The 9 Best Red Wing Boots for Men

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Even a city dweller like me understands why guys would want to find the best Red Wing shoes and boots: 

Long known for offering classic boots that blend exceptional quality with enviable personal style, the Red Wing brand has been making quality footwear for decades. 

Red-Wing-Shoes-Logo

Founded by Charles Beckman in 1905, the Red Wing shoe company first came to prominence by making boots for American soldiers fighting in World War I. 

(And continued supplying the United States government all the way through WWII.) 

Since then they’ve expanded the quantity of their offerings while continuing to focus on the important factors that make their boots such high quality, including premium leathers and goodyear welt construction and comfortable leather insoles.

To help you choose the right pair of Red Wing boots to suit your style and needs, in this post we’ve rounded up some of the best boots they have to offer. 

A (Quick) Note on Our (Sharp) Selections: 
Legs and feet of two people wearing Red Wing Heritage boots

Each of the boots below comes from the Red Wing heritage collection, as opposed to their work collection. 

Of course, Red Wing also makes some of the best work boots for construction workers, factory workers, and other hands-on jobs. 

But our goal here is to help you find a great everyday boot that works damn near anywhere, not just on the job site. 

So we’ve focused on heritage offerings because they’re the more style-focused Red Wing collection, and will work best with casual wear. 

And a (Helpful) Heads-Up on Breaking ‘Em In: 
Man inspecting leather Red Wing boot

If you’re look for your first pair of Red Wings, be warned: 

Each model below is a high-quality boot made of genuinely tough leather, and as such they take a little bit to break in. 

The exact amount of time will vary based on your usage, and you might even find that they’re actually pretty comfortable the very first time you wear them.   

But you’ll likely find that they get a lot more comfortable as time goes on. 

You’ll know your new boots are fully broken in when they provide a snug fit that feels like it was custom-made for your foot. 

Look Sharp in Sh*t Kickers:

The (Absolute) Best RedWing Boots for Men 

Overall Best Red Wing Boots ↓

Red Wing Iron Ranger 6” Boot

Red Wing Iron Ranger boots
Rating: 
  • 4.6 Stars
    • 2,368 Reviews
Advantages:

The Red Wing Heritage Iron Ranger easily tops our list of best picks because it perfectly balances the ruggedness that Red Wing is known for with a timeless, classic look. 

On the ruggedness front, the Iron Rangers have the goodyear welt and full-grain leather you’d expect from a proudly American-made pair of boots. 

(Both of which provide a fair degree of water resistance that will help them last a damn long time. I’ve had mine for more than a decade and they’ve held up incredibly, even after plenty of wear and tear.) 

On the style front, they’re available in five different colors and boast a handsome cap toe that helps elevate them over other popular styles. 

In addition to the toe cap, they also have a minimal tread design that lends a certain sleekness, and helps distinguish them from the sort of chunky steel toe work boots you see on construction sites. 

Promising Review: 

After walking a year in these boots, I felt obligated to write a review. I ordered a full size smaller than what I typically wear and, after breaking them over a few months, they feel like they were custom made for me. 

These Red Wings are nice enough to wear in an office environment with jeans, but strong enough to wear over a bed of nails. I’ve put them to the test in all types of terrain and they never cease to amaze me. 

The Iron Rangers were built for miners and I’ve worn mine through mud, snow, rocks and water. After a cleaning and some mink oil, they look better than new because of the patina. 

These will last me my lifetime and are now the only boots I wear when I travel outdoors. Get yours.

Shawn

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Best Red Wing Work Boots (in the Heritage Collection) ↓

Heritage Men’s Classic 6” Moc Toe Boot

Heritage Men's Classic 6” Moc Toe Boot
Rating: 
  • 4.6 Stars
    • 1,912 Reviews
Advantages:

Boasting Red Wing’s traction tred outsole, this is arguably the best Red Wing heritage boot for guys who spend all day on a concrete surface. 

To be clear, if your job requires you to wear reinforced steel toe boots, then these admittedly aren’t for you.

(Though you may want to look at Irish Setter Boots, which is a sub-brand owned by Red Wing.) 

But for those who are freed from (necessary, if style-stifling) safety codes, this a great boot for straddling the line between work and play. 

They’re made from the same type of leather upper as the Iron Rangers above, but the wedge sole offers longer-lasting comfort. 

As a result, they’re more durable work boots than any of the other heritage boots, particularly if you spend all day standing on a hard surface, but still offer a high degree of style.

Promising Review: 

I’m a general contractor. On my feet all day in rough terrain, on concrete, climbing ladders, crawling on my knees. I abuse the hell out of them. These boots flat out rock. 

Not only are they beautiful, that are rugged and comfortable (once they are properly broken in.)

Jered Sprague

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Heritage Men’s Work Chukka

Heritage Men's Work Chukka
Rating: 
  • 4.4 Stars
    • 426 Reviews
Advantages:

Probably the sharpest-looking pair of shoes on this list, the Work chukka definitely isn’t as refined as a dress boot, but might actually be a better option if you mostly find yourself in casual situations.  

With a wedge heel that’s similar to the previous model, the Work chukka offers plenty of comfort, making it another great option for guys who work on their feet all day. 

But chukkas are also one of the best casual boots to wear with jeans, which means they can do just as well on a first date or social outing as they do on the job site. 

Promising Review: 

I’ve had lots of pairs of shoes and boots in my nearly 40 years of life. These are the best boot I’ve ever owned. 

They’re comfortable, stylish, and rugged. I live in the mountains of Western Washington, and I wear these boots EVERYWHERE. 

The ClausMan

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Heritage Men’s Blacksmith Vibram

Heritage Men's Blacksmith Vibram
Rating: 
  • 4.5 Stars
    • 401 Reviews
Advantages:

Similar in style to the Iron Ranger (but without the cap toe), the Blacksmith is another tough boot that can be worn in a wide variety of jobs and social situations. 

