As of recently, I've gone from having a sneaker collection to having only high-quality boots. It first started when I got into raw denim and I haven’t looked back. The leather boots I own look better with more wear, as opposed to sneakers looking worse the more worn in they are. The Red Wing Heritage Work Chukka Boot is no exception. Here are a few of my thoughts on the unique and must-have Red Wing 3140.
When I first ordered this particular red wing boot, I wasn’t too crazy about them. Something about how the laces looked matched with the thickness of the sole didn’t rub me the right way. I was used to chukka boots looking more like desert boots ala Clarks. So needless to say these were different. Alas, I bit the bullet and ordered a pair from Amazon to try out for a few days to see if I liked them. And, you guessed it, I loved them.
When I first pulled the Red Wing Heritage 3140 from the box - they’re the Briar Oil Slick color, by the way - all of my preconceived notions went out the window. These red wing chukka boots do have a bit of weight to them but nothing out of the ordinary when it comes to red wing shoes.
At first glance, and as I’ve worn them, I don’t recommend them as work boots per say, but are a perfect pair of oil tanned boots built with goodyear welt construction. They look great with any wash of selvedge denim or khakis and, like all oil tanned leather shoes, only look better with time.
Right when I put these on, I knew I was in trouble. But, like, a good kind of trouble. I knew these were an investment as I’d be able to write about them and because they are a great addition to any closet. Having done my research before I purchased these, I wasn’t too worried about the initial break-in period.
Most red wing boots take a while to fit to your feet but these surprisingly didn’t take very long, which was a nice change of pace. The red wing heritage work chukka boot, especially in the briar oil slick color, took about a week of continuous wear to break in.
I’m normally a 9 or 9.5 in Red Wing’s in general - typically one-while size or 1/2 size down from Adidas or Nikes. The red wing chukka boot is my go-to when it comes to going to the office which is nice because they carry a professional air about them, but can be worn during a night out or if you’re bopping around town running errands.
The look of these is different from other chukka boots. As I said earlier, I was expecting more of a Clarks Desert boot vibe and/or look to them. These red wing heritage work chukka boots sit a tad lower than a desert boot - which comes up slightly onto the ankle more.
All of that said, it is nothing catastrophic as far as differences are concerned. What makes me like the look of these more than a Clarks desert boot is the build and premium construction of them. Plus, I’m just a huge fan of red wing boots in general.
Red Wing Boots and quality go hand-in-hand. You know what you’re paying for especially with the premium price tags that red wings come with. I've worn these almost exclusively for the entire two months and not only do they look like new, but have developed a nice leather patina.
I’ve been them through some heavy use, as well. Wearing them to the office, on walks with my dog, out and around the city - regular daily use but a lot of it. I’ve proudly worn these in the rain, mud, and even mowed my grass in them to help them break in as quickly as possible.
Regardless of what I put them through, I know that these red wing chukkas will last a lifetime. Not only because of the high-quality materials and the red wing warranty, but also because of how good they continue to look with time.
What I like: These Red Wing No 3140 chukka boots are amazing and will surely be your go-to once they’re properly broken in. They look great with everything in my wardrobe and are incredibly comfortable as well.
What I don’t like: The typical Red Wing break-in period is annoying, but worth it!