A Guide to Work Boots (featuring Red Wing 877)

This next boot break-out from my Fall and Winter Boots post is all about the tough guy of the group, the work boot.

Defining Work Boots

This class of footwear has two major jobs: to protect your feet and ankles and to stand up to harsh environments for at least 8 hours.

We could arguably add a third, which would be to look badass, but that's really just a side effect of accomplishing the first two.

These boots come from manufacturers that will probably sound familiar – Red Wing, Wolverine, Chippewa, and Danner.

They're different from your mall brand knockoffs, which may look similar but don't be fooled.

With cheap imitations, the linings will wear prematurely, the soles won't last more than a season, and the pleather uppers will crack (not to mention look cheap and make your feet sweat).

As far as material is concerned, you'll usually find work boots to be constructed of tough, oily leather (as opposed to the thin, smooth leather of dress shoes).

You won't find a sleek silhouette, decorative stitching, or elaborate perforations here.

Without the need to look elegant, work boots can be as chunky as required to be practical. You'll almost always see these with a rubber sole, and more often than not they'll be lugged.

Now I'd like to turn the focus to my work boot of choice, the Red Wing 877.

History of the 877

Introduced in 1952 as a sport/hunting boot, the Red Wing 877 soon outgrew its target audience.

The oil tanned uppers were reasonably water resistant so they naturally appealed to anyone spending a significant amount of time outdoors, like farmers and construction workers.

The crepe soles have a very unique tread pattern. Instead of having massive lugs common on boots of this type, Red Wing utilized a more mild tread pattern.

Traditional heavy lug soles tend to become caked with mud and snow and, as a result, become very heavy and lose their ability to grip the environment.

This sole is part of what attracted the farmers and ironworkers. With no protruding lugs to collect mud or snag on a bolt while 40 stories in the air (yikes!), these boots were a natural fit for all kinds of work environments.

My Experience

“What did I do to deserve this?!”

That was all I could think while wearing these boots during the first month.

They truly are painful to break in, as most things built to last are (i.e., raw denim, leather work gloves, etc.). This is something we're not accustomed to in today's throw-away society.

The truth is that these boots are not a fashion accessory designed to last this season and then be replaced by the newest trend the next.

They're meant to stand up to the rigors of the countryside and construction sites. The cushy lightweight options simply aren't up to the task.

When you first buy these boots, the leather insole is hard, the leather uppers are stiff, and the unlined interior is anything but a hospitable environment for your foot.

But over time, maybe a month or two, they begin to break in.

Your foot molds the foot bed to your exact specifications, the uppers become flexible wherever there is movement, and remains rigid where there isn’t.

Soon, you have a custom-made boot that is sure to last as long as you care to keep them.

Break-in Tips

Wear them around the house, even if you aren’t walking much. The heat from your foot will help mold the leather footbed.

Applying some oil can help speed the process. I used Red Wing all natural boot oil made with pine pitch and mink oil.

Smells amazing! Really, I pick up these boots and smell them whenever I walk by. Weird, but true.

You can also crouch down on your toes with bent knees while watch TV or messing around on the computer. The key is to flex the toes and ankles.

This helps to soften up the two major points of movement. I found this to be the most helpful break-in accelerator.

And of course, the old tried and true method of wearing thick socks for the first few months will help ease the pain.

How to Wear

No doubt, these go great with jeans. They give you that tough guy, cafe racer look that’s hard to beat (PBR optional).




They can also be dressed up (to a certain extent). Though it's unlikely you'll be able to wear them to the office, you can achieve a more dressy look by pairing them with heavier fabrics and patterns.

Think: old money out hunting pheasant in a tweed suit. Gentleman Hunter, if you will.




Work Boot Options

Though I'm a big fan of the Red Wing 877, there are a number of great work boot options. Given that good work boots usually cost in the $200 to $300-ish range, this list doesn't really present substantially different price points.

Here are some of my favorites.

Chippewa Apache

Red Wing 877

Wolverine 1000 Mile

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  • Reply
    March 3, 2015 at 1:28 am

    I’m looking forward to grabbing a pair of these bad boys. It’s high time I stop sporting tennis shoes so often and get a little distinguished before I turn 40!

    • Reply
      March 3, 2015 at 2:37 am

      Nice choice! They’re well worth the investment. I’ve had mine about five years and aside from some surface scuffs, they’re as solid as the day I opened the box. If you haven’t already, check out my guide to desert boots. I think those are a great replacement for tennis shoes, also.

  • Reply
    July 17, 2015 at 8:24 pm

    What are your thoughts on the 877 versus the Nordstrom exclusive Redwing Moc Toe boot? I want a good Winter boot and keep waffling on these. I live in the DC area so not a ton of snow but these could be useful for yard work and when we do have some inclement weather. Although I’m also guessing I should get some duck boots too.

    • Reply
      July 17, 2015 at 11:45 pm

      The Red Wing made exclusively for Nordstrom seems to be almost identical to the 875 (just a few eyelets shorter than the 877). I think you’d do just fine with either, although, the model from Nordstrom is significantly cheaper.

      The Red Wings do a good job in light snow, although they don’t have tons of traction and water will eventually soak through. Unless you go full on dedicated snow boots, some sacrifices will have to be made.

      Good luck and buy which ever ones speak to you most. Enjoy!

  • Reply
    November 13, 2015 at 12:09 am

    I like your site Nate. It fills a niche.

