These Are the Best Chukka Boots to Wear With Shorts

best Best Chukka Boots

Photo by Josh Sorenson

If you’ll be serving us leg goals, then we understand you’re probably in search of the best kind of shoes to match your shorts with. If you’ve decided to break out of the bandwagon of sneakers + shorts, to join the stylish group of chukka boots + shorts, then we have this to say to you: Attaboy!

You’ve made the right choice, and we want to help you make things easy. In this article, we share the best 5 chukka boots to wear with shorts, how to style your chukka boots with shorts, factors to consider when buying chukka boots, amongst other things you’ll find useful.

But first…

Can You Wear Chukka Boots with Shorts?

Absolutely. Chukka boots can be worn with shorts. I know you’re probably used to matching your shorts with sneakers. But you need to try matching them with chukka boots to see the switch a nice pair of chukka boots can provoke.

When it comes to men’s shoes, Chukka boots is the code word for adaptable and versatile. They are comfortable, stylish and can be paired effortlessly with both casual and smart wears.

A nice pair of chukka boots is just what you need to enunciate your charming legs. But be sure to moisturize properly so the exposed skin on your legs doesn’t get dry, especially during the dry season. (You can read our guide on body lotion)

There are different designs and colors of chukka boots to pick from. However, some chukka boots will make you look more stylish in your shorts than others.

Don’t worry, you don’t have to ransack the internet or stores looking for them. We’ve done that for you and we’ll be sharing the top 5 on our list in the next section.

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The Best 5 Chukka Boots You Can Wear With Shorts

1. The Red Wing Heritage Work Chukka

Red Wing Men's Heritage Work Chukka Boot, Briar Oil Slick, 7 D(M) US

Red Wing Heritage is a major stakeholder in the fashionable men’s boots industry. They pride themselves in crafting footwear that lasts.

These chukka boots are made of 100% leather with rubber outsole (which have a firm grip with the ground, reducing your chances of slipping).

We checked out what other customers said about these boots, and we noticed you’ll need to give it some time to break in to enjoy it better. (Most boots need time to break in.) If you’re looking to achieve a casual look, these boots are just what you need.

Main features

  • 100% leather
  • Rubber Euro-traction tred outsole
  • 4 inches shaft height
Buy on Amazon


2. Clark’s Bushacre 2 Chukka Boots

Best Clarks Men's Chukka Boots to Wear With Shorts

Think Clark, think ageless quality.

Clark’s Bushacre 2s are a pair of solid boots, that can be used for both formal and casual purposes. Its uppers are made of suede, and its lined with leather.

With time, you may notice that the area on the upper that folds when you walk will change to a lighter color. But that’s not much of a challenge as it can be fixed with a suede polish.

You can get these boots in different colors. Check out the size chart before ordering, so you get the right fit.

Main features

  • Leather lining
  • Synthetic sole
  • Upper material is suede
  • 2 eyelet lace-up
Buy on Amazon


3. Steve Madden Men’s Harken Chukka Boots

Steve Madden Men's Hestonn Chukka Boot,Tan,11 M US

Want to make a statement without speaking? Let Steve Madden men’s Harken chukka boots do the talking for you. Don’t stress.

If you have narrow feet, then you want to invest in these chukka boots.

The soles are triple-layered for your comfort and safety. This is the kind of chukka boots you wear only on special occasions that creates a lasting impression. It’s made of 100% leather and comes in different colours.

Most customers liked that the boots are comfortable. However, some people complained that the boots feel tight. That’s why we earlier recommended it for people with narrow feet.

Main features

  • Synthetic sole
  • 100% leather
  • Textile lining
  • Blind eyelet lacing
  • Shaft height = 3.5 inches
Buy on Amazon


4. Clark Men Stinson Hi Wallabee Chukka Boots

Clarks Men's Stinson Hi Chukka Boot,Sand Suede,9.5 M US

“These boots are made for walking,” wrote a delighted customer. A single glance at these boots can confirm this statement.

There are several reasons over 81% of 3,397 customers gave these boots a 5-star rating! If comfort is your buying guide, then you want to buy these pair of Clark’s Wallabee Chukka boots.

It has a shaft of 4 inches, so we’ll advice you wore these boots with a pair of socks to reduce friction. These boots are easy to maintain and will look great on you with an ultra-casual and casual outfit. You can shop for any colour of your choice available in Clark’s catalog.

