6 Types of Shoes that Go With Khaki Shorts with Photos

Summer is in full swing. The sun, the sand, the breeze – this is the perfect time to bust out your khaki shorts and enjoy a carefree day strolling around doing nothing and everything. Khaki shorts are lightweight and cooling – in short, the perfect pants for summer. Better yet, khaki shorts are a classic that transcends trends. You do not have to worry about being out of fashion. Khaki shorts are always in style. They are a no-brainer when it is hot outside.

What you do need to think about is what shoes to pair with your khaki shorts. Your shoes complement and complete your look. They help you to stand out from the crowd and to define your personal style. But there are so many choices for shoes that it can be overwhelming. No worries, we are here to help. We will show you the 6 styles of shoes that go well with khaki shorts. For each shoe style, our staff here at Love At First Fit has combed through the products on the market to come up with our top 5 picks for that style. Now your shoe choice can also be a no-brainer.

But first, we will take a brief detour and look at the history of khaki.


A Brief History of Khaki Shorts

Today, people commonly use the word “khaki” to mean a lightweight cotton twill fabric. But originally, khaki was a color, a light yellowish-brown hue that was similar to the color of the soil. The word khaki is a loanword from Hindustani, one that means “soil-colored.”

Khaki traced its root to the British Indian Army in the 19th century. At that time, British soldiers stationed in India were still wearing the traditional British uniform of white trousers and bright red wool coats (hence the famed moniker “Redcoats.”) However, that uniform became a liability in the scorching Indian summer climate. So, in 1848, the Britons decided to ditch their white trousers and red wool coats in favor of the local lightweight cotton garments. They also smeared their outfits with soil to create a camouflage. Khaki was thus born.

From its military origin, khaki found its way to the civilian world and eventually became a classic. Khakis are very versatile. Every man should have at least one pair of khaki pants and one pair of khaki shorts in his closet.


Shoes to Wear With Khaki Shorts

Both as a color and a fabric, Khaki is casual and informal. It is earthy, natural, and easygoing. So when choosing shoes to wear with your khaki shorts, avoid overly formal shoes such as Oxfords or monk straps. Go with something more relaxed.

Related: What Shoe Look Good with Red Dresses? Examples with Photos

In the following sections, we will look at the 6 styles of shoes that go well with Khaki shorts. To save you even more time, for each style we have also combed through the offerings on the market and come up with our top picks. No matter your taste and style, we hope you will find something you like here.


Loafers With Khaki Shorts

The first loafer was created in the 19th century in London by the bespoke shoe company Wildsmith Shoes as a house slipper for King George VI. From its royal British origin, loafer spread first to Norway and then to the rest of Europe. Eventually, loafer crossed the Atlantic and took root in America. In the 1930s, a shoemaker in Maine invented the penny loafer, which quickly became an icon of preppy style.

If you like the preppy look, wear penny loafers sock-free with crisp khaki shorts, a buttoned down shirt, and a blue casual blazer.

Suede tassel loafers will also look good with khaki shorts and a simple white shirt.

Our Loafer Top Picks:

Cole Haan Men’s Nantucket Loafer II

On Sale
Cole Haan Men's Nantucket Loafer, British Tan Handstain, 10
  • 100% leather nantucket loafer has been a huge success since its introduction...
  • With nearly 80 years in the business and hundreds of points of distribution in...
  • Founded in 1928 as a collaboration between trafton Cole and Eddie haan, Cole...
  • Number of pieces: 1

ALEADER Men’s Canvas Slip-On Loafer

ALEADER Mens Slip On Shoes Casual Canvas Sneakers Summer...
  • Fabric upper and Rational design create a comfortable and breathable fit
  • Slip-on design and dual side goring make for easy on and off
  • Upgraded anti-skid durable rubber soles,lightweight and easy to walk
  • Padded insole provides great comfort and high resilience

Skechers Men’s Superior Milford Slip-On Loafer

On Sale
Skechers USA Men's Superior Milford Slip-on Loafer, Light...
  • Casual loafer featuring dual-goring insets and rear heel-pull tab

Crocs Men’s Santa Cruz 2 Luxe Loafer

crocs Men's Santa Cruz 2 Luxe M Slip-On Loafer,...
  • KEEP IT CASUAL: The same Crocs Santa Cruz Men's Loafers with some updates inside...
  • MEN'S BOAT SHOES: These are the boat shoes men need, offering a modern...
  • SINK-IN SOFT: With the softest footbed yet, these are the loafers men need with...
  • LONG-LASTING: These men's slip on shoes offer comfort that will last, mile after...

