What Are the Most Comfortable Work Boots?

Being comfortable during the work day is a necessity, especially if you’re working long hours. If your feet hurt throughout the day, then your day seems to drag on much longer. No worries, we break down which boots are the most comfortable and other features of the most comfortable work boots!

We grade each boot on four different categories from one to five; Comfort, Warmth, Durability, and Rain/Snow Repellency.

Comfort in a boot relies heavily on the outer sole of the boot, along with where the boot will be used. For example, a soft sole with lots of give is great for indoor environments, although it isn’t great for constant outdoor use in uneven terrain. 

Also, the same soles are used on multiple different styles of boots. Therefore, there are boots that have the same soles and in different categories, but these styles could be swapped between both categories and still be true. For example, the 2406 and 2412 both have the same sole, and are in two different categories, but that’s not to say that they can’t be swapped.

PLEASE NOTE:  The overall score is based on the average of four categories; Comfort, Warmth, Durability, and Rain/Snow Repellency. The boot that ranks the highest in overall, may not be the boot for you. For example, a comfortable shoe will not grade high in warmth, durability, or rain/snow repellency, making the overall score low. Although, this shoe will be ranked the highest in comfort and will be a great shoe for light-duty work indoors.

Overall Most Comfortable Boots


Most Comfortable Work Boot - 83832

Irish Setter Wingshooter ST - 83832

This Irish Setter Work boot is one of the most comfortable boots made by Irish Setter. The wedge sole is very soft to give a plush feeling. 

The Irish Setter Wingshooter boot is graded a two in Warmth. This boot has a waterproof liner, which still allows the foot to breathe, but is a bit more warm than just a solid leather upper.

We graded the durability of this boot a 4.5. The Wingshooter is made with a Goodyear welt, which provides the boot with substantial durability. You will see lots of boots with this Goodyear welt on this list. The only reason this is not a 5 is because of the soft sole, which is prone to wearing out faster because of how soft it is.

The Wingshooter was graded a 4.5 in Rain/Snow repellency. This boot has a waterproof membrane inside, which allows you to stand in puddles or piles of snow. The only reason this boot is not a perfect 5 in this case is because we grade a boot with Gore-Tex liner as the most superior.

Best Uses: Walking or standing on hard surfaces for long periods of time.

Worst Uses: Outdoor Uneven Terrain, or Constant Ladder Climbing


Most Comfortable Work Boots - 814-4178

Thorogood American Heritage Moc Toe - 814-4178

Thorogood is known for their Made in the USA Wedge Boots, this being one of the best. The American Heritage Moc Toe boot has a very soft sole, again making it one of the most comfortable boots on the market. Scoring a perfect 5.

This American Heritage Moc Toe boot is graded a 1 in the warmth category, due to having no liner. Making this a perfect boot for summer or indoor use.

The 814-4178 is constructed with an extremely durable Goodyear welt. Once again, a great score of 4.5, again due to the softer sole.

In the category of Rain/Snow Repellency, this boot is graded a 3. Even though it doesn’t have a waterproof liner, leather is naturally water resistant. We don’t suggest you stand too long in water, as it will eventually soak through, but if you plan on just walking through water quickly, you won’t have anything to worry about.

Best Uses: Walking or standing for long periods on hard surfaces. Great for summer or indoor use. 

Worst Uses: Outdoor uneven terrain or constant ladder climbing.


Most Comfortable Work Boots - 2412

Red Wing Shoes SuperSole 2.0 - 2412

Red Wing Shoes is a premier work boot company, making some of the finest work boots. 

The SuperSole 2.0 boots are all made with a comfortable dual density outsole. A very soft inner part of the outsole allows for great relief while walking or standing for long periods of time. The outsole is still a soft material, although is more durable and provides more protection than the inner density. 

The 2412 was graded a 3 of 5, since it is lined with 400g of Thinsulate (the leader in insulation for clothes and boots). The 400g is considered the happy-medium of insulation, since it can be used for both summer and winter.

In Durability, we rated this boot a 4.5. The Red Wing 2412 has a direct attach welt construction, making it the perfect balance of durability and flexibility. Also made with a full-grain leather, this boot is made to take a beating day in and day out. 

The 2412 is made with a Gore-Tex lining, giving the boot a perfect rating of 5 in the Rain/Snow repellency category. The Gore-Tex Membrane has BILLIONS of pores, each of which is 20,000 times smaller than a water droplet! That means standing in water all day long is an easy job for this boot, and is even guaranteed. Making this one of the best waterproof work boots.

Best Uses: Any job outdoors that requires constant walking, crouching, or standing on hard surfaces. Plan on doing lots of climbing on ladders, no worries, this boot also has a 90º wedge. This allows for more support and stability on ladders.

Worst Uses: Uneven Terrain


Most Comfortable Work Boots - TB0A29G9

Timberland Pro Boondock HD - TB0A29G9

Timberland Pro is known for their famous “yellow” boot. Although, they should be better known for their Boondock series boots.

Rated a perfect 5 in comfort, these boots shine in the outdoors on uneven terrain. That’s because of the harder outsole, allowing for less flexibility and bend from uneven environments. Also, with their StepPropel insole, these boots transfer energy back to you with every step.

In the category of warmth, we rank the Boondock a two. The waterproof liner provides a bit of protection from the cold, but not nearly as much as an insulated pair. If you’re looking for this same style, except insulated, check out these here: TB0A28SB 

Along with other boots on this list, we rank this boot a perfect 5 for durability. The goodyear welt construction is extremely durable. Paired with the harder outsole, you won’t be wearing these things out fast at all.

Again, lined with a waterproof membrane, these boots are ranked a 4.5. These boots have no problem being worn in any type of weather, from rain to snow. 

Best Uses: Uneven terrain, or climbing. 

Worst Uses: Long hours of standing on concrete.