Reviewed: Red Wing Work Chukka 3137- What You Need To Know

Are you like me? Do you ever get something in your head and you can’t get it out? It happens to me from time to time and this time I wanted a new pair of boots. But not just any pair of boots. I wanted a great pair of boots that would hold up and look better with age. I wanted a pair that would last. After reading hundreds of reviews and articles, I kept coming back to the Red Wing Work Chukka 3137.

I’ve had these boots for over a year and feel that I’ve worn them enough to give you a thorough review.

Here goes.

Red Wing Work Chukka 3137 Copper Rought and Tough

Who Is Red Wing Shoes?

Red Wing Shoes is an American-made shoe company that’s been around since 1905.

Charles Beckman found it in Red Wing, Minnesota, to make work boots.

Even over 100 years ago, Red Wing’s quality and craftsmanship set it apart.

They produced boots for soldiers in World War I and World War II.

In 2007, they launched their Heritage Brand Boots, which is the line that the Work Chukka falls under.

Red Wing Work Chukka

What Are Red Wing Heritage Boots?

Red Wing Heritage boots came about with a little help from Red Wing boot lovers in Europe and Japan.

As styles changed, people in those countries began wearing the old Red Wing work boots as not as they were intended but as a fashion statement.

They rocked old work boots because they loved the look and feel.

Decades later in 2007, Red Wing Shoes partnered with J. Crew on a collaboration that was so popular that Red Wing developed the Heritage Boots line that features styles for men and women.

Red Wing Work Chukka 3137 Construction

The first thing to understand when you buy these boots is that it’s an investment.

The price can be very prohibitive. But with that price comes a high-quality pair of boots.

Let’s talk about the rugged construction and materials that go into the Red Wings Work Chukka 3137.

The first thing you notice is the leather.

The leather on these boots comes from the S.B. Foot Tanning Company.

They’ve been making high-quality leather since 1872. You don’t stay in business for nearly 150 years by not making quality goods.

The leather is all hand-cut by craftsmen with decades of experience. The reason this is important is since no two cows are the same, no two cowhides are the same.

You need someone with a trained eye to make sure they are using the best sections of leather for your boots.

Although the shoes can get scuffed up throughout the day, it’s no problem to clean them up and leave them looking good as new.

They are unlined, which is perfect for me in Texas, but may not fit your needs if you live in a colder climate. I can get by wearing these most months.

They hold up great in rain and dirt and mud.

The leather sits on a base of Goodyear Welt polyurethane outsole.

The boot is resoleable and comes with nickel eyelets for the laces.

Red Wings Work Chukka (3137) Copper Rough and Tough with blue denim

Why I Chose The Red Wing Work Chukka 3137 In Copper Rough and Tough

When I was first looking at boots, I thought I wanted a Red Wing Moc Boot or the Iron Ranger model. Those are the first ones I saw and they are great-looking boots. No doubt.

But the more I researched them, the more my eyes kept coming back to the Work Chukka 3137 in Copper Rough and Tough.

By the way, the model number 3137 refers to the Copper Rough and Tough leather.

I loved the look of the leather. Still do. It’s a fantastic shade.

I had always been a fan of chukkas. They work great paired jeans or chinos. You can throw them on most any time and not feel out of place.

But these boots aren’t what I would consider a traditional chukka boot like, say, the popular Clark’s Desert Chukka.

Don’t let the laid back style fool you. These boots can handle plenty of work.

That’s what makes them more flexible.

They would work in the outdoors or casual office environment or dressed up for dinner and a movie.

The contrast of the leather with the white outsole was just another bonus.

They are handsome boots.

Red Wings Work Chukka Copper Rough and Tough review

Red Wing 3137 Work Chukka Fit And Feel

Like I mentioned earlier, these boots fall under Red Wing Heritage line of boots. What that means is that they are more designed with a nod to lifestyle and looking great than hard work.

But don’t let that fool you. These Work Chukkas will hold up to plenty of work.

Don’t baby them. They’re boots, after all. They’ll respond.

The first thing I noticed about these shoes is the quality of the materials.

The leather is first-rate, soft, and durable. And like quality leather, it will look even better with time.

What makes them so great is that you can throw them on in the morning for some yard work and them clean them off in time for date night.

What about comfort you ask?

Well, here’s the rub. Maybe literally.

They aren’t easy to break in. Far from it.

I had read the reviews about how they took some people 2 months to break in. So I knew what I was getting in to.

Let me just say they were absolutely spot on.

In my experience, the leather only took about 2 weeks to break-in. I expected that and overall was were with that timeframe.

The soles were another issue altogether.

They took every bit of 2 months to feel comfortable on my feet.

There was a lot of taking my dog walking with my dogs barking.

But over time, they broke in and became softer and softer.

It just takes some time, so be prepared.

I just kept telling myself that I bought these boots to last years and years. I can handle a couple of months of them being less than ideal.

They handle well in wet and sometimes icy conditions.

As far as sizing goes, I’m a 10 medium in Nikes and Vans and I was a 9.5 in these. So keep that in mind.


I wear these boots nearly every day in the Fall and Winter and I love them more and more as time goes by.

Your enjoyment of the Red Wing Work Chukka 3137 will come down to how much discomfort you can manage while breaking them in.

If you can tough it out for a while, this is a simple decision because once they’re broken in you’re going to love them.

The leather and construction are top-notch. The craftsmanship is absolutely what you want in boots at this price point.

I can’t recommend them highly enough. I can’t wait to wear them again when the weather cools off.


Are The Red Wing Work Chukka Comfortable?

No, and yes. At first, they are stiff on your feet and may take some time to break in. However, once broken in, they are extremely comfortable to wear all day. These aren’t sneakers. They’re handcrafted leather boots, so set your expectations accordingly.

What Are Chukka Boots Good For?

One reason chukka boots are so popular is because they are incredibly versatile. You can wear them to with chinos or jeans. You can dress them down or up so they work in an office environment.. Plus, they are rugged and sturdy enough for physical labor.

How Do Red Wing Work Chukka 3137 Boots Fit?

I really recommend going to a Red Wing store and trying these on before you buy. I’m a normal size 10 in sneakers and dress shoes, but I was a 9.5 in these boots. So it’s mostly true to size, but it’s always better to try before you buy just to make sure.

If you’ve got any questions, let me know in the comments.

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