There’s arguably no type of pants as versatile – and essential – as a good pair of khakis.
Khaki is a neutral color that works just as well with casual wear as it does with more dressed up clothes:
Pair your khakis with a well-fitted sweater and you’ve got a smart casual look that can go almost anywhere.
Or, pair them with a navy blazer and a crisp white dress shirt, and you’ve got a more formal look that works great for everything from a business casual office to a fancy first date.
But regardless of whether you dress your khakis up or down, the key to looking sharp is to make sure your shoe choice is consistent with the overall vibe of the rest of your outfit.
To help you choose the right shoes for you, in this post we’ll break down the most stylish, essential and all around best shoes to wear with a pair of khaki pants, and show you exactly which shoe color tends to work best.
The Best Men’s Shoes to Wear with Khaki Pants
Breaking Down the Best Shoes for Khaki Pants
First Up:
What Color Shoes to Wear With Khaki Pants ↓
While choosing the right kind of shoes to wear with khaki chinos, jeans or dress pants is important, getting the right color combination is almost as essential.
So before we get into which type of shoe you should wear with khakis, let’s briefly go over the different colors that go best with khaki.
Brown Shoes
Why Wear Brown Shoes with Khaki Pants ↓
Brown is an earth tone that has a lot of the same hues as khaki, which is why any shoes with even a vaguely brown color will usually pair well with khaki pants.
What’s nice about brown is that it’s also a varied color, so you can mix and match a lot of different looks while staying in the same color family.
For instance, you could pair light khaki pants with light brown shoes for a relaxed look that’s more casual and care-free.
But wearing the exact same pair of pants with a dark brown color of shoes results in a more sophisticated look that works well for formal events.
Black Shoes
Why Wear Black Shoes with Khaki Pants ↓
(They work well with white trousers for the same reason.)
Black shoes work well with khakis because they create a nice contrast:
The starkness of the black shoes really pops against the soft, neutral khaki trousers, especially when you’re wearing a lighter shade of pants.
Black is usually thought of as a more sophisticated color, which is what makes it work so well for formal shoes.
But you can also get many of the casual shoes listed below in black, and pair them with khakis to create a more sophisticated but still casual outfit.
White Shoes
Why Wear White Shoes with Khaki Pants ↓
White shoes are, of course, basically the opposite of black, and they work well with khaki for the opposite reason.
Whereas black shoes are all about the contrast between starkness and softness, white shoes lean into the softness, helping you create a vibe that’s fresh and approachable.
During warmer months, one of my favorite looks is to pair a white top like a tee or polo shirt with a pair of khakis and white sneakers, resulting in a great combination you can wear damn near anywhere.
Grey Shoes
Why Wear Grey Shoes with Khaki Pants ↓
Gray shoes are slightly less traditional than brown, black and white, but arguably more versatile than all three of them.
Like khaki, gray is a neutral color that can be paired with pretty much any other color.
When you keep the colors on your lower body more subdued and neutral, it lets you go for a more adventurous look up top, and get away with shirts in bold, bright colors.
For instance, in the summer months my personal preference is to wear t-shirts in bright pastel shades, and pair them with a light pair of khaki cargo pants and dark grey crossover shoes.
Navy Blue Shoes
Why Wear Navy Shoes with Khaki Pants
Navy shoes are a great option if you’re looking for a less conventional color to pair with your khakis.
As mentioned above, khaki has many of the same hues as brown, and blue and brown are one of the most classically handsome color pairings in all of menswear.
Plus, navy shoes are more widely available than other non-traditional colors, like dark green or burgundy shoes, so they’re a little easier to find.
The Best Casual Shoes to Wear with Khakis ↓
Now that you know which colors to look for, let’s take a look at the best shoe styles to pair with your khaki pants.
Sneakers
We’ll start with the most casual style of shoe on our list, which is also one of the most versatile.
As mentioned above, khakis can be dressed up or down depending on the rest of your outfit, and sneakers are a great choice if you’re going for a more laid back and casual look.
If you’re wearing sneakers strictly for style reasons, you might opt for a minimalist pair, like the white leather pair listed below.
But depending on your body type and general level of health, you might want something more supportive and performance-focused from brands like Nike, Allbirds or Adidas.
Both types have their place and can work quite well with khakis, just remember to keep the rest of your outfit casual and relaxed.
Sharp Selections:
Boat Shoes
Named for their nautical origins, pairing boat shoes with khakis is a classic look that evokes the timeless style of John F. Kennedy.
(Or for a more modern example, the laid back cool of John Legend.)
