Over the past few years I've grown from only wearing sneakers to a lover of leather shoes. This all started few winters back when I bought a pair of Saint Vacant Derby boots and fell in love with them. I loved how they felt and how, even with all the slosh and mud, you could make them look like new with just a little bit of spit and elbow grease.

Last winter, to adhere to the "never wear the same leather shoes for two days in a row" rule, I wanted to find another pair of shoes. While searching online for high-quality leather shoes, the Red Wing brand kept coming up again and again and again. It seemed that everyone had nothing but great things to say about their shoes.

So when I happened to notice that our local shoemaker and general store Pinkomo was stocking a really nice selection of Red Wing boots, I had to go over and try them on.

I immediately fell in love with the No. 3140 Heritage Work Chukka boots.

Fit

The second I put these on, I knew I wanted them. They fit perfectly and were extremely comfortable to wear. This despite the many warnings online, and from Pinkomo, that these shoes require a long breaking-in period.

So, after I purchased these, and since they felt so comfortable to wear, of course I disregarded all the warnings and took them on a weekend trip to St. Petersburg. As my only shoes.

Big mistake.

As a word of warning: these boots do require a long breaking-in period! It took me a good month or two of wearing these to get them properly worn in. Now, after being properly broken-in, they are the most comfortable shoes I own.

Quality

I really enjoy the quality of my Saint Vacant shoes, but the Red Wings are on a whole new level! I've worn these almost exclusively for the entire past winter and they still look like new. And they've seen some pretty hard use: I've worn them in dog-parks, had my dog scratch them, stand on them and generally do everything you're not supposed to do with nice leather shoes. I've walked in mud, slush, rain, forest and almost every kind of foul weather you see during a typical shitty Finnish winter.

No matter what I've thrown at these shoes, after a year of heavy use they still look like new and they feel like they will be around for many winters to come. Actually, with a proper care, they will be around for decades.

Conclusion

What I like: The Red Wing No 3140 chukka boots look and feel amazing, they are actually one of my most comfortable shoes. They are long lasting and keep looking like new with just a little care and maintenance. No need to buy new winter boots every year.

What I don’t like: Only thing I can think of is that they need a long breaking-in period.