Red Wing Work Chukka Boot Review: 8 Years and One Resole

I wanted to share my 8-year review of Red Wing 3141 Chukka boots. I absolutely love these boots, and when I was first looking to buy a pair, I couldn’t find many reviewed that shared a real-world opinion on how they may hold up over time.

The brand’s Weekender Chukka, with its extra lightweight and flexible build, is the more popular option. But it’s more of a comfy leisure boot than a hardwearing, Goodyear welted boot like my 3141s.

When it comes to Red Wing Heritage, I have only tried these Chukkas and the Classic Moc Toes. I’m not a boot expert with a thousand pairs — I just know what I like and want to share what I’m pretty sure is the most long-term review of these boots on the internet.

Red Wing Work Chukka Pros & Cons

How have they held up after nearly eight years of wear? And if you’re thinking about buying a pair, should you? Let’s get into it.

What I like:

• Incredibly Comfortable: They are the most comfortable boots I own and required no break-in period. I’ve never had a single blister.
• Versatile Style: Perfect for wearing around town or to the office. They are certainly easier to wear than their more rugged, work boot-looking footwear.
• Durable & Ages Beautifully: The leather is soft but tough. All the dents, scratches, and creases have added to the character over the years.
• Easily Resoled: This Goodyear welted boot is easier to resole than Red Wing’s other chukka, the Weekender, which has a different construction.
• American Made: I’m British myself, but I know American craftsmanship is highly valued by many boot fans.

Downsides, but not deal breakers:

• Sole Wear: The original Atlas Tred outsole is a little thinner than most work boots; it’s comfy and flexible, but it wears down a little fast.
• Potential Sole Separation: After years of wear, I noticed the welt beginning to separate slightly from the sole in one spot — but this was fixed when they were resoled. Man, it’s great to be able to resole boots.
• Soles Can Stain: The light-colored crepe sole is susceptible to staining. Volcanic ash from a trip to Iceland permanently stained the sides of mine, but hey, it’s a cool story.

How I Tested These

I’ve owned these boots for approximately eight years. I wear them almost every day for commuting and general wear in London. They’ve traveled with me, including a trip to Iceland, where they were worn on black sand beaches.

My Decision: Chukkas vs. Moc Toes

I’ve had these for many years. The color is “Briar Oil Slick,” which is a rich, dark red that darkened with wear to an almost chocolate brown with hints of burgundy. Here’s what it looks like when it’s new, as seen on Nick’s Red Wing Blacksmiths:

When I first decided to get a pair of Red Wings, I walked into the store intending to buy the classic Moc Toes. But the staff explained that for someone who planned to wear their boots around town and to the office in London, the Chukkas were the better choice because of their versatility and comfort.

The Moc Toes look amazing, but they require a significant break-in period and they’re more firmly casual. There’s certainly nothing wrong with a casual boot (they’re our lifeblood here at Stridewise) but if you’re only going to get one boot, there’s a strong case for a chukka over a moc.

How Comfortable Are the Red Wing Chukkas?

• Zero Break-In Period: The Red Wing store staff told me these were their most comfortable shoes, and they were 100% right.
• No Blisters, Ever: I’ve had absolutely no issues or blisters with these boots — your mileage may vary, though!
• Soft, Pliable Leather: The leather is tough, but with wear it became remarkably soft and pliable.

When I was in the Red Wing store, they told me I wouldn’t need to break these in or worry about blisters, and that has been completely true. They are, by far, the most comfortable boots I own. If you’re looking for an entry-level boot, this is definitely a top contender.

It’s a little hard to say why I didn’t have a tough break in, given it’s the same leather upper and Goodyear welt construction of their more blistery boots, but I think the thinner sole has a lot to do with that.

Note that Red Wing’s leathers are oil tanned, meaning they’re chrome tanned and infused with a lot of oils as they’re produced. Chrome tanning, and doing so with a bunch of oil, helps to make a more flexible leather than the less common vegetable tanned leather that some boot fans prefer. No shade to them, but there’s no doubt chrome tanned leather is more comfy from the get go.

Long-Term Durability

• Leather Upper: The leather has held up incredibly well, developing a beautiful patina and creasing without any tears or damage.
• Stitching: All the original stitching, including on the Goodyear welt, has remained intact.
• Original Laces: Even the original laces have held up after almost daily use for years.

After eight years, the boots are holding up exceptionally well. (That’s more than I can say for their wearer!) I only needed to replace the soles recently, but other than the soles wearing thin, nothing has come out of place. The dents and scratches just add to the character. You can see where the bones of my feet have shaped the leather, creating creases that I personally love.

The only real sign of wear, besides the sole, was a spot I noticed where the welt seemed to be coming away from the sole. The stitching was still holding, but it was a clear indication that it was time for a resole. Fortunately, nothing busted before the resole and the resole operation fixed it just fine, so I guess there was nothing to actually complain about.

