Boots and denim make a great combo — but you have to get a few things right.
In the world of men’s style, there are no absolutes. Anything can look good or bad depending on the execution and context, and that’s readily apparent when you think about pairing jeans with boots.
The combination of boots and jeans conjures up a few vastly different images. For example, you might picture a stereotypically outdoorsy look with a flannel button-down.
You might imagine a refined business casual outfit with Chelsea boots and a quarter-zip sweatshirt. Or you might just think of George Strait.
The point is that there’s a wide range of ways to style boots with jeans, and you can easily adapt them to suit your personal preference. (In other words, you’re not limited to the cowboy look). But in order to nail these different styles, you have to first understand a few key principles.
How to Style Boots With Jeans
Styling boots with jeans is pretty simple, but there are a few guidelines to keep in mind when pairing these classics.
Watch Your Proportions
A good rule of thumb is to make sure your jeans and boots are proportional to one another. This means that the slimmer your jeans are, the sleeker your boots should be. Consequently, the more relaxed your jeans are, the thicker your boots should be.
If you match, say, skinny jeans with huge combat boots, you’ll get the undesirable clown shoes effect. And if you pair billowy straight-cut jeans with slim boots, you’ll look like your feet are a few sizes too small for your body.
That being said, breaking this rule isn’t always a bad thing, but you have to do it very tastefully.
For example, you can usually pair slim (not skinny) jeans with heftier boots. But if your boots and jeans are noticeably out of proportion with each other, your outfit is probably going to look not all that great.
Analyze Your Denim
You probably associate the boots and jeans pairing with two particular types of denim: slim dark wash jeans with ultra-tidy cuffs or lighter boot-cut jeans that completely hide the top part of the boot. And while these are still two popular types of jeans to wear with boots, they’re not your only options.
You can wear pretty much any style of jeans and still find a good pair of boots to go with them. The trick is to consider how the jeans are cut, what type of hems they have, and how dark or light the wash is. This will help you make sure that your boots and jeans have complementary styles.
For example, if you have dark jeans with a noticeable taper, you’ll probably want to go with a thinner boot. Similarly, if you’re going for a more laid-back vibe with medium-wash jeans that have frayed hems and wider leg openings, you’ll likely want somewhat chunkier boots (but ones that aren’t too large).
Match Your Formality Levels
For the most part, you don’t want to mix formality levels unless you’re going for an incredibly casual statement outfit — and even then, you have to do it the right way.
In general, darker-wash jeans and dress boots are considered more formal, while lighter-wash jeans and more rugged boots are more casual.
Keep in mind that most boots are more casual than formal. A few noticeable examples of dressier boots are Chelsea boots, Balmoral boots, Jodhpur boots, and some service boots and chukka boots.
Consider Cuffing
Most of the time, it’s a good idea to cuff your jeans when wearing boots. There are all kinds of ways to cuff denim, but for boots specifically, the double and pinroll cuffs are best.
If you opt not to cuff, then make sure your jeans don’t pile too much around the ankles. There should be a break at the bottom of your jeans so that the fabric doesn’t sag or cover up too much of the boot for a sloppy look.
And if you’re wearing boot-cut jeans or jeans with frayed hems, you’re better off embracing the character of your denim and not cuffing.
How To Wear Boots With Jeans for Men (10 Ways)
Now that you know the fundamental style principles behind styling jeans and boots together, get inspired by checking out these 10 outfit ideas.
The Classic Outdoorsy Look
While no style is truly timeless, this outdoorsy look comes pretty close.
It’s hard to go wrong when pairing slim jeans with work boots — as long as you avoid boots that are too chunky, you’re good to go. (If you need a starting point, try combining black or dark blue jeans with medium brown boots).
The Rugged Downtown Look
The boots with jeans look is perfect for hitting the town. This works especially well with neatly cuffed dark wash jeans and deep brown (or even burgundy) work boots.
To replicate this exact vibe, aim for structured garments with clean lines and avoid anything too relaxed or oversized.
The Smart Casual Look
Wearing boots and jeans together can look tough and rugged, but it can also look sleek and polished. Wearing slim jeans with dressier boots is an easy way to build a great smart casual outfit.
