The Best Shoes to Wear with Chinos

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There are few pieces in a man’s wardrobe more essential than a good pair of chino pants.

Arguably the most versatile pants you can own, the beauty of chinos is that they can work in a wide range of situations:

They can stylishly satisfy the dress code in formal settings like business-casual offices and semi-formal events, and work just as well on more casual occasions like house parties or warm weather barbecues.

But the key to maximizing chinos’ versatility without sacrificing style is knowing how to select the right type of shoes to pair with them.

To help ensure your smart-casual look is as optimized and attractive as possible, in this post we’ll break down more than a dozen of the best shoes to wear with chinos, and explain how, and when and where to wear them for maximum effect.

What Shoes to Wear with Chinos

Breaking Down the Best Shoes to Wear with Chinos

Best Casual Shoes for Men with Chinos ↓

A good pair of chinos can certainly be dressed up in a way that satisfies the dress code of most semi-formal occasions.

But fundamentally, they’re still considered pretty casual pants.

With that said, even the most casual chinos can still look sharp when you wear them with a stylish pair of shoes that complements – and even elevates – the rest of your outfit.

Each of the shoes below will help you do just that.

Plus, they have the added benefit of working well with various different styles of pants, so you don’t have to spend your shoe budget on kicks that only work with pants made from chino cloth.

White Sneakers

Man wearing white sneakers
[Image: cottonbro / Pexels]
How to Wear Chinos with Sneakers: 

The same thing that makes a white pair of sneakers perfect for the summer months also makes them a great option to wear with chinos:

They’re comfortable, stylish, and versatile as hell.

Nowadays a crisp, minimalist pair of white leather sneakers can be worn just about anywhere, including most smart casual events and business casual offices.

Plus, white shoes can be paired with just about any type of chinos, from fancier dress trousers and navy chinos to casual khaki pants in laid back, lighter shades.

Sharp Selections: 

Boat Shoes

Man wearing chinos and boat shoes
[Image: Sperry / Instagram]
How to Wear Boat Shoes with Chinos:

Boat shoes’s nautical origins make them inherently more laid back than other types of leather loafers. 

They work great with casual khaki chinos in light, summery colors – think white chinos or a really pale shade of beige chinos – and tend to pair well with polo shirts or another style of casual shirt. 

Pro Tip:

While boat shoes are a great casual option, it’s important to keep in mind that they’re not a great match for formal wear. 

If you’re going anywhere that requires wearing a jacket, it’s probably a good idea to skip the chinos-and-boat-shoes look in favor of dress pants and some slightly more formal shoes, like any of the dress shoe options listed below.

Sharp Selections: 

Driving Shoes 

Man wearing chinos and drivers
[Image: Wolf & Shepherd]
How to Wear Driving Shoes with Chinos:

Driving shoes are essentially a casual pair of loafers. 

They usually have a slightly squared-off toe box and a rubber sole, both of which make them more comfortable and effective to wear while you’re putting the pedal to the metal

I like to think of driving shoes as basically a land-locked version of boat shoes. 

They have a lot of the same style and can be worn in a lot of the same situations, but because they’re not so closely associated with the sea, they’re actually more versatile, and can be worn in a wider array of casual settings.

Since I live in the city and rarely find myself near water, I invested in a great pair of suede loafers / driving shoes a few years back, and they’ve basically become my go-to shoe for summer.

Sharp Selections: 

Black Sneakers

Man wearing chinos and black sneakers
[Image: Maksym Tymchyk / Unsplash]
How to Wear Black Sneakers with Chinos:

Black shoes tend to be considered more formal and sophisticated than other shoe colors, even when we’re talking about sneakers. 

While nothing can quite live up to the sophistication of black dress shoes, a sleek and minimalist pair of black leather sneakers can be a slightly more casual alternative that still looks great with formal chinos and a crisp white dress shirt, but provides a lot more comfort. 

(In fact, black sneakers are a favorite of waiters and retail workers, who often need shoes that are sleek enough to pair with black chinos, but comfortable enough to stand in all day.)

Sharp Selections: 

Crossovers / Hybrids 

Man wearing chinos and hybrids
[Image: Cole Haan]
How to Wear Crossovers with Chinos:

A relatively new look that a lot of guys still don’t necessarily think of when coming up with outfit ideas, crossovers combine the refined toe shape of dress shoes with the comfort and support of athletic shoes. 

The result is a sporty, crisp look that can work with a lot of different types of chinos or khaki. 

(Not to mention a good choice for other casual pants like jeans, joggers and those stretchy kind of jogger-chino hybrids you see from a lot of athleisure brands these days.)  

Sharp Selections: 
Deep Dive:  

Check out our in-depth Wolf & Shepherd review to find out how their Swiftknit crossovers hold up under scrutiny.

Best Boots to Wear with Chinos ↓

Chelsea Boots

Man wearing chinos and chelsea boots
[Image: Amberjack]
How to Wear Chelsea Boots with Chinos:

Chelseas are to the boot world what chinos are to the world of pants:

Halfway between casual comfort and dressed up formality.

On the comfort front, they have elastic vents at the side that offer easier access than laces.

But today the best brands make them with a sharp toe shape that’s just as sophisticated as traditional dress shoes, and helps them elevate your overall look.

Sharp Selections: 

Work Boots or Combat Boots

Man wearing chinos and work boots
[Image: Annie Spratt / Unsplash]
How to Wear Work Boots with Chinos:

Pairing chinos with a chunky pair of work boots lends them a bit of blue collar ruggedness that makes them (and you) look hard-working and resilient. 