    I really like Red Wing. I’m looking for an excuse to give them more of my money. I’ve had a pair of Red Wing 8111s for three years now. Traction in snow is non-existant but I live dangerously. With a good dash of oil every now and then they look better than when they were new. The only issue with the hard rubber sole is that people always hear me coming!

    Less stoked on Danner. Was not pleased when the stitching started to come apart in the field. “$500 and this happens NOW? And it’s starting to snow. Fuuuuuck.”

    • Reply
      November 14, 2015 at 6:00 pm

      Thanks Aaron! I’m with you on the Red Wing love. I plan on getting a pair of the 8111s one day. I also really like the Beckman. That sucks to hear that your Danners failed you. I had a pair of military spec boots from them that were awesome. I gave them back to my buddy because they didn’t have a place in my wardrobe, but I’m regretting that now.

  • Reply
    December 28, 2015 at 10:19 pm

    I got the 877s and I’m wanting to know wether it’s a style boot or if I can wear this for labor ?? Thanks .

    • Reply
      December 29, 2015 at 7:01 am

      It’s main purpose is undeniably labor. It just so happens that it looks great and has become increasingly popular as a casual style boot in recent years. Don’t be afraid to beat on them!

      • Reply
        January 1, 2016 at 1:35 pm

        Yeah I’m in the process of breaking them in , they suck right now but once I’ve broken them in ill be super excited , very comfy and feels like spider man boots or some 💩 on the real if you guys want some good fit boots that mold perfect , I say get the redwing 877 . I appreciate this , it really helped thanks @NATE . Keep up the good work .

  • Reply
    Robert Saunders
    February 11, 2016 at 7:46 pm

    I’m on my third day of breaking in my pair of 877’s and im having the usual sore feet and arch ache that is associated with breaking in a pair of red wings. However this is my first pair of 8″ work boots and I’m worried the extra length is bothering my Achilles and ankle. After about 4 hours of wear at work the back of my heel about 5 inches up (I’m guessing my Achilles) aches. After taking them off and switching to a broken in pair of red wings they feel weak and unstable. I was wondering if this was normal or to be expected prior to breaking in the leather? Thanks!

    • Reply
      February 12, 2016 at 9:27 am

      Is it right where the boot flexes in the back? I had a similar issue. The leather is double thick in that area and when it bends it can push pretty hard into your lower calf area. You could try working the leather by hand while you watch tv at night. I would suggest wearing them for shorter periods at first to minimize pain. You’ll have these boots for years so there’s no need to rush things. One more tip, although it won’t hasten the break-in process, is to skip a few eyelets opposite the pain point. This’ll make the boots fit looser in that area. They’ll be worth it in the end so hang in there!

      • Reply
        Robert Saunders
        February 12, 2016 at 11:14 am

        What was your issue? Did you only have this pain with boots this height? And yes when I flex my foot forward the leather about 3-4 inches above the sole flexes inward and pushes into my lower calf. Do you think the extra stiff leather and added height of these 8″ boots are making the back of my leg tired? I figured once I break them in and the leather flexes in all the right spots this pain will subside. At least that’s what I’m hoping. Thanks for the reply!

        • Reply
          February 12, 2016 at 12:15 pm

          I had the same pressure around my Achilles tendon, but it eased up over time. That’s just the nature of these boots, softer leather just doesn’t last as long. I always wear tall boots but this was the first pair that caused that. I don’t think it’s the height because most guys actually report more pain with the shorter 875 boot because it cuts in at that spot, rather than pressing. What type of boots are you comparing them to?

          • Robert Saunders
            February 12, 2016 at 4:19 pm

            I have a pair of 6 thorogoods and 6″ red wing 1907. On my 1907 I never felt that pain in my Achilles but I did notice the overall height of those boots to shrink as they broke in which is why I I got the 10877 for work. I managed to wear them today fit about 7 hours before it was too uncomfortable. How long did it take for that Achilles pain to subside?
            I tried tying my boots lower but the pain is the same. I’ll work on them tonight or something like you said.

          • Nate
            February 13, 2016 at 5:19 pm

            Hmm, those are pretty good comparisons. I was asking just in case you were comparing them to something really soft like Timberlands. If I remember correctly, it took a few weeks for the boots to be completely broken in.

  • Reply
    March 16, 2016 at 10:45 pm

    Hi Nate,

    I was curious about your opinion regarding moc-toe vs plain toed boots. If you were to only have one do you find that one is more versatile or is it totally a matter of opinion? And if that the case given your experience, what’s your opinion?

    Thank you.

  • Reply
    November 2, 2016 at 7:27 am

    What cardigan are you wearing? The fit looks great!

  • Reply
    December 14, 2016 at 6:06 am

    Hey! I have a small dilemma going on with my Red Wing boots (8830), I wanted to see if you could share some insight in any way.
    I bought these awesome pair of boots around August, broke them in and everything. I use them for work (8-10 hour shifts) every day. About two months ago, though, they attained this weird kind of smell; a smoked-leather type of scent. It isn’t noticeable, nor does it intervene with my feet, but I wouldn’t like for my amazing boots to smell that way.
    Do you know of anything that can help me get rid of the smell?
    Thank you, in advance.

    Awesome article, by the way! The simple fact that one owns a pair of these boots, is enough to entitle one as a badass.

    • Reply
      December 14, 2016 at 1:57 pm

      I’ve never had that with my Red Wings. Is the smell on the inside or the outside? If it’s on the inside, I’d say to get some cedar shoe trees and leave them in for a few days. If it’s on the outside, get some Red Wing Boot oil. It’s made with pine pitch and has an incredible pine scent.

  • Reply
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