If you’ve been into boots for a while, I’m sure you’ve also started to dabble in the world of sick denim fades.
Or maybe you started with a love of raw denim and moved on to boots?
In either case, once you start down the rabbit-hole, pairing the best boots with the best denim is inevitable.
I started with boots. And after trying several fantastic denim brands, I think I’m a denim guy now, too.
These are my favorite jeans to pair with high quality Goodyear welted boots.
6 Most Important Types of Denim “Cuts” to Know When Pairing with Your Boots
It took me a long time to figure out what type of denim cut works best with my body. So I’m going to explain the different cuts of jeans and the type of boots they work best with. Plus, I’ll give my recommendation on which cuts to avoid.
Skinny
Skinny jeans are narrow through the thigh and taper strong below the knee.
This is definitely a younger style and I never recommend it to guys over 30 years old, unless you’re super skinny and are one of those guys who looks cool all the time. But there are only 12 of those guys out there, so you’re probably not it (sorry, but I’m not either).
Skinny jeans look the best when paired with “sock-like” Chelsea boots that are really low profile—the style is more of that rock-and-roll vibe. Again, dudes in their early 20s can pull that off pretty easily, but it’s a fine line if you’re pushing 30 or above. I’d just stay away.
Slim-Tapered
Slim-tapered jeans are the refined gentleman’s alternative to skinny jeans. I’m a pretty big dude at 6’1” 200 lbs, and I have one pair of slim-tapered jeans that I really like (the Kato jeans I recommend a little later).
Slim jeans have more room in the seat and thigh compared to skinny jeans, but they’re still very crisp and narrow. They have a decent amount of taper below the knee, too.
This style of jean looks great with slimmer, more narrow boots. A great example is pretty much the entire Thursday Boot Company collection.
I find that Thursday Boots have the streamlined style that pairs really well with a tapered jean. Other more bulky boots like the Red Wing Iron Ranger look too big when paired with a jean that’s tapered below the knee.
Slim-Straight
Slim-straight is just as narrow a slim through the thigh, but there’s no taper below the knee.
A slim-straight jean is a great choice if you don’t have very large thighs, but you still like to wear more bulky boots like Red Wings or Wolverines.
I personally don’t like how slim-straight jeans look on me. I have large thighs (my PR is a 365lb squat, baby), so I find that slim-straight jeans hug my thighs tightly, but the lack of taper makes it look like I’m wearing bell-bottoms. For that reason, I just bump up to straight cut jeans for the added room in the seat and thigh.
But that’s just my body type—guys with more rational-sized thighs might feel like they’re swimming in straight cut jeans, so a slim-straight would make more sense for them.
Straight
Straight cut jeans are my personal favorite. They have plenty of room in the seat and thigh and they’re straight all the way down to the leg opening.
I’ve started wearing a lot of boots from Red Wing, Nicks, Whites, Wesco, Truman, and Grant Stone, and these boots are all a little more on the bulky side, at least when you compare them to a brand like Thursday.
Pairing a bulkier, high quality boot with a straight cut pair of jeans is a more mature look that I think is more fitting for guys at 30 and beyond. Plus, usually 20 year olds don’t have enough money to justify buying a $300 or $400 boot, so the slimmer, more dressy and fashion-forward boots are a better choice financially.
For me, straight cut jeans still fit pretty snug at the seat and thigh (did I mention that I squat 365 yet? Yeah, I lift bro), but they don’t look tight like a slim fit would.
There’s no taper below the knee, so they land on your boots the same way a slim-straight jean would.
Boot Cut
Boot cut jeans flare out a bit below the knee. I don’t personally wear any boot cut jeans, but they’re the go-to choice for cowboy boots.
However, I actually like wearing my straight cut jeans with cowboy boots. That’s in part because of my personal style. I’m more into the heritage fashion style rather than western style with the big belt buckle and can of chew in the back pocket.
Relaxed
Relaxed jeans are another fit that I avoid. For huskier gents, relaxed jeans may be your best bet, but I would suggest at least going and trying on a pair of straight cut jeans. Or if you can find a brand with an “athletic” fit, that’ll give more room in the seat and thighs without too much bagginess at the bottom.
That’s my big issue with relaxed fit jeans—they seem “swampy” at the bottom and they make you look heavier and shorter.
How Did I Come Up With My List?
I tried 10 of the most popular brands, read through dozens of reviews to land on those 10, and scoured forums filled with denim-heads and fashion enthusiasts to get these recommendations.
I’ll be showing you what these jeans look like, and which type of boots I like to pair with them so you can get a better idea of what I’m talking about.