Sanuk Men’s Vagabond Slip On

On Sale
Sanuk Vagabond Brindle 10 D (M)
  • Sized appropriately to meet the needs of the Big & Tall
  • Canvas upper with frayed edges on a wider profile slip-on construction
  • Soft canvas lining. Fit tip- Fits true to size
  • Premium, molded eva footbed featuring an antimicrobial additive designed to...

Chukka Boots With Khaki Shorts

Just like khakis, Chukka boots originated in the British military. They were the desert boots worn by the British soldiers in the North African Campaign of World War II.

Chukka boots are ankle-length boots with leather or suede uppers, leather or rubber outsoles, and open lacing with two or three pairs of eyelets. They are typically casual footwear but some Chukka boots with glossy leather uppers and leather soles can also be quite dressy.

With khaki shorts, go with Chukka boots that are more informal. A pair of sand-colored suede Chukka boots with rubber soles would look great with khaki shorts and a white v-neck t-shirt.

Another great combo is chocolate-colored Chukkas, brown khaki shorts, and an olive long sleeve t-shirt.

Our Chukka Boot Top Picks:

Clarks Men’s Bushacre 2 Chukka Boot

On Sale
Clarks Men's Bushacre 2, Beeswax, 10.5 M US
  • The finish or polish on these boots show marks which are not scratches
  • Chukka boot silhouette , Two eyelet lace-up front , Cushioned insole
  • Upper material - suede. Lining material-leather
  • Note:Color shade may vary due to lighting

UGG Men’s Dustin Chukka Boot

UGG Men's Dustin Chukka Chukka Boot, Chestnut, 10
  • Soft suede upper
  • Treadlite by UGG outsole for comfort and durability
  • EVA insole with textile lining

Nunn Bush Men’s Lancaster Plain Toe Chukka Boot

On Sale
Nunn Bush mens Chukka Boot Lancaster Plain Toe, Brown, 9.5...
  • CLASSIC STYLE: The Nunn Bush Lancaster Plain Toe Chukka boot features a choice...
  • COMFORT: Designed with a memory foam insole to cushion your every step. This...
  • PERFECT FIT: Adjustable three eyelet lace up closure ensures perfect adjustment...
  • OUTSOLE: High quality and long wearing outsole that provides a durable grip on a...

Clarks Men’s Stinson Hi Chukka Boot

On Sale
Clarks Men's Stinson Hi Chukka Boot,Sand Suede,9.5 M US
  • The heel height is 1.25 inches and the upper material is suede

Dockers Men’s Greyson Leather Casual Chukka Boot

On Sale
Dockers Mens Greyson Leather Casual Chukka Boot, Black, 8 M
  • Genuine leather uppers
  • Comfort Zone Technology with two zones of comfort
  • A cushioned sponge EVA heel pad for added support and breathable footbed for...
  • Footbed treated with Cleansport NXT: A hygienic technology that provides odor...

Sneakers With Khaki Shorts

Sneakers are the ultimate streetwear shoes. Whether they are performance sports shoes from Nike and ASICS, or casual footwear from adidas and Converse, or designer creations from the likes of Prada and Dior, sneakers can amp up the cool factor of any outfit. Not to mention, sneakers are also very comfy.

For a retro look, pair Converse Chuck Taylors with khaki shorts and a vintage t-shirt. For a more adventurous look, go with adidas Marquee Boost and a printed casual shirt. Want maximum comfort? Try any ASICS Gel running shoes.

