Best Red Wing Work Boots of 2020: Top Five Picks

Best Red Wing Work Boots -

Having the right type of footwear when you get out there working may seem like the last thing you should be concerned with. However, without the right pair of boots, you may find yourself suffering from severe pain throughout the day or even experiencing unnecessary injuries.

There are a lot of great brands and options when you begin looking for a good pair of work boots. As you do your research, we are sure you will run into shoes made by Red Wing. This is one of the best known and most reputable brands in the work boot industry.

Red Wing has been crafting premium-grade footwear for over a hundred years and was even the go-to brand for the servicemen of both World Wars. There are a lot of great models from this Minnesota-based company, so we decided to put together a comprehensive list of some of the best Red Wing work boots on the market today.

Below we take an in-depth look at five of these in the hopes that we can help you make your decision-making process just a little easier. So let's get right to it.

Comparison Chart

Red Wing Heritage Men’s Classic 1907 Boot

Red Wing Men’s 6668 Steel Toe Boot

Red Wing Men’s Heritage Work Chukka Boot

Red Wing Men’s Steel Toe Logger Work Boots

Red Wing Heritage Men’s Iron Ranger Work Boot

Best Red Wing Work Boot Reviews

Red Wing Heritage Men's Classic 1907 6-Inch Moc Toe Boot

Our first entry is a rugged and durable classic 6” moc boot. Crafted with care to ensure not only function but style, this boot easily found its way onto our list.


Some features have to be present to make a god work boot. Red Wing understands this and has always delved a well-crafted work boot. This model includes the following features:

  • Shaft measurement – 5.5” from arch
  • Opening measurement – 6”
  • Heel height – 1”
  • Weight – 2.5 lbs.
  • Crafted with weather-resistant full-grain uppers
  • Naturally wicking smooth leather lining
  • Leather footbed
  • Outsole designed for shock/vibration absorption
  • Crepe style outsole enhances traction and support

There is a lot to love about this work boot. The Heritage Moc boot is an ankle-high boot that starts with high-quality materials and ends with a boot that offers you a good amount of protection and comfort.

The materials used in the design of the boot brings with it durability and life as well. Many work boots are clunky and ugly, but Red Wing prides itself on giving you a stylish and functional boot, and that is what the Heritage 6” Moc boot is.

However, even with all of those advantages, there are a few issues that we would be remiss without mentioning. The biggest issues are the time it takes to break in the boot. It is a process, and there have been some individuals that report it taking several weeks before the boots are comfortable enough to wear for extended periods.

On top of that, the boots do fit a bit narrowly. This seems to be just initially, and once you have broken them in, they loosen a little in width.


  • The boot is crafted with high-quality material that gives it an extended life
  • Once the boots are broken in, they are super comfortable
  • The design of the boot is not only functional but stylish too
  • Every part of the boot is made with durable materials that can stand up to anything
  • It comes with two pairs of laces


  • Issues with sizing – the boot has a narrow fit
  • Breaking in the boot takes some time

Red Wing Men's 6668 Steel Toe Brown/Black Boot

This next work boot is designed to look like and feel like a hiking boot. It is crafted with everything you want in a work boot but just made with lighter materials for improved comfort.


This Red Wing model looks more like a sneaker or a hiking boot, but it is designed like this for a reason. It is a lightweight option that brings with it the following features:

  • Crafted with waterproof full-grain leather
  • Lining made to wick moisture
  • Molded shank (TC -Tech plate) for torsion control
  • Designed with an extensity outsole for enhanced resistance to abrasion, slip, and oil
  • Built-in steel toe
  • Constructed to be resistant to electrical hazards
  • Safety rating – ASTM F2413-11

No need to break them in! This is one of the best things about this model on our list. Most Red Wing boots come with a serious process to break in, but with these lightweight boots, there is no need to worry about that. The boot still comes with all the other things people have loved about Red Wing boots like durability and quality materials. A lot of the amazing design features and a competitive price make this boot a great investment for any worker.

There one some drawback though that we should discuss so that you can make an informed decision. Like with most Red Wing boots, the fit is narrow. Once you have worn it for a bit, the boot will loosen, but it still fits a little narrow. If you have wide feet, this may not be a good choice for you.

The other issues are that it claims to be waterproof, but there have been some reports of the boot being less than adequate in its protection.


  • Boots don’t have the typical break-in period of other Red Wing boots
  • Crafted with durable, premium-grade materials
  • Designed to be lightweight and comfortable
  • The work boot offers great support
  • Price versus value far outshines most of its competitors


  • Sizing issues – May want to go down a size as they become loose once broken in
  • Concerns over water resistance quality

Red Wing Men's Heritage Work Chukka Boot

Our next entry is a casually designed work boot that can easily go from day to night. Its chukka design makes it great for any event.