My Recommendations
Best Overall: Raleigh Denim Workshop Graham
When the legendary White Oak Mills closed down their denim mill, Raleigh Denim Workshop went searching for the best alternative. They found something strikingly similar---now their raw selvedge jeans from the Nihon Menpu mill in Japan are my favorite jeans to pair with boots.
They age beautifully and the break in is surprisingly easy for raw denim.
The Raleigh Denim Workshop Graham jean is made with Nihon Menpu denim from Ibara, Japan.
Apparently the founder of Raleigh Denim chose this specific fabric because it was the closest he could find to the legendary original Cone White Oak denim out of Greensboro, North Carolina.
Now, I don’t know much about Cone White Oak denim, but I can say that this particular fabric is outstanding. It feels lightweight but sturdy at 13 oz, with a nice looking red chain stitch hem and a red stitch on the selvedge detail.
It’s made with natural indigo, which definitely makes these jeans more on the pricey side of things, but the way it fades and ages is beautiful.
I like the Graham cut because it’s most similar to a straight cut jean, but with a little bit of taper through the leg. These look fantastic when paired with my Wesco Mr. Lou boots, and they go really well with Nicks and Red Wings.
What I Like
The natural indigo dye looks beautiful new and ages with a very distinct style.
Details like the red chain stitch along the hem and selvedge stripe make these jeans look rich.
The cut is roomy enough for comfort but still trim and neat looking.
What I Don’t Like
Limited fabric options when shopping the Graham.
What Other Reviewers Say
Raleigh Denim Workshop has a reputation for being immediately comfortable, which isn’t always true with other raw denim.
Reviewers seem to like that Raleigh Denim is more focused on the overall fit and feel of their jeans, rather than making the stiffest, most badass jeans possible (which some denim brands do).
The Verdict
For a high-end jean that looks fantastic with high-end boots, I like the Raleigh Denim Workshop Graham.
These are the kind of jeans that’ll complement Wesco, Nicks, Whites, Vibergs—the good stuff.
I like the Graham fit because it has plenty of room in the seat and thighs, and the opening is slightly tapered, so you have some room to show off the leather of your boot, but the boot doesn’t get swallowed up.
I have the Nihon Menpu fabric version, and it’s definitely the highest quality fabric I’ve ever experienced with jeans.
When the legendary White Oak Mills closed down their denim mill, Raleigh Denim Workshop went searching for the best alternative. They found something strikingly similar---now their raw selvedge jeans from the Nihon Menpu mill in Japan are my favorite jeans to pair with boots.
They age beautifully and the break in is surprisingly easy for raw denim.
Best Slim-Tapered: Hiroshi-Kato Scissors
The Kato brand Scissors jeans are made with the brands own 10.5oz Air Raw selvedge denim, which is a really unique fabric. Plus, because it’s not just 100% cotton, it has some 4-way stretch to it, which makes it really comfortable.
The Hiroshi-Kato Scissors is the exact pair of jeans I’ve been looking for my whole life. And when I finally found them, my legs got too big.
Yes, I’ve been hitting the weights, so I’ve outgrown all of my slim-tapered jeans. But right before I did, I found what I consider to be the best fit and the best overall look for a slim-tapered jean.
The Kato brand Scissors jeans are made with the brands own 10.5oz Air Raw selvedge denim, which is a really unique fabric.
It looks and feels way heavier—much more like a 16 or 18oz denim, but it’s comfortable and light like a 10oz denim. Plus, because it’s not just 100% cotton, it has some 4-way stretch to it, which makes it really comfortable.
Even though it has stretch, they still fade nicely and break in to get you that DIY patina that denim enthusiasts love.
Kato jeans are my go-to pairing with Thursday boots. Because Thursdays are slimmer and more sleek, you want that significant taper below the knee to match the boot.
What I Like
The fabric has 4-way stretch, so it’s a lot more comfortable than most raw denim.
The fabric looks much heavier than it is, and that’s because of a unique weaving pattern.
The price is very reasonable considering the quality.
What I Don’t Like
Hiroshi Kato doesn’t offer many pure raw selvedge options—they have a lot of washes and fades, but only a few choices for the purists.
What Other Reviewers Say
Reviewers who’ve tried several raw selvedge denim brands enjoy how comfortable Kato brand jeans are. That’s one thing that comes up time and time again for their Air Selvedge denim—many say they’re the most comfortable raw jeans they’ve ever worn.
The Verdict
If you’re looking for the best slim-taper jean to complement your dressier boots, take a look at the Kato Scissors.