Main Features

  • 4 inches shaft
  • Leather
  • Crepe sole
  • 25 inches heel
Buy on Amazon


5. London Fog Men’s Belmont Chukka Boots

LONDON FOG Mens Chukka Boot to wear with shorts

These boots break the norm of chukka boots, both in design and make, and we love it! Well, we’re not surprised. They are made by London Fog. A company reputed for its embodiment of classic metropolitan appeal.

You’ll surely get more compliments than you can reply with these boots. It’s not hard to tell why: these boots have a unique design. The counters and pull loops are made of leather a different color from the other parts of the boots. They are also arguably water-resistant boots, thanks to the denim they are made of.

Main Features

  • Memory foam insole
  • Dual colored
  • Made of denim
  • Synthetic soles
  • Water-resistant
Buy on Amazon


How to Style Chukka Boots with Shorts

Yes, we know. Wearing shorts makes your dressing almost irredeemably casual. But as with fashion, a little tweak here and there and you’ve created something new. In this section, we’ll see how to achieve 3 different dress codes with our chukka boots and shorts. They will depend on 2 major factors

– The material of the shorts and

– The shirt

1. Ultra casual

T-shirt + jean shorts

For an ultra-casual look, pair your chukka boots (like the Clark men Stinson Hi Wallabee) with a t-shirt and jean shorts. A face cap on a sunny day or a pair of sunglasses will look nice on you. For the ultra-casual effect, don’t tuck in.

2. Casual

Polo + chinos short

Got a rendezvous at the restaurant with colleagues on a hot day? You can wear your chukkas with chinos shorts and a polo shirt. Tuck in or don’t. That’s your call to make.

3. Formal

Formal shirt + cotton shorts

To achieve a formal look, match your boots with cotton shorts and a formal shirt. The shirt could be long or short sleeve. Add a fedora hat and tuck in your shirt for effect. If you’ll use a belt while at it, remember your belt should match your boots in colour and texture.

Factors to Consider When Buying Chukka Boots

  1. Flex point

The flex point of your shoe is where it bends when you walk with it. Your feet bend at the toes, so should your boots. If they don’t, you risk sustaining an injury.

2. Toe box

The toe box of a shoe is where your toes occupy. There should be enough room in your toe box. ½ inch to 1 inch of toe room is recommended. Wearing chukka boots with tight toe boxes can cause bunions, corn, hammertoes and other toe deformities.

3. Width

The width of your boots will determine if you’ll enjoy wearing your boots, or if every step you take will increase your chances of developing a foot deformity.

Boots don’t stretch much. So a tight boot in the store will remain a tight boot, no matter how long you wear it. It could even become tighter, considering that our feet swell slightly towards the end of the day.

4. Heel

A little heel slippage is permissible and advised for a new pair of chukka boots. By a little, we mean ¼ to ½ inches space. This is needed so the boot doesn’t feel too stiff.

Once the boot breaks in, this will be fixed. Just give it 1 – 2 months.

Related Questions

Are Chukka Boots Good for Walking?

First, let’s consider what makes a shoe fit for walking.

A walking shoe should be lightweight and offer good shock absorption. Its soles should cushion and support your foot and arch while you walk, and there should be enough space in your toe box to prevent calluses.

Chukka boots offer these securities. So, yes, chukka boots make good walking shoes as long as you buy the right size.

What is the difference between Chukka Boots and Desert Boots?

While chukka boots have hard thin leather soles, desert boots are characterized by soft thick rubber soles.

A little history, gentlemen;

Desert boots were originally designed for the British soldiers fighting in the desert during World War II. They needed a shoe that had a firm grip with the ground and could keep sand out of their feet. The chukka boot came through, but a few modifications had to be made to make it the perfect choice. These modifications gave birth to desert boots.

How Should Chukka Boots Fit?

We understand that boots need some time to break in before they become a perfect fit. But we should keep in mind that boots don’t stretch much, unlike other footwear.

With this in mind, it’s advisable to wear thick socks while testing your boot before buying. While testing your chukkas, the width should fit comfortably against your foot.

Care to know more about boots? You can check out our resource on 7 Best Men’s Boots for Everyday Wear or 5 Best Men’s Fall Winter Boots this Season.


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