Our Sneaker Top Picks:

Converse Men’s Chuck Taylor Sneakers

Converse Chuck Taylor All Star Seasonal Colors Ox Unisex (44...
  • 100% Textile
  • Imported
  • Rubber sole
  • Shaft measures approximately low-top from arch

ASICS Men’s Gel-Venture 6 Running Shoe

On Sale
ASICS Men's Gel-Venture 6 Running Shoe, Black/Phantom/Mid...
  • Rearfoot GEL Cushioning System: Attenuates shock during impact phase and allows...
  • Removable Sockliner: A sockliner which can be removed to accommodate a medical...
  • Removable Sockliner: A sockliner which can be removed to accommodate a medical...
  • Trail Specific Outsole: Reversed lugs provide uphill and downhill traction on...

adidas Men’s Marquee Boost High-Top Fabric Basketball Shoe

Nike Men’s Air Max Torch 4 Running Sneaker

PUMA Men’s Suede Classic Plus Sneakers

PUMA Suede Classic Sneaker,Black/White,11 M US Men's
  • Suede sneaker with Formstrip overlay featuring lace-up vamp and padded collar...

Boat Shoes With Khaki Shorts

Boat shoes, as their name implies, are designed for use on boats. They typically have canvas or leather uppers with non-marking rubber soles. A siping pattern is cut into the soles to provide traction on wet decks.

Boat shoes were invented in 1935 by American sailor and inventor Paul A. Sperry. One day while sailing, Sperry slipped on the deck of his boat and fell overboard. Fortunately, he was able to get back on board. This accident spurred him to work on developing a non-slip shoe just for boating. One day, he noticed his dog was able to run over ice easily without slipping. Inspired by the grooves on his dog’s paws, he used a knife to cut a herringbone pattern into his shoes’ soles to increase traction. The result was the first modern boat shoe. He founded a company named Sperry Top-Sider to manufacture and sell his invention.

While initially worn mainly by sailors, by the 1970s boat shoes have become casual footwear worn everywhere. The rugged look of boat shoes fits particularly well with khakis.

To play up its nautical heritage, wear boat shoes with a blue striped t-shirt, a navy blazer, and a pair of khaki shorts. Or go all preppy by pairing navy boat shoes with white khaki shorts and a salmon polo shirt.

Wear your boat shoes either without socks or with no show ankle socks. The key is to keep your ankles bare.

Our Boat Shoe Top Picks:

Sperry Men’s Authentic Original 2-Eye Boat Shoe

Sperry Mens A/O 2-Eye Boat Shoe, Sahara, 10
  • Leather boat shoe featuring moccasin-stitched toe, rust-resistant eyelets, and...
  • Genuine hand-sewn Tru-Moc construction for durable comfort
  • Non-marking outsole with wet/dry traction
  • 360 degree lacing system

Columbia PFG Men’s Bahama Vent PFG Boat Shoe

On Sale
Columbia Men's Bahama Vent PFG Boat Shoe , Waterproof &...
  • ADVANCED TECHNOLOGY: Men's Bahama Vent PFG Boat Shoe Wide features our...
  • HANDY FEATURES: Days out on the water are comfortable and worry-free with this...
  • ADJUSTABLE FEATURES: This boat shoe features a lace-up closure for an...
  • VERSATILE STYLE: This men's waterproof boat shoe delivers style and durability...

Sperry Men’s Halyard Sneaker

Amazon Brand – 206 Collective Men’s Boat Shoe

206 Collective Men's Boat Shoe Tan 9 Medium US
  • Genuine Leather Upper
  • Rubber Cup Sole
  • Non Marking

Dockers Men’s Beacon Boat Shoe

Dockers Men's Beacon Boat Shoe, Tan/Taupe, 11.5 W US
  • Genuine leather uppers
  • Treated with NeverWet, a revolutionary water and stain guard that instantly...
  • Double goring on each side for an easy slip on and off the foot
  • Footbed treated with Cleansport NXT: An anti-microbial technology that provides...

Espadrilles With Khaki Shorts

Espadrilles are casual, flat shoes with a canvas or cotton fabric upper and a sole made of esparto rope. The esparto rope sole is what makes a shoe an espadrille.

The first mentioning of espadrilles dates back to at least 1322. Back then, espadrilles were peasant shoes made in the Occitania region of France and all over Spain.

From its root as a peasant footwear in Europe, espadrille has become a popular casual shoe all over the world. Its earth-tone canvas upper and distinctive rope-based soles make it a perfect shoe for summer.

Wear a pair of striped espadrilles with pastel khaki shorts and a plain t-shirt. Or a pair of color-block espadrilles with sand khaki shorts and a white linen shirt. You will look like you have just stepped out of a Mediterranean island vacation commercial.