After trying dozens of brands, this is the exact fit I’d been looking for. They match the slim, sleek profile that boots brands like Thursday offer. So if you have a casual style that matches that type of boot, these are the jeans for you.
The Kato brand Scissors jeans are made with the brands own 10.5oz Air Raw selvedge denim, which is a really unique fabric. Plus, because it’s not just 100% cotton, it has some 4-way stretch to it, which makes it really comfortable.
Best Stretch: Flint and Tinder All-American Stretch Denim
Flint and Tinder’s signature All-American Jeans are cut, sewn and finished in Los Angeles, California. The result: American-made denim that's extremely comfortable.
My first pair of raw denim jeans were hilarious—they were so uncomfortable, I don’t think I ever broke them in. I just ended up giving them away.
Sometimes it makes you wonder if denim-heads secretly wear stretchy pants when no one’s looking.
If you want a jean that has that deep indigo dye but has some Spandex loaded in the fabric for comfort and stretch, then definitely check out the Flint and Tinder All-American Stretch Denim.
I picked mine up in a straight cut and the fit is fantastic. Plus, they’re maybe the most comfortable jeans I own.
These jeans are built in Los Angeles, so you’re getting a 100% USA-made jean. The back pocket detail is nice and simple, and these jeans have a classic smooth texture that looks great both casually and if you want to dress them up a bit.
What I Like
The added 1% Spandex gives these a lot of stretch and makes them super comfortable.
The back pockets are plain, with a wide stitch at the sides for added durability.
They offer a variety of inseam lengths.
What I Don’t Like
Not a lot of color and size options.
What Other Reviewers Say
Comfort is the big buzzword in the reviews. A lot of serious denim buyers seem to like these jeans as more casual, comfortable backups to their weighty, stiff jeans. I can see where wearing still raw denim all day could break a man down.
The Verdict
Purists might only want 100% cotton, but there’s something to be said for all the extra comfort you get with just a bit of Spandex added in.
If you like a stretch jean, my favorite is Flint and Tinder. They’re USA-made, and the deep indigo color and simple design makes their jeans a versatile choice for all levels of casual wear.
Flint and Tinder’s signature All-American Jeans are cut, sewn and finished in Los Angeles, California. The result: American-made denim that's extremely comfortable.
Most Iconic: Levi’s 501
Possibly the most well-known jeans around, the 501s are the quintessential 'original' Levi's. It's a style that's endured since known since 1873, featuring the original straight fit for an All-American look with a button fly and 5 Pocket Styling.
The Levi’s 501 is legendary. It’s the jean that started it all.
And I have to say, they’re pretty cool.
After not wearing Levi 501’s for maybe the past 20 years, I recently picked up a pair and I’ve been wearing them non-stop.
Now, I picked up a super light wash because I already have plenty of deep raw indigo pairs. But the fit is so comfortable and the straight cut looks fantastic with my favorite boots like these Red Wing Iron Rangers.
I don’t necessarily think the colors you’re seeing in the picture go well together, but I want to give you an idea of how these jeans rest on the boot and what the overall profile looks like.
You can get a black pair of 501’s to match black boots, or a darker indigo to complement your brown boots.
What I Like
I love the button fly.
The fabric is soft and comfortable and comes broken in.
There are tons of washes and size options.
What I Don’t Like
I wish Levi’s would regularly make raw selvedge versions of their 501.
What Other Reviewers Say
Folks in the USSR would smuggle these jeans across borders to sell them for multiples of what they originally cost. If that doesn’t tell you something, then I don’t know what will. No other jeans on this list have ever had a history of being smuggled and sold on black markets.
The Verdict
The Levi’s 501 is an oldie, but a goodie. I wish Levi’s would make a raw selvedge version, but what they do make is still that same great All-American look that was around in the 50s and 60s.
I have a light wash pair of 501’s, but I’m already looking at the darker washes and planning on getting another pair.
The price is fantastic—much lower than $100, so these are definitely the most budget-friendly jeans on my list.
Possibly the most well-known jeans around, the 501s are the quintessential 'original' Levi's. It's a style that's endured since known since 1873, featuring the original straight fit for an All-American look with a button fly and 5 Pocket Styling.
Best Heavyweight: Ironheart 634
The 634 is made with several types of fabric, but the most popular version is made with a 21oz real indigo dyed raw Japanese selvedge fabric. There is no other jean/denim combination that is so quintessentially Ironheart.
The Ironheart 634 is one tough jean. There’s a reason the brand is called Ironheart—they’re not for the faint of heart.
The 634 is made with several types of fabric, but the most popular version is made with a 21oz real indigo dyed raw Japanese selvedge fabric.