Similarly, pairing them with a good pair of Red Wings or other combat boots evokes the (dapper) uniforms of WWII era soldiers, lending your look a classic bit of military grit.

Sharp Selections: 

Chukka Boots / Desert Boots

Man wearing chinos and chukka boots
[Image: Thursday Boot Co.]
How to Wear Chukka Boots with Chinos:

And speaking of WWII era military grit, desert boots are styled after (and named for) the boots worn by British soldiers during desert campaigns. 

Off the battlefield, they’ve long been known as the preferred boot of style icons ranging from Steve McQueen to James Bond, and are arguably the most versatile boot style guys can own. 

They’re perfect for chinos because, much like the pants themselves, they can be dressed up or down while providing plenty of comfort, support and protection from the elements.

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.

A (Quick) Note on Colors: 

Choosing the Best Color Boots with Chinos 

Brown boots tend to pair best with masculine, earth-tone chinos like the colors pictured here

While boots are available in a wide variety of different colours nowadays, the most versatile options to pair with chinos are the two most classic looks:

Brown boots are the best choice if you wear a lot of blues, greens or earth tones like khaki and beige. 

But as mentioned above, black boots can be a little more sophisticated, and work well if your personal style leans toward darker shades.

Best Dress Shoes to Wear with Chinos ↓

One thing that sets chinos apart from jeans – and makes them so damn popular – is that they can be dressed up or down. 

And with due apologies to blazers and formal shirts, the truth is that there’s no better way to make chinos look more sophisticated – and elevate your entire look – than by pairing them with the right shoes.

So let’s break down the best types of dress shoes to wear with chinos, and go over some top tips for making each type look as sharp as possible. 

Cap Toe Shoes

cap toe shoes
[Image: Beckett Simonon]
How to Wear Cap Toe Dress Shoes with Chinos:

Cap toe is more of a shoe style than a shoe type, since a lot of the different types of shoes below are available in cap toe models. 

But cap toes just happen to be my personal preference because, in the opinion of this humble style blogger, a good cap toe can make shoes look more sophisticated and stylish. 

And since the handsome devil is in the details, any little bit of sophistication can help you stand out from the crowd.

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 chinos and monk strap shoes
[Image: Allen Edmonds / Instagram]
How to Wear Monk Straps with Chinos:

Speaking of sophisticated looking shoes, a good pair of monk straps is a great way to elevate your chinos or casual pants. 

Monks can be worn with everything from formal suits to a pair of dark wash jeans (or better yet, dark blue chinos), so they’re a versatile shoe to have in your arsenal. 

As their name implies, monk straps use leather straps and metallic buckles to seal the shoe up, instead of traditional laces. 

The result is a leather-heavy look that nicely straddles the line between rugged and refined — and helps your chinos do the same.

Sharp Selections: 

Oxford Shoes 

Oxford shoes
[Image: Beckett Simonon]
How to Wear Oxfords with Chinos:

A classic dress shoe style, Oxfords are characterized by their closed lacing, which means that the laces are sewn underneath what’s called the vamp (aka the front part of the shoe). 

This gives Oxfords a cleaner look, which makes them a popular choice for more formal occasions.

If you’re looking for a timeless shoe that you can wear with your best chinos and a crisp white shirt (or formal shirts of various colors), Oxfords are a great option. 

Sharp Selections:

Derby Shoes

Man wearing chinos and derby shoes
[Image: StepPro / Shutterstock]
How to Wear Derby Shoes with Chinos:

Unlike Oxfords, Derby shoes have an open lacing system, which means that the laces are sewn on top of the vamp. 

This gives Derby shoes a more relaxed look, making them a great choice for everyday wear, when your whole look is a little more casual.

But with that said, a well made pair of Derbies with a sophisticated toe shape can still look plenty put together, so you’re not necessarily sacrificing any style by option for a Derby over an Oxford.

Penny Loafers

Man wearing chinos and penny loafers
[Image: Miad Vosoughi / Shutterstock]
How to Wear Penny Loafers with Chinos:

With penny loafers, the toe box plays an important role in determining whether the shoe is a dress shoe, or more casual. 

Some penny loafers have a slightly squared off toe, which gives them a more relaxed and casual vibe that almost makes them look like drivers. 

Others have a sharper, more sophisticated shape that more closely resembles Oxfords and other traditional dress shoes, making them look more formal. 

Both styles can work great with chinos, depending on whether you want a dressier shoe, or something you can wear every day.

Sharp Selections:

Wingtips / Brogues 

Man wearing chinos and wingtips
[Image: Benjamin Rascoe / Unsplash]
How to Wear Brogues with Chinos:

The perfect way to add a little ruggedness to your look without going all the way to a full boot, wingtip shoes owe their origins to English hunting parties: 

The small holes in the shoe, called broguing, were immediately meant to allow water to release from the shoe, helping keep the hunters’ feet dry. 

(Although today it’s worth noting that the broguing is just decorative. Turns out shoes full of small holes aren’t actually all that practical…) 

The perfect way to wear wingtips with chinos is to work both into your fall wardrobe, when the rugged, outdoorsy origin of the shoe will nicely complement the natural cotton twill of chinos. 

Plus, the various different colors of fall chinos – think browns, oranges and dark greens – tend to work great with a handsome pair of dark brown brogues, making autumn the perfect time to pair them up.

Sharp Selections: 

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

Banner Image: Benjamin Rascoe / Unsplash | Illustration: Irreverent Gent

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.