Prototypical summer wear, boat shoes are a great alternative to flip flops because they pair better with pretty much every style of pants, including everything from khakis and chinos to shorts and skinny jeans.
Sharp Selections:
Driving Shoes
Driving shoes are casual loafers with a rubber sole, which helps your foot maintain a sturdy grip on the petal when you’re driving.
They’re similar to boat shoes in that they long ago outgrew their original purpose, and today are one of the best casual shoes to pair with just any type of pants.
And they’re a better option than boaters if you’re a city dweller, since they offer a lot of the same casual cool, but without the sea-based backstory.
Sharp Selections:
Crossovers / Hybrids
Just as khaki pants can be dressed up or down, crossover shoes – also called hybrids – are halfway between a pair of dress shoes and a pair of sneakers.
Up top they have the leather upper and sophisticated toe shape of dress shoes, but underneath is a padded footbed and rubber outsole that’s comparable to what you’d find on running shoes.
The result is a modern twist on a classic style that can work well with both formal and casual khaki looks.
Sharp Selections:
Check out our in-depth Wolf & Shepherd review to find out how their Swiftknit crossovers hold up under scrutiny.
The Best Boots to Wear with Khakis ↓
Chelsea Boots
Any type of ankle boots will give your khakis a more rugged look and feel, but chelseas are probably the most practical.
Unlike other boot styles, chelseas have elastic side panels that let them forego laces so you can easily slip them on and off.
The result is a boot that’s a lot more convenient than other dress boots, but doesn’t sacrifice anything in the style department.
Sharp Selections:
Work Boots or Combat Boots
And speaking of a great way to make your khakis look more masculine and rugged…
While any type of leather boots can lend your look a little toughness, work boots and combat boots are the most muscular (and tend to make you look the most bad-ass).
While combat boots can work great with slim-cut or even skinny khakis, work boots tend to be thicker around the ankles, so they usually work best with straight leg (or even wide leg) pants.
Sharp Selections:
Chukka Boots / Desert Boots
Quite possibly the most versatile pair of shoes or boots a man can own, chukkas look great with any type of pants—khakis very much included.
In fact, khakis actually harken back to chukka’s origins.
They were first worn by British soldiers during the desert campaigns of WWII – hence the name desert boots – when soldiers would pair them with their sand-colored uniforms.
So pairing your khakis with a good pair of chukkas is a great way to evoke our brave (and undeniably dapper) forebears, while simultaneously looking modern and masculine.
Sharp Selections:
For more stylish desert boots, check out our complete round-up of the best men’s chukka boots on the market.
The Best Dress Shoes for Khakis ↓
Now that you know which types of shoes work best for making khakis look casual, let’s take a look at a few models that will help you make them look more sophisticated and refined.
Combine any of the dress shoes below with a well-fitted pair of khakis, some dress socks and a slim leather belt for a look that’s polished, put-together and perfect for dressier occasions.
Cap Toe Shoes
Cap toe shoes aren’t a type of dress shoe so much as a style; any of the shoe types below can be found with a cap toe.
But they’re worth calling out cap toes separately because the (handsome) devil is in the details:
Sometimes standing out from the crowd means finding different ways to distinguish yourself from what all the other guys are wearing.
And opting for a great shoe with a handsome cap toe is a smart (if subtle) way to do just that.
Sharp Selections:
Check out our full Beckett Simonon review to see how their cap toe shoes held up after rigorous testing.
Monk Straps
Another great way to distinguish your dress shoes from the masses is to opt for monk strap shoes.
Instead of using traditional laces, these shoes use straps made from the same material as the rest of the shoe (usually leather or suede), which are then sealed with metallic buckles.
The hearty leather strap and the presence of a little metal lend monk straps a masculine look that’s still quite dapper and refined, which is perfect for khakis.
The most common variety is double monk strap shoes, which use two buckles, but single monk straps are also fairly common.
(Triple monk straps are rare, and in my opinion look a little too “busy” to truly work well with khakis.)
Sharp Selections:
Oxford Shoes
Arguably the prototypical type of dress shoe, oxfords are a great shoe to wear with a khaki suit (or just khaki dress pants).
Oxfords are distinguished by their closed lacing system, meaning the eyelets for the laces are sewn underneath the vamp (aka the upper portion of the shoe).
Burying the eyelets underneath gives oxfords a more minimalistic and streamlined design, and that simplicity is what makes them look more sophisticated than other shoe styles.
Sharp Selections:
Derby Shoes
If oxfords are the number one type of dress shoe, derbies are a close runner up.
The main difference between the two is that derbies have an open lacing system, so the eyelets are on the outside of the vamp.