If you are looking for a nice looking work boot that can bridge work and play, then some things have to be adjusted a little. This Chukka from Red Wing does this by including the following features:

  • Constructed with a high-quality Atlas tread rubber sole
  • Shaft measurement – 4” from arch
  • Heel measurement – 1”

These Chukka boots are amazing and bring so much to the table, both stylistically and functionally. Of the many things that are great about this boot, the inner lining is probably the best aspect. Not only is it designed completely of leather, which allows for comfortable wear, but it is also created to fit each individual’s feet perfectly.

It also is crafted to wick away the moisture. Then when you look at the comfort with the durability of the design and the materials, you soon see why we chose this Chukka to be one of our choices.

Though there are a lot of great aspects when you look at this boot, there are still a few issues that might cause some to reconsider making this their go-to work boot. The first is, of course, the fit.

As we have discussed with the previous boot, Red Wing boots tend to be a bit narrow. The biggest issue though is that the inner sole offers almost no support, which will affect the stabilization of the boot.


  • You can choose between leather or suede uppers
  • The lining of the footbed is made of leather for a more comfortable and customized fit
  • The inner lining is designed for climate control, which keeps your foot dry and cool
  • Crafted with contrast stitching, which makes the boot look nice
  • Sole of the boot is durable and wears well


  • There is almost no inner sole support
  • Sizing issue – Boot fits narrow until broken in

Red Wing Men's Steel Toe Logger Work Boots

The next boot is a higher ankle boot that gives the worker extra support and still is fitted with all the high-quality features as the rest of the Red Wings on our list.


These logger boots are crafted using high-quality materials and the following features:

  • Built with a Goodyear welt platform to enhance stability
  • Sole is a Vibram lug for better traction
  • Designed with Red Wing waterproofing
  • Offers protection against electrical hazards
  • Built-in steel toe for extra protection

If you are someone who needs a little extra ankle support, then the Men’s Logger could be the answer to all your prayers. It is constructed using high-quality materials and a design that is aimed at making your workday more comfortable.

On top of that, the sole is designed for superior traction, which heightens the safety of this boot. All that combined makes this a great choice for anyone looking for a boot to wear on long workdays.

Some features could be improved on, however. The biggest issue is with the lining quality. There are several reports of the lining coming out or ripping after very little use. This is not a universal issue, but there are enough complaints that we felt we should mention it.

The only other concern is that the toe isn’t reinforced as much as we think would be beneficial.


  • High-quality materials used in construction for longer life
  • The design of the boot is comfortable for long hours
  • Boots offer good ankle support
  • Sole is crafted to give the wearer good traction
  • It comes with a nice lifetime warranty on laces and tune-ups


  • Issues with the quality of the interior lining
  • Could be better reinforced in the toe

Red Wing Heritage Men's Iron Ranger Work Boot

Our last entry is the Iron Ranger, which is one of the most popular models from Red Wing. It is crafted with care and designed to be used in the most intense environments.


This work boot is one of the best because it takes standard features and elevates them to new levels. In order to do that, the Iron Ranger comes with the following features included in the design:

  • Manufactured with a premium grade rubber sole
  • The lining is a soft leather that wicks moisture for dryer wear
  • Crafted with an all-leather footbed for a customized fit
  • Triple stitched welt construction for durability
  • Outsole made with Nitrile cork for better grip
  • Designed with a high-quality full-grain leather upper
  • Cap toe is reinforced for added protection

The Iron Ranger is easily one of the best work boots manufacturers by Red Wing. It is handcrafted using the finest leather and materials. Every detail of this boot is crafted to make the work environment comfortable and safe.

That includes the inclusion of oil resistance as well as the stitch down design of the welt. Everything about this boot comes together perfectly, and that is why it is one of the boots we chose for this list.

Now even though the Iron Ranger is one of the best, that doesn’t mean that there are not a few areas that could stand a little tweak. The boot, like all Red Wing boots, takes a little while to break in, and that can be frustrating and painful.

The toe is also a little soft and doesn’t stand up well to abrasions, which will detract from the look and affect the integrity of the durability of the boot.


  • The boot is designed well and handcrafted
  • The soles are water and oil resistant for rough use
  • The boot is made using premium grade materials for longer life
  • Designed with a stitch-down welt construction for more durability
  • The toe box is a nice size, which makes it more comfortable


  • Boot takes a while to break-in
  • Toe is a little soft and is scratched easily


Red Wing has many different models to choose from, but these five are some of the best Red Wing work boots available. Choosing the right pair of work boots is an individual choice, but hopefully, with the options above, you have a better idea of what you are looking for. You want a pair of shoes that are comfortable but still gives you all the protection you need.

Red Wing offers boots that are specifically designed to guard you against things like slips, electrical hazards, or other potentially dangerous events in the workplace, and they do it in style. Many of the work boots we discussed above are both functional and fashionable, which makes them quite the investment.

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