Red Wing 3140 Work Chukka

Disclaimer: I'm not paid to write about this post, this is purely my ownership experience using these boots!

A blog on a pair of shoes?

A bit unusual for my blog that I'm writing about a pair of shoes. It is still just a shoe, but it is a Red Wing Chukka, the 3140 in the Oro-Iginal leather. There is a reason why I'm writing about this piece of hardware that brings joy and comfort to my knee and foot. I have experienced pain in my left knee for days together after walking with my current shoe and trust me, this is no fun. I was in serious need of a pair that is rugged and at the same time easy on my knee. Enter the Red Wing Work Chukka 3140!

Red Wing 3140 Boots 1
Red Wing 3140 Boots 2

I went with this Oro-Iginal leather as I find the color to be more versatile. It should look good in a casual setting and should give me a contrast look when paired with my raw denim pants. I'm not new to Red Wing shoes as I have owned a pair of the that I have been using for a few years until the recent flooding to which I lost it.

Why do I want to write a blog article about this? The main reason being that I have been struggling with my pair of shoes that I have purchased from the local shoe store which is making my knee problems worse. If you scroll through a few posts from the past, you will see that I do not have knee ligaments on my left knee as a result of an MTB accident 2 years ago. Most of the shoes that I have been using are making the problems worse. I needed a pair that is leather enough to last for decades and at the same time is soft to walk long distances. Red Wing Chukkas kind of tick both the boxes for me. It is this combination of the leather, and the tread sole that made me to purchase this pair.

Red Wing 3140 Shoe 1
Red Wing 3140 Shoe 2


You need to be careful with sizing as some Red Wing models like their Moc Toe, or the Iron Ranger runs relatively large primarily because of the last that is being used, but the Work Chukka's use a completely different last which is a bit narrow and long. Here is the rule to size your Red Wing boots. With the Moc Toe and the Iron Ranger, size a full size down from your normal shoe size. With the Work Chukka, go a half size down from your normal shoe size.

In my case, I'm a US 11 on a normal shoe that you get from the ubiquitous shoe store, hence I landed a US size 10.5 on my Chukka. I can wear a think or a thin socks and I have no complaints!

Red Wing 3140 Size


The leather Oil-tanned, meaning that the leather is impregnated with oil during it's construction. It is equivalent to water proofing the leather to a certain degree. Oil-Tanned leather is exceptionally durable, pliable and soft. When new it starts as a bright Orange and as you wear, it gets scuffed and buffed against the environment and evolves a natural patina that kind of darkens it to a certain extent.

If you take proper care of the leather, it should you last you forever.

Red Wing 3140 Leather 1

Red Wing 3140 Leather 2

Comfort & Durability

Nope! It is not comfortable the very first moment you have them on your foot. It takes some taming. Be ready to have some pain, discomfort for the first few days. Thankfully, breaking-in the Work Chukkas is much easier than breaking-in a pair of Moc Toe, or the Iron Ranger. If you get your sizing nailed on, in just a few days time and wear you will have your most comfortable pair of quality leather boots ever.

There are two available widths to choose from, the D or the EE where the latter is a bit narrow compared to the wider EE width. I absolutely have no complaints on the D width. The fit like a glove.

The shoe is 360° Good Year welt, a construction method introduced in the 19th century and still widely used. This construction gives these boots extreme durability.

Red Wing 3140 Welt
Red Wing 3140 Welt

Thankfully, I had a pair of laces lying around which was longer by a few inches. The stock ones that came with the shoe is a bit smaller. I just replaced it with the Moc Toe laces that I had as a spare.

The soles in the Work Chukka is not stitched to the welt like in the Moc Toe, but rather is just glued. The glue has a tendency to come off after a certain period of time. I have seen people complaining of the sloe detaching from the shoe. But this is not an issue as it can be resoled countless number of times (though they incur some cost). There is a possibility to resole this in such a way that it can be stitched to the welt. I will do this once my sole wears out.

Red Wing 3140 Sole

There is a leather inner sole that gets shaped to your foot after a few months of wear. You can literally feel your toe marks after a few months of wear indicating that the shoes are truly yours. It is a bit uncomfortable when you start as your foot has to wrestle against some hard leather, but trust me it gets smooth (just like every other relationship) after few interactions.

A mention on the outer sole which is where the magic for my knee happens. It is super soft that is so very comfortable when walking long distances.

So there it is! The Red Wing 3140 Chukka in Oro-Iginal leather that I can use for decades to come.