This gives derbies a slightly more casual look, but it’s worth noting that there are a lot of other factors that can make derbies (or any dress shoe) look sophisticated.
As long as a shoe has a svelte toe shape – meaning not too round, but not too triangular and pointy – and a relatively thin sole, it can still look quite sharp.
So, Derbies are great shoes for teachers and other guys who frequently wear khakis in a business casual environment, but the right shoes can also be worn to most formal occasions as well.
Penny Loafers
Some people will dispute the idea that penny loafers are dress shoes.
But the great thing about pennies is that, much like khakis, they can be both formal and informal, depending on the factors mentioned above like toe shape and the thickness of the sole.
Suede loafers with a slightly more squared-off toe are perfect for casual khaki outfits, while a well made pair of leather pennies with a more sophisticated toe shape can easily be paired with a summer suit.
Sharp Selections:
Wingtips / Brogues
The word “brogues” refers to the small perforations you sometimes see in certain shoe styles.
They originated with English hunting parties from hundreds of years ago, when men wanted dress shoes with small holes in them so that water would escape the shoe when they traipsed through bogs and puddles.
As such they were traditionally considered a more casual style of shoe.
But today we live in an extremely casual world where men frequently wear sneakers to work and flip flops to the airport, so really any shoe that covers your toes and is made out of leather is pretty much a dress shoe.
Fortunately, the broguing on modern shoes is strictly decorative, and like a cap toe or a monk strap, the unique patterns add an extra dimension that can help your shoes stand out.
Sharp Selections:
Oh, one last thing…
The Best Color Socks for Khakis ↓
Since originally writing about the best colors and types of shoes for khakis, I’ve heard from a few readers who wanted to know what color of socks works best.
The debate about whether your socks should match your shoes or pants is one of the most contentious in menswear, but as far as I’m concerned, you basically have three options here.
Khaki Socks
First, you could go with beige or khaki colored socks.
Wearing socks that match your pants color is always a safe bet.
It’s also recommended to shorter guys as a little trick to make their legs look longer – and thus their frames look taller – since the same color will be maintained all the way from your waist to the top of your shoes.
Colorful Socks
The second option is to go with a color that either contrasts or complements your khakis, rather than matching them.
The classic move here is to match your socks to your shirt color.
But if you want to have some fun with it, you could also throw caution to the wind and opt for a fun multi-color pattern or design.
Khakis are a fairly classic (and in some people’s eyes, boring) pant style, so you might want to use your socks as a way to inject a little fun into your look.
Skip the Socks
Finally, if the weather’s warm, I highly recommend you skip the socks next time you wear khakis.
The sockless look is a carefree move that can add just a touch of roguish rebellion to an otherwise staid and traditional khaki getup.
But note that this really only works with low rise shoes.
If you’re wearing any of the boot styles above, you’ll definitely want to keep your socks on for the sake of both style and comfort.
More Resources ↓
More Advice on Men’s Boots and Shoes from Irreverent Gent:
- The Most Stylish Men’s Casual Boots to Wear with Jeans
- The (Absolute) Best Shoes for No Socks
- 9 Stylish & Comfortable Dress Shoes That Feel Like Sneakers
- The Absolute Best Men’s Shoes for Standing All Day
- The 25 Best Men’s Summer Shoes
- The 8 Most Stylish Types of Men’s Shoes
- The (Absolute) Best Casual Shoes for Men
- The Best Nursing Shoes for Men
- The Best Men’s Shoes for Plantar Fasciitis
- 17 of the Best Men’s Chukka Boots
- In Review: Beckett Simonon Shoes
- The All-Around Best Shoes for Retail Workers
- The 31 Best Shoes for Walking on Concrete All Day
- How to
WearRock a Blue Suit and Brown Shoes - The Most Comfortable Work Boots on the Market
- In Review: Thursday Boot Company’s “Captain”
- The 9 Best Boot Styles for Men
- The Most Stylish, Comfortable & Best Shoes for Male Teachers
- In Review: Johnston & Murphy Karnes Cap Toe Boot
- The 21 Best Shoes to Wear with Shorts
- In-Depth Wolf and Shepherd Shoes Review
- The (Absolute) Best Shoes to Wear with Chinos
- The 11 Most Comfortable Steel Toe Boots for Standing All Day
- The Best Shoes to Wear with Jeans
- The Best Italian Shoe Brands for Men
- The Absolute Best Shoe Brands Like Allbirds
Banner Image: Benjamin Rascoe / Unsplash | Illustration: Irreverent Gent