Top it off with a button-down (or, for something a bit different, a long-sleeve polo), and you’re ready for that holiday work party.
The Refined Hipster Look
Let’s set the record straight: Hipster fashion isn’t all bad. If you need proof, consider this nautically inspired outfit with its minimal yet dapper pairing of crisply cuffed jeans and two-toned boots from Taft.
This is also a good lesson in contrast — if you want to wear boots with more noticeable details or colors, go with a simpler outfit so you don’t clash.
The Elevated Gorpcore Look
Another great way to style boots with jeans is to blend elements of outdoor clothing and business casual wear. Pop on a pair of slim-straight jeans and lace up your favorite pair of work boots, and you’ve got yourself a fantastic outfit.
Alternatively, you could opt for a slim or straight cut instead of splitting the difference with a slim-straight fit.
The Seafaring Look
This outfit takes inspiration from the manual laborers and fishermen of decades past.
The single-cuffed jeans and vintage-style boots are nicely complemented by an overshirt that resembles a chore jacket and a classic striped Breton shirt. (And, of course, don’t forget the watch cap)!
The Stylish Everyday Look
Who said you can’t be extremely comfortable and stylish at the same time? Mixing formal and casual pieces is a nice way to look relaxed yet put together.
In this case, that means pairing Chelsea boots with vintage-inspired light-wash jeans. The structured jacket over the hoodie provides even more stylistic contrast to round out the outfit.
The New Heritage Look
New heritage might sound like a contradiction, but seeing it in action makes perfect sense. This outfit pairs straight fit jeans with bold boots for an undeniably cool look.
Add a couple of big cuffs and throw on some easy layers (in this case, a chambray shirt and a hickory stripe jacket) to complete the fit.
The Ready for Winter Look
Although Chelsea boots are on the dressier side, they’re still boots, so they have an inherent ruggedness to them that you can bring out with the right garments.
This outfit uses relaxed jeans, a hoodie, and a vintage jacket liner to dress down the Chelsea. For best results, go with textured Chelsea instead of smooth leather ones.
The Super Casual Look
Maybe the easiest way to wear boots with jeans is just to swap out your everyday
This simple approach works surprisingly well with most outfits, and the boots add a bit of edge that you just can’t get with shoes.
The Best Boots To Wear With Jeans
In need of a few recommendations? I’ve got you covered — here are a few excellent boots that pair excellently with all types of jeans.
Thursday Boot Company Captain
If you’re looking for a versatile boot, consider picking up the Captain from Thursday Boot Company.
This handsome ankle boot can be dressed up or down and will look fantastic with your favorite pair of jeans. Plus, it’s Goodyear welted, so you can trust it’ll last.
Oliver Cabell Chelsea Boot
The simply named Chelsea Boot from
Made from soft split Italian suede and finished with a crepe sole, this Chelsea just might be your go-to boot for dressier occasions.
Grant Stone Chukka
Grant Stone’s Chukka is a refined take on a classic. This boot is elevated enough to wear in smart casual settings but relaxed enough for more laid-back situations.
The earth colorway shown here looks particularly nice with slim, dark-wash jeans.
Dr. Martens Vegan 1460 Lace Up Boots
For a true punk-inspired look, there’s really just one option: the Vegan 1460 Lace Up Boots from Dr. Martens.
These legendary boots go perfectly with all sorts of jeans, and even better, they’re completely animal-free.
Boots With Jeans FAQ
Here are a couple of quick answers about wearing jeans with boots:
Can I Wear Black Boots With Blue Jeans?
Absolutely!
What’s the Best Boot To Wear With Jeans?
That depends entirely on the type of jeans. (See my recommendations above!)
Can Guys Wear Boots Over Jeans?
For most guys, tucking jeans into boots isn’t a good look. If it serves a functional purpose, then go ahead, but I recommend abstaining otherwise.
Boots and Jeans: A Classic Combo
Jeans and boots have gone together for a long time, and this pairing isn’t going away anytime soon. Once you’ve gotten these basic style guidelines down, experiment and put your own twist on this iconic pairing.
Questions? Comments? Leave them below!
Ask Me Anything