The Most Stylish Shoes for Men to Wear with Jeans

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Around here we like to say that shoes are the secret weapon of style. 

But, as hard as we try to get the word out, it seems like a lot of guys still haven’t gotten the message—especially when they’re wearing jeans. 

man wearing jeans and sneakers jumping on stairs
[Image: Benjamin Rascoe / Unsplash]

Pairing ​the right type of jeans with the right pair of shoes can elevate your entire appearance, and take an otherwise casual look from standard to stylish. 

But when you just slap on any old shoes with your favorite pair of jeans, you miss a golden opportunity to make yourself look sharp. 

Even worse, choosing the ​wrong kind of casual footwear isn’t just a missed opportunity—it’s a detriment that can drag down your overall attractiveness. 

As Huffpost reported in 2017, 64% of women judge a man’s fashion sense based on his shoes, and 52% go so far as to use a man’s shoes to judge his personality. 

To help you make your casual appearance as attractive as possible, in this post we’ve rounded up more than a dozen different styles of shoes to wear with jeans, each of which will help you look more dapper in denim.

The Best Men’s Shoes to Wear with Jeans

Breaking Down the Best Shoes to Wear with Jeans Men Need to Know About

Best Casual Shoes for Men with Jeans ↓

Jeans have come a long way since they were invented by Jacob W. Davis back in 1871. 

But thanks to their rugged and blue collar origins, to this day jeans are still largely considered a more casual style of pant. 

So let’s start with some of the best-looking casual shoes that will pair well with jeans in a wide variety of different occasions and casual situations.

White Sneakers

man wearing jeans and white sneakers
[Image: Benjamin Rascoe / Unsplash]

A clean pair of classic sneakers will lend your casual outfit a hip, youthful and even (vaguely) athletic vibe. 

They’re a great option for super casual occasions like running errands or meeting friends for brunch, when you want to feel comfortable while still expressing strong personal style. 

The go-to movie is to pair white sneakers with slim jeans in a dark wash. 

But they also work well with light wash blue jeans, especially during warmer months, when you can opt for lighter-weight canvas shoes, as opposed to traditional white leather sneakers. 

Sharp Selections: 

Boat Shoes

man wearing jeans and boat shoes
[Image: Sperry]

Boat shoes ranked high on my list of the best casual men’s shoes, so it’s no surprise to see them showing up here. 

With rubber soles and a more squared-off toe than most dress shoes, they’re distinctly casual, but more sophisticated and refined than sneakers. 

The quintessential pair comes in brown leather, but nowadays lots of brands are making them in cool colors and fabrics, too. 

Pro Tip: 

Because boat shoes evoke a more nautical vibe, the best way to wear them is to skip the socks, which is why they’re often considered one of the best summer shoes. 

Sharp Selections: 

Black Sneakers

man wearing black sneakers
[Image: Naufal Giffari / Unsplash]

Black shoes tend to be associated with formal wear, so rocking a black pair of sneakers with your jeans is a great way to give your casual wear a slightly dressier look. 

For instance, pairing a plain white t-shirt with dark denim and white sneakers is a classic casual look. 

But replacing the white sneakers with black ones lends the whole look both an air of sophistication and a slight edge, both of which help elevate it. 

Sharp Selections: 

Driving Shoes 

man wearing driving shoes and jeans
[Image: Wolf & Shepherd]

Driving shoes are basically a land-locked version of boat shoes. 

They’re traditionally leather shoes, but the rubber sole (which helps your foot grip the pedals while driving, hence the name) makes them more casual than a pair of dress shoes. 

As a result, they’re kind of the perfect shoe to pair with denim if you want to go for the smart casual look: 

They’re slightly dressier and more formal shoes than sneakers, but still casual enough to give you a relaxed look that’s put together without feeling too try-hard. 

Sharp Selections: 

Crossovers / Hybrids 

man wearing jeans and crossover shoes
[Image: Benjamin Rascoe / Unsplash]

Of all the different types of shoes on this list, this style is probably the newest. 

In recent years a lot of brands have started taking the traditional elements of classic shoes and combining them with other styles to create hybrids that are somewhere between both. 

