What Type of Jeans to Wear With Boots?

It goes without saying that the best boots should be worn with the best jeans.

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I began with boots, but after experimenting with a wide variety of excellent denim brands, I can now say that I am a denim man.

These are my go-to types of jeans whenever I want to match them up with a pair of high-quality boots.

If you want to know how to pair your boots with different types of denim cuts, here are the six most important types.

It took me a long time to determine the type of denim cut that complements my body shape the most. So let me describe some of the various types of jeans and the types of boots that match best with them.

I’ll tell you which cuts should be avoided based on my personal experience.

Skinny Jeans

Skinny jeans have a pronounced taper below the knee and are narrow through the thigh. This is unquestionably a look that is more appropriate for younger people, and I would never suggest that middle-aged or older guys try to emulate it in any style, shape, or form. The only exception to this is if you are one of those really skinny guys who, regardless of what you do, always manage to exude an air of effortless coolness.

However, there are only 12 of such guys in the world, and it’s quite unlikely that you’re one of them. I’m sorry. I don’t fit that description either.

Skinny jeans look best when paired with low-profile socks like Chelsea boots.

This style has a more rock and roll feel to it. Again, early-twenties males do a pretty good job of pulling that look off. But if you’re over 30 or approaching it, I would simply avoid it.

Slim Tapered Jeans

The sophisticated alternative to skinny jeans for men is a pair of tapered jeans with a slimmer leg opening. Compared to skinny jeans, slim fit jeans offer a little bit more room in the seat and thigh.

However, they remain quite crisp and narrow. Additionally, they taper somewhat below the knee.

I believe that this narrow jean style looks great with narrower, more slender boots. A great illustration is pretty much the entire lineup from Thursday Boot Company.

I find the tapered jean looks great with Thursday boots because of their sleek style.

When paired with a jean that is tapered below the knee, other, bulkier boots, like the Red Wing Iron Ranger, look excessively huge.

Slim Straight Jeans

Although there is no taper below the knee, slim straight is equally narrow and slim through the thigh.

If you don’t have particularly huge thighs but still like to wear bulkier boots like the Redwings or Wolverines, a slim, straight jean is a great option.

I have broad thighs, therefore I personally dislike how slim straight jeans look on me. Because of this, I find that slim straight jeans closely enclose my thighs, yet the lack of a taper gives the impression that I’m donning bellbottoms.

For this reason, I just choose jeans with a straight cut so that I have more room in the seat and in the thighs of the pants.

But that’s just the way my physique is. Guys with thighs of a more normal size could feel as though they are swimming in a pair of straight-cut jeans. A slim straight would be much more appropriate in that case.

Straight Cut Jeans

Jeans with a straight cut are my personal favorites. They are straight all the way down to the leg opening and offer enough of room in the seat and thigh.

I began to wear a lot of boots from companies like Red Wing, Nick’s, Whites, West Company, Truman, and Grant Stone.

At least when compared to a brand like Thursday, all of these boots are a little bit bulkier.

For a more mature look that is more appropriate for guys in their 30s and beyond, pair a thicker, high-quality boot with a pair of straight cut jeans.

And that makes sense, given that most 20-year-olds typically lack the resources to afford a $300 or $400 pair of boots.

Therefore, the smaller, dressier, and more fashionable boots are a better financial decision.

Straight cut jeans still have a pretty tight seat and thigh fit for me. However, they don’t look as tight as a slim fit would.

Because they do not taper below the knee, they fall exactly the same way that a slim straight jean would.

Boot Cut Jeans

Jeans with a boot cut have a slight knee flare. Although I personally don’t wear boot cut jeans, they are the preferred option for cowboy boots.

I also enjoy donning my straight cut jeans with cowboy boots, though. That’s partly due to my individual style. Western-style clothing isn’t really my style; I prefer heritage clothing.

Relaxed Fit Jeans

Another fit I steer clear of is relaxed jeans. I would recommend at the very least going out and trying on a pair of straight cut jeans, even though it’s possible that relaxed jeans are the ideal option for more muscular men.

A brand with an athletic fit, on the other hand, will give you a little extra room in the seat and thighs without being overly baggy at the bottom.

My main problem with relaxed-fit jeans is this. They make you look heavier and shorter and have a swampy appearance towards the bottom.