Our EspadrilleTop Picks:

TOMS Men’s Alpargata Rope Loafer Flat

Alexis Leroy Pureness Textile Men’s Flat Espadrilles

On Sale
Alexis Leroy Casual Stripe Men Espadrilles Flats Blue Stripe...
  • Slip-on Style
  • Round Jute-capped Toe
  • Light weight and construction with elastic V-panel for easy on and off all-day...
  • Quality Breathable Mesh Upper

Soludos Men’s Dali Canvas Slip On Espadrilles

No products found.

Starella Men’s Espadrilles

Men's Stripe Espadrilles Flats Driving Loafer Smoking...
  • Breathable canvas upper. Linen insole.
  • Natural rubber antiskid outsole.
  • Elastic bungee at both sides is easy for you to slip on.
  • Pleather floding at front and back collars make the shoes more comfortable,...

Havaianas Men’s Origine Stripes Espadrilles, Blue

Havaianas Men's Origine Stripes Espadrilles, Blue, 10 US
  • Havaianas Blue Origine Stripes Espadrilles
  • Brand New and Genuine. We are an authorised seller of Havaianas.
  • See product description below for more information.

Sandals With Khaki Shorts

Sandal is the oldest type of shoes anywhere. The oldest sandals were discovered in Fort Rock Cave of Oregon, US. They are made of sagebrush bark and are at least 10,000 years old.

When wearing sandals with khaki shorts, go with sandals that are less bulky and more breezy. Pair brown sandals with pale blue khaki shorts and a plain t-shirt to cool down on a hot summer day, and enjoy the breeze on your feet. Life does not get much better than that.

Our SandalTop Picks:

Rainbow Men’s Leather Sandals

Rainbow Sandals Single Layer Premier Leather Men's Sandal...
  • Single Layer Arch
  • Embossed Rainbow Logo
  • Double Stitched
  • Nylon Toe Piece

Reef Men’s Cushion Bounce Phantom Sandal

Reef Men's Cushion Phantom Sandal, Black, 10 M US
  • THE ONLY SANDAL YOU NEED: When beach sandals and ultimate comfort come together,...
  • DURABLE + COMFORT: Phantom flip flops have padded jersey lined straps that have...
  • CUSHION BOUNCE TECHNOLOGY: Reef Signature Cushion Bounce sandals have a high...
  • NO BREAK-IN PERIOD: Packed with the comfort and support of Reef's anatomical...

Vionic Unisex Wave Toe-Post Sandal with Concealed Orthotic Arch Support

Vionic Unisex Wave Toe Post Sandal, 9 B(M) US Women / 8 D(M)...
  • Nylon Webbing Upper. EVA Footbed. Durable Rubber Outsole.
  • EVERYDAY SUPPORT: A podiatrist-designed footbed built into every pair of Vionic...
  • YOUR NEW FAVORITE SANDALS: Our unisex toe-post sandal features soft nylon...
  • If you are a half size, we recommend ordering the nearest size down. Fits medium...

Quiksilver Men’s Carver Nubuck Sandal

On Sale
Quiksilver Men's Carver Nubuck Sandal, TAN/Solid, 9
  • Vegan and water friendly
  • Arch support, heel counter collapsible toe post

Oakley Men’s Supercoil 2.0 Sandals

Oakley Supercoil Men's Sandal (USA Print)- Size 14.0
  • Providing all-day comfort for warm-weather excursions, the Super Coil 2.0 Sandal...
  • Built to help keep you moving naturally on a variety of surfaces–from sand to...
  • The comfortable strap features an American Flag design within our iconic Oakley...
  • 100% Polyester

Key Takeaways

Before you go off to find your perfect shoes to wear with khaki shorts, just keep a few key things in mind:

  • Khakis are casual and informal. They are best worn with informal shoes. Avoid overly formal shoes such as Oxfords or monk straps.
  • Khaki shorts go well with loafers, Chukka boots, sneakers, boat shoes, espadrilles, and sandals.
  • Feel free to experiment with color and texture. The key here is to find your own voice and your own style. Make something uniquely yours.

Happy shopping and happy summering!

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Last update on 2020-11-20 / Affiliate links / Images from Amazon Product Advertising API