You can find dress shoes that feel like sneakers, which combine quality leather and a padded sole, derby shoes made from breathable polyester, and pretty much every other combo under the sun. 

These types of hybrid models are a great choice for daily wear and perfect for pairing with slim cut or straight-leg jeans. 

They’ll help lend you a semi-formal look while providing a lot more comfort and support than most dress shoes. 

Sharp Selections: 

Hybrid Boots

Winter crossovers

OK, forget what I said above – this style is definitely the newest.

After the (fairly massive) success of hybrid/crossover shoe styles, shoe companies started applying the same treatment to boots.

As someone whose tastes tend toward the classic, I have to admit that I was pretty skeptical at first.

To me one of the big advantages of boots – and one of the reasons why they work so well with jeans – is the fact that they’re hardy and substantive, which is what makes them more masculine.

But as it turns, your footwear doesn’t need to be heavy in order to be hardy.

Hybrid boots still have a significant leather upper, just like regular ankle boots.

And that’s more than enough to give them a hardy, masculine appeal, even when they sport a sneaker-like sole that’s soft and cushioning.

The result is perfect for wearing with jeans because it’s simultaneously rugged and comfortable, just like denim.

Sharp Selections:

Work Boots

man wearing jeans and work boots
[Image: Nathan Dumlao / Unsplash]

A comfortable pair of work boots is an obvious choice on the job site, where boot cut jeans tend to be the dominant denim style. 

But rocking a chunky pair of work boots with lighter wash jeans is a classic look that works just as well on the street as it does on the job. 

There are a few simple rules to remember when wearing work boots casually: 

First, remember that big, chunky boots look best with a looser cut of jeans, so that the ankle of the pant can encompass the top of the boot. 

Second, keep in mind that a tan color work boot pair well with anything from a lighter wash to a dark blue jean. 

But if your boots are a darker color, your jeans should be too. 

Sharp Selections: 

Chelsea Boots

man wearing jeans and chelsea boots

Chelsea boots come in a wide range of different shapes, sizes and colors, but they’re defined by the fact that they don’t have laces. 

While Chelseas can certainly have a svelte toe shape that makes them look sophisticated, as a general rule pull-on boots are considered more casual, which is what makes Chelseas perfect for pairing with jeans. 

Sharp Selections: 

Chukka Boots / Desert Boots

man wearing jeans and chukka boots
[Image: Thursday Boot Co.]

 Another style that can skirt the line between casual and formal, chukkas – also known as desert boots – are always a smart look when paird with jeans. 

As with chelseas, chukkas are the kind of shoes that can be made to look as sleek as dress shoes (James Bond wore them with a suit in Skyfall) or as casual as deck shoes (007 rocked a different pair in Quantum of Solace, pairing them with white jeans to chase down bad guys in the desert). 

Both styles work well with jeans, but remember that the sleeker your shoes are, the slimmer your jeans should be. 

Sharp Selections: 
Deep Dive:  

For more stylish desert boots, check out our complete round-up of the best men’s chukka boots on the market.

Cowboy Boots

man wearing jeans and cowboy boots
[Image: Phinehas Adams / Unsplash]

 This one comes with a huge caveat: 

There’s no denying that cowboy boots can look badass with a pair of jeans, but context is everything here. 

If you live in a Western state where cowboy boots are at least somewhat common, then by all means throw on a pair when you’re out and about. 

But if you don’t live in a home where the buffaloes roam, then proceed with extreme caution. 

No matter how cool you may think cowboy boots look, if they’re not geographically or situationally appropriate, you’ll end up looking more like a cosplayer than a cowboy. 

Sharp Selections: 

Best Dress Shoes for Men with Jeans ↓

As mentioned, jeans are an inherently casual type of pants, so any of the casual shoes mentioned above will provide a good option that’s perfectly acceptable. 

But why settle for acceptable when you can look exceptional? 

Pairing a slim pair of jeans with a sharp pair of dress shoes will elevate your appearance even further, and help take your entire look to the next level. 