Construction of Red Wing 3141 Chukka

• Goodyear Welt: This construction makes the boots durable and allows them to be resoled, extending their life.
• Atlas Tred Outsole: The original sole is a comfortable crepe sole called the Atlas Tred.
• Briar Oil Slick Leather: The leather has a beautiful matte finish that develops a wonderful patina over time. It’s also very pliable and soft.

These boots feature a Goodyear welt and an Atlas Tred outsole. I know Vibram makes the Red Wing branded wedge soles you see on their boots, so there’s a decent chance they also make this slightly thinner “Atlas Tred.”

I love the patina everything has developed, from the creases on the tongue and the worn-down edges of the welt.

They are also practically waterproof. You have to be careful with that word because it’s not like you can stand in a lake all day, but I’ve never once had wet socks living in rainy London — so they’re as waterproof as your average guy needs.

The original laces have held up well. The stitching all around the inside is beautiful, and it has started to get worn down and shiny in spots where it rubs the most.

Just note that this isn’t a shiny leather, at least not if you’re just treating it occasionally with mink oil.

Resoling My Red Wing Chukkas

• New Soles: I replaced the original worn-out soles with off-white Vibram Christy cut soles.
• Initial Reaction: The look was very out-there and received mixed reviews; many people said I’d ruined the boots.
• One Year Later: The bright white has aged into a nicer, toned-down color with some staining from mud and wear, making them look much better.

After nearly wearing through my original soles, I took them to a cobbler near my work that had really good reviews. It was also an official Viberg retailer. The resole cost £75, which was much cheaper than other options. I decided to try something different and went with a Vibram Christy cut sole in off-white.

I’ve had a lot of people ask for an update, so check it out: I made two videos on the operation. With some wear, the once-bright soles have aged nicely and don’t stand out as much.

The boots themselves are as lovely as ever. The leather is super supple, and they are still the most comfortable shoes I own. However, I have noticed a couple of minor issues.

On the front of one boot, the new sole is starting to come away a little bit from the shoe, and one of the shoes now makes a little squeak, and I can’t quite pinpoint where it’s coming from. These issues would be the fault of the cobbler, not Red Wing themselves!

Sizing Red Wing’s Work Chukka

• Order a half size down from your Brannock size
• This may be a whole size down from your sneaker size; get your foot measured before ordering

Like most Goodyear welted boots, Red Wing’s Work Chukka runs large: a size 11US fits like an 11.5US. (I’m British, but I’m writing for the Americans reading this.)

Most guys simply don’t know their real shoe size; they’ll parrot their largest sounding sneaker size instead of measuring their foot on a Brannock device. (We all know why guys like to think they have bigger feet than they do.)

Many of my sneakers are a 12, even though my Brannock size is 11.5. Once you know your Brannock, just subtract 0.5 from that number: my Work Chukkas are 11.

Unlike some of Red Wing’s boots, the Work Chukka isn’t currently offered in wide widths. They aren’t narrow boots though, and guys with E or EE width feet might have some luck by sizing up half a size from the recommendation I’m making here.

Red Wing’s Work Chukka vs Weekender Chukka

Red Wing sells two chukkas, the Weekender and the Work, and the differences are similar to the differences between their Weekender and Classic Chelseas.

Basically, Weekender boots are so named because they’re designed for wearing off the clock as opposed to during the workweek: on Weekender boots, the sole is thinner than on work boots and the construction is more lightweight because Weekenders use a kind of stitchdown construction instead of their work boots’ Goodyear welt.

Which should you get? Aesthetically, the eyelets are a little smaller on the Weekender Chukkas and the Work Chukkas have a more structured toe compared to the relatively flat toe of Weekenders.

Beside the look: Weekenders are lighter and more flexible, but the soles are a little less durable and the stitchdown construction means it’ll be a little harder to find a cobbler who can resole them.

Stitchdown boots are resoleable, it’s just not as easy to resole them as Goodyear welts are. Any cobbler will take a Goodyear welt, but he might need some convincing to take on a stitchdown boot.

Price: Are Red Wing’s Work Chukkas Worth It?

• $290 – $300
• Good value for an American made, Goodyear welted boot

Yes, the Red Wing 3141 Chukka boots are absolutely worth it. For their price, you get an incredibly comfortable, durable, and versatile boot that can last for over a decade with proper care and resoling.

Red Wing lives up to their reputation, here: these are the platonic ideal of the longlasting, better-with-age leather boot.

Wrapping Up

That’s a wrap! I hope you found this review useful. If you enjoyed it, feel free to visit my YouTube Channel. Give it a like, and if you haven’t subscribed already, please hit that red button, it really helps me out.

Thanks for reading, and have a great day.