. 

And if your boots offer all the design features mentioned above, they will feel so comfortable on your feet that you might not want to take them off, even when it’s time to put your feet up. 

Should you wear the same boots everyday?


It’s always a good idea to rotate your boots and allow them to rest between uses, so that they don’t wear out quickly.  

In addition, if your boots are damp at the end of the day, allow them enough time to dry, to prevent bacteria and odors. 

But, unless you sweat a lot, the typical boot will dry overnight and you can safely wear it again the next day. Good boots have innovative features that prevent moisture from building up inside, keeping your feet clean and dry. 

How do I make my boots more comfortable?


The best way to make boots more comfortable is, well, to buy the right boots to begin with.

But, if your new boots are causing blisters or hurting your feet, try the following steps:

  • Wear padded socks to help reduce friction and prevent blisters.
  • If the boots are too tight, try widening them with an at-home stretcher or a stretch spray. Try loosening  the laces or straps a tad, but not too much so that your foot slips, to release some pressure.
  • Add orthotics that can support your feet and reduce pressure points. 
  • Add an Arch Booster to enhance support under the arch. 
  • Insert fitting spacers to customize and tighten the fit inside every shoe.