Here are a few of the best styles of dress shoes to wear with denim.

(But for the love of Thor, please remember: never pair your dress shoes with white socks. In fact, don’t ever wear white socks, unless you’re not going to the gym or embarking on some other athletic endeavor.) 

Cap Toe Shoes

cap toe shoes
[Image: Beckett Simonon]

Cap toes are kind of a funny category of dress shoe, since technically a number of the shoe styles below could have a capped toe. 

But in my opinion a capped toe adds a touch of class and sophistication to shoes and boots, which warrants a separate call out on the list. 

Pairing a slim pair of jeans with a cap-toed shoe in a sleek-but-not-too-pointy toe shape instantly elevates your denim, and can help turn an otherwise casual look into a semi-formal outfit. 

Sharp Selections: 
Deep Dive:  

Check out our full Beckett Simonon review to see how their cap toe shoes held up after rigorous testing.

Monk Straps 

man wearing jeans and double monkstrap shoes
[Image: Allen Edmonds]

Monk straps are a great style of dress shoe to wear with jeans because the metallic buckles on the straps evoke denim’s rugged origins, while still looking refined. 

If you’re wearing monk straps, make sure your jeans are not just slim-fitting, but relatively short:

You don’t want too much excess fabric bunching up at the ankles, which might cover the straps and risk sacrificing some of their stylish effect. 

Sharp Selections: 

Derby Shoes

derby shoes
[Image: Scarosso]

Known for their open lacing, which distinguishes them from the closed lacing of Oxfords, the Derby is a classic dress shoe style that looks just as good with jeans as it does with a suit.

If you’re looking for a classic style that’s sharp without being too fashion-forward, Derbies are probably the right shoes for you.  

Sharp Selections:

Oxford Shoes 

Oxford shoes
[Image: Beckett Simonon]

As mentioned above, Oxfords are pretty similar to Derbies, except they have a closed-style of lacing that makes them look a little more formal. 

In fact, I wore a black pair of Oxford shoes with my midnight blue wedding tux. 

But the salesman suggested that I could get more use out of both by picking up a pair of black jeans and rocking the tux jacket with a white tee, black skinny jeans and the black dress shoes. 

I’m happy to report that he was right, and I’ve rocked the get-up quite a few times since, receiving more than one compliment along the way.  

Sharp Selections:

Penny Loafers

black penny loafers
[Image: Johnston & Murphy]

Penny loafers could argubaly be included in either section of this list: 

Many consider them casual shoes that aren’t appropriate for the office or formal events. 

But those who mostly stick to sneakers and flip flops – which, sadly, is a huge percentage of men nowadays – consider just about any shoe made out of leather to be a “dress shoe.” 

Neither camp can dispute the fact that penny loafers are more laid-back than Oxfords and Derbies, which makes them great for pairing with jeans. 

Sharp Selections:

Wingtips / Brogues 

man wearing jeans and wingtip shoes
[Image: Benjamin Rascoe / Unsplash]

We’ve saved the best for last, because wingtips (also called brogues) might just be the perfect pair of shoes to wear with jeans. 

They owe their origin to English hunting parties, when men preferred to wear shoes with small holes in the leather so that the moisture would seep out instead of staying in the shoe.

As a result, they’re arguably the most casual style of dress shoe, which makes them for pairing with jeans, which are arguably the most casual style of pants.

Sharp Selections: 

More Resources ↓
More Advice on Men’s Boots and Shoes from Irreverent Gent:

Banner Image: AmbientShoot / Shutterstock

About Dave Bowden

Dave Bowden

Founder, Irreverent Gent
Author, Man in Command and Stop Doubting, Start Dating
Writer, Really Wordy Author Bios

Dave Bowden is a style blogger, menswear expert and best-selling author (in Canada—but still!) whose advice on how to look good and live well has been featured in New York Magazine, The Wall Street Journal, Men's Health and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and two amazing sons, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.

Check out Dave's Style Story to find out how a chance encounter with his friend's step-dad taught him the value of looking good and living well (don't worry—it's less creepy than it sounds!), or email him at [email protected] if you want to get in touch.

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