Best Comfortable Boots for Men in 2021

Medically reviewed by Dr. Josh White, DPM - Written by OrthoFeet Team on Jan 13 2021

Perhaps you live in an area that has distinct seasons and a winter climate, or maybe you’re just looking for more coverage and protection in your busy day to day. 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 for other purposes such as ones to wear in subzero temps, in work environments or maybe due to a foot condition you have.

In this blog we will look at all the important elements the best comfortable boots for men need to have and recommend a few styles we guarantee will become your favorites.

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 the growing number of 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 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: We do not pay too much attention to this feature but whether a boot 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 for edema, if you have a high instep or wear thicker socks.

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.

Heel & tongue padding: Since boots run higher 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, stability and help you walk comfortably.

Durability: Because boots are worn either in extreme weather conditions or demanding environments such as the workplace, 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 exists and is 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 do much more than that. Boots with laces or straps allow you to tighten or loosen the fit around the instep or heel. Since no two feet are the same, this is the prefect 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.

Our List of Best Comfortable Boots for Men in 2021


Hunter Brown

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, long hours on your feet or even lazy days in the backyard.

The upper is made from durable synthetic material that will keep your feet in tip top shop even in rugged terrain. A rubber toe guard provides further protection and guarantees your toes are safeguarded if accidentally bumping 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 diabetic and neuropathic feet 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 support, supportive cushioning, and mild rocker bottom sole. Your feet will no longer roll inwards, and each stride will require less effort and motion from the joints.

Hunter will fit wide width feet since it is available in extra wide. Coupled with the wide last design and extra depth, your feet will experience a pressure free fit.

Shop Hunter


Highline Boot

Tough for hard-working days yet, flexible and super comfortable for everyday use. Highline will be your staple boot as it can take on a classy look with a pair of chinos or causal look while on the job. It is chosen time over time as the best comfortable work boots.

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.

While providing comfort is essential, correcting the foot issue is even more important as it is the root of the symptoms. 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 pebbled black leather and smooth brown.

Shop Highline Boot

Glacier Gorge


A classic boot in soft full grain leather upper, Glacier Gorge is a “slip and go” boot thanks to the two hook and loop straps across the instep that provide easy on/off wear. This also enables you to tighten and loosen the straps according to your foot shape, size, and grip preference. The tongue completely opens and pulls back which makes inserting your foot effortless.

With all the features included in this styles, Glacier Gorge will be your most comfortable men's boots for walking.

First and foremost, the Ortho-Cushion System that is designed in every shoe is a unique system that is comprised of superior cushioning and premium arch support to provide the ultimate comfort for all types of feet and foot conditions. Heel pain, plantar fasciitis, Achilles tendonitis and flat feet will benefit from the orthotic insole that will align the body from the ground up and control overpronation. The ergonomic sole that is ever so slightly angled from the heel to toe, ensure easy walking by transferring weight and reducing direct pressure upon heel strike.

A generously wide toe box not only enhances comfort for your toes but also keeps them in check so that they move biomechanically. If you happen to have a bunion or hammertoe, the extra space will not put any further pressure on them and deteriorate the condition.

Extra depth and a removable orthotic cater to those who need to insert a custom device to treat other conditions. And in case you do not, your feet will benefit from additional room and a relaxed fit.

Shop Glacier Gorge