Unlike the Iron Ranger, it has what the boot brand calls a “mini-lug” outsole, meaning that the sole has a bit of tread on the bottom, but not so much that it can be seen from the sides.

This makes it even better for working conditions that require a bit of grip, but still allow you to get away with soft toe shoes. 

But it also helps the boot maintain a sleeker profile than the true work boots you’d get from a brand like Thorogood Boots, whose thicker lug sole makes them look too industrial to wear for a night on the town. 

Promising Review: 

Another fantastic boot from Red Wing. The Briar Oil Slick has some slight reddish hues to it, and has a slight texture in the ankle area. 

These work great with chinos or jeans, and I wear them to a business casual office often.

Keegan

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877 8-inch Classic Moc Toe

877 8-inch Classic Moc Toe
Rating: 
  • 4.5 Stars
    • 106 Reviews
Advantages:

This version of the moc toe is similar to the one above, but the leather upper is two inches taller, and reaches higher up the ankle. 

Some guys find that the increased ankle support gives them the best results in terms of stability and comfort, particularly if they spend all day on their feet and want boots that fit as snugly as possible.  

Another thing worth noting about the moc toe is that it’s made from Red Wing’s No. 23 last. 

It’s designed with extra room in both the forefoot and instep, so it may be the best choice for people with wider feet. 

Promising Review: 

The 877 is a high quality boot and meets all my expectations for Red Wing boots… 

Been wanting a pair of 877 for years and I am very pleased. Pliable leather yet durable, classic styling, and pretty much immediate comfort after breaking in the tongue in the fold over technique.

– jrv12

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Classic Chelsea

Classic Chelsea
Rating: 
  • 4.4 Stars
    • 41 Reviews
Advantages:

Built for comfort and convenience, the classic Chelsea is both a no-nonsense and no-laces boot that can take you just about anywhere. 

It has the same traction ted outsole as the moc toe, but the pull-on style of the Chelsea makes it a lot quicker and easier to get the boot on and off. 

Promising Review: 

Great boots. Gets more comfortable and easier to wear as you go along with it.

GT

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Heritage Rover

Heritage Rover
Rating: 
  • 4.4 Stars
    • 91 Reviews
Advantages:

The Rover is similar in style to the Blacksmith model listed above, but has a lightweight crepe sole instead of the mini-lug. 

The result is a boot that’s probably more comfortable if you’re on your feet all day, but doesn’t provide quite as much grip. 

This is a great boot for those who want something to pound the pavement in, but if you’re looking for boots you can wear hiking or in other rough conditions, I’d go with the Blacksmiths. 

Promising Review: 

These are by far the best fitting, versatile and comfortable boots I’ve worn in a very long time… 

Purchase the designated oil for this boot and you’ll never want to take them off.

– Amazon Customer

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Weekender Chelsea

Red Wing Weekender Chelsea
Rating: 
  • 4.5 Stars
    • 53 Reviews
Advantages:

As its name implies, the Weekender is geared more toward casual and social settings than hard-working job sites. 

It has a slightly sleeker toe shape than the Classic Chelsea above, which makes it a better choice if you’re looking for a hardy and well-made boot that will look sharp when you’re off duty.

Promising Review: 

They fit snug as expected, but comfy and light right out of the box. best slip on boot I’ve ever worn. Buying them in black next.

Bryce

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Sawmill 6-Inch Boots

Red Wing Sawmill boots
Rating: 
  • 4.8 Stars
    • 24 Reviews
Advantages:

Easily the best Red Wing boot for cold weather, the Sawmill has everything you need to get through the winter. 

It’s got a ​​felt-wool footbed designed to keep your feet warm in cold conditions, and Red Wing’s hardy Vibram® TC-4 Plus outsole, which provides plenty of traction and grip for snowy, icy days. 

Promising Review: 

I wear these all day. The longer they are on my feet the better my feet feel. Incredibly well made. Very comfortable.

– Stevex

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Bonus!
The Best Oil for Red Wing Boots  ↓

Red Wing Heritage All Natural Boot Oil

Red Wing Heritage All Natural Boot Oil
Rating: 
  • 4.6 Stars
    • 266 Reviews
Advantages:

One of the best things about Red Wings is that they can last forever

But the catch is that you have to take care of them properly. 

Fortunately, caring for them is as easy as cleaning them semi-regularly and applying some boot oil, which adds a layer of protection and helps maintain the patina that makes high-quality leather boots look so damn good in the first place. 

Two words of caution though: 

First, a little goes a long way. Dab a tiny amount onto a cloth and rub it into the boot leather, then decide whether or not you want to add a little more. 

Second, in most cases using oil will darken the color of the boot. 

In a lot of cases that’s ok, since the darker color helps hide some of the scuffs that naturally occur over time, helping the boots look new again. 

But it’s another reason to start small and only use a little at a time, so that the effects on the color are minimal. 

Promising Review: 

This redwing boot oil is excellent for preserving leather. 

I have boots from high school that I still wear today (20 years later) because this oil preserves the soft leather so well.

Alfred Waters

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More Advice on Men’s Boots and Shoes from Irreverent Gent:

The Recap ↓

Overall Best Red Wing Boots

Dave Bowden

Summary

The Red Wing Heritage Iron Ranger easily tops our list of best picks because it perfectly balances the ruggedness that Red Wing is known for with a timeless, classic look. 

4.5

📷
Banner image: Red Wing; Illustration: Irreverent Gent

About

Dave is a men's style blogger whose insightful (and of course, irreverent) advice on how to look good and live well is read by more than two million people each year.

When not obsessing over style and self-improvement, he can usually be found at home playing with his wife and son, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.