Ironheart is to jeans what Grant Stone and Truman Boot Company is to boots: they make denim for denim-lovers and the prices are extremely fair for the quality you’re getting.
That doesn’t mean they’re cheap. But the value-for-money is exceptional.
Note that Ironheart doesn’t use vanity sizing, which all the other brands on this list do. That means you’ll actually want to measure your waist size and get that measurement, rather than go off of what your usual jean size is.
For example, my usual jean size is a 34. That’s what I get with Levi’s, Raleigh Denim, Kato, etc. But my waist is actually 35-36 inches around. So my best fit for Ironheart is probably a 36. The Ironheart 36 is going to fit more closely to the size 34 in other brands.
That difference in sizing standards can be one of the difficult things about switching from standard jeans over to the real-deal denim-enthusiast brands. And beyond sizing, these just aren’t that comfortable.
If you love boots, you’re no stranger to a break in period. And the 21oz Ironheart 634 needs several weeks (some say months) to full break in to the point where they’re comfortable.
Whatever you do, don’t break in your boots and a new pair of jeans like this at the same time unless you’re specifically repenting for a whole laundry list of sins. In that case, throw on a burlap shirt and bring a self-flagellation whip.
What I Like
21 oz fabric is so tough and looks unique.
There’s a community around these jeans and among those who’ve taken the time to break them in.
They offer a large selection of waist sizes.
What I Don’t Like
The break in period is lengthy and can be difficult.
What Other Reviewers Say
Ironheart is a denim-lovers brand. As such, they have a loyal following of reviewers who load forums with tons of images of what these jeans look like after months of wearing and fading.
Reviewers love the number of choices they have for heavyweight denim in the Ironheart 634 style.
The Verdict
If you want to dive into the denim deep-end, the Ironheart 634 is a fantastic place to start. Their 21 oz denim is heavy, but believe it or not, you can go even heavier with their 25 oz fabric.
21 oz is tough. 25 oz is just ridiculous.
I’d personally stick to 21 oz if you’re looking for a good heavyweight denim that’ll age, fade, and break in and look right at home with your favorite boots.
The 634 is made with several types of fabric, but the most popular version is made with a 21oz real indigo dyed raw Japanese selvedge fabric. There is no other jean/denim combination that is so quintessentially Ironheart.
Which Is Best for You?
The dream is when you have a closet full of faded jeans and well-worn boots.
I pick out my jeans for different purposes. Mostly, I wear straight cut jeans with more casual boots like my Red Wings, Wesco, and Nicks.
For that style, I love my Raleigh Denim Workshop jeans.
When the legendary White Oak Mills closed down their denim mill, Raleigh Denim Workshop went searching for the best alternative. They found something strikingly similar---now their raw selvedge jeans from the Nihon Menpu mill in Japan are my favorite jeans to pair with boots.
They age beautifully and the break in is surprisingly easy for raw denim.
When I’m taking my wife out for a date and want to look more trim and sleek, I throw on the Kato brand Scissor slim tapered cut jeans. And I don’t wear those too often so they don’t have much fade, which looks better in more upscale casual scenarios. For my boots, I’ll put on one of Thursday’s more dressy options, like the Rogue jodhpur.
The Kato brand Scissors jeans are made with the brands own 10.5oz Air Raw selvedge denim, which is a really unique fabric. Plus, because it’s not just 100% cotton, it has some 4-way stretch to it, which makes it really comfortable.
But there are plenty of other amazing jeans out there, too. The Levi’s 501 is an icon for a reason, and Flint and Tinder makes an outstanding stretch fabric jean.
Possibly the most well-known jeans around, the 501s are the quintessential 'original' Levi's. It's a style that's endured since known since 1873, featuring the original straight fit for an All-American look with a button fly and 5 Pocket Styling.
And for those who want a heavyweight jean they can tell war stories about, the Ironheart 634 is the ticket with its beefy 21 oz cotton fabric.
So what will it be for you?
FAQs
Do slim fit jeans work for boots?
Yes, slim fit jeans work really well with boots. If you wear more narrow boots, you can even get a slim-tapered jean. If you wear bulkier boots like Red Wing, you may want a slim-straight cut jean.
What jeans look best with boots?
The best looking cut of jean to pair with boots in my opinion is a straight cut jean. The leg opening is wide enough to show off some leather and leave you plenty of room to move around, but it’s not so wide that the fabric overwhelms the boot.
Are skinny jeans still in style?
Skinny jeans aren’t really in style any more. Slim guys in their 20s still look great with skinny jeans, but anyone with some meat on their bones or over 30 should stick to slim and straight jeans.
