How to Wear the Versatile Suede Chukka Boot

Chukka boots (also called chukkas) are some of the most versatile shoes a man will ever own, and they're one of my personal favorite types of boots.

This post will show you three ways to wear suede chukkas.

How to wear suede chukkas

Note: Big thanks to Thursday Boot Co. for hooking me up with a pair of their water resistant suede boots and for sponsoring this post! You can shop their entire collection at

First things first: what are chukka boots, and what's the difference between chukkas and desert boots?

Chukkas vs. Desert Boots

A chukker is a period of play in the sport of polo (you know, that game where rich British folks ride around on horses with long mallets and try to hit a little wooden ball into the opposing team's goal).

Chukka boot characteristicsThe name “chukka” is most likely derived from the word chukker, and it really just refers to the form of the boot, rather than the materials or construction.

Chukkas always have these three characteristics:

  • Ankle length
  • Open lacing
  • 2 or 3 pairs of eyelets

Desert boots are a specific type of chukkas worn by British soldiers in North Africa during World War II. They had crepe soles and soft suede uppers.

In the 1950s, the UK shoe company Clarks introduced the infamous Clark's Desert Boot, inspired by the boots British soldiers were bringing home from, well, the desert.

These days, people use the names “chukka” and “desert boot” interchangeably. I usually just call any type of ankle length boot an ankle boot to avoid confusion.

How to Wear Chukka Boots

Chukkas range from very casual to somewhat dressy. I like chukkas that hit that sweet spot right in the middle, like The Scout from Thursday Boot Co.

Types of chukka boots

J. Crew >> Thursday Boot Co. >> Alden

This means you can wear them in casual, business casual or – my personal favorite – smart casual settings.

I'll give you an example of each from my own wardrobe, starting with the most casual. And just for fun, let's do it #outfitgrid style!

Outfit Idea #1: Casual

It doesn't get much more basic than jeans, t-shirt and button up. This is a casual, comfortable getup that's perfect for every season except summer.

Casual chukka outfit

flannel | t-shirt | jeans | boots | watch | sunglasses | wallet

The standard choice of footwear for this getup would probably be white sneakers. But upgrading to midnight suede chukkas makes the whole outfit much more refined and unique.

You could throw on almost any piece of outerwear with this getup – a leather jacket, field jacket or even a parka.

Outfit Idea #2: Business Casual

Want to make your office uniform less boring? Swap out the ubiquitous brown leather bluchers for a pair of handsome suede ankle boots.

Business casual chukka outfit

jacket (similar) | shirt | chinosboots | sunglasses

If you wear this outfit to the office, I can almost guarantee someone will compliment you on your taste in shoes. If the midnight blue is too far outside your comfort zone, cognac is a safe alternative.

Outfit Idea #3: Smart Casual

Smart casual outfits are increasingly popular. In fact, experts believe this hybrid dress code will eventually replace business casual entirely.

And by experts I mean myself.

And by believe I mean hope.

Smart casual chukka outfit

cardigan | flannel | jeansboots | watch | sunglasses

The ankle boot is to smart casual what the Oxford is to formal. It's a perfect fit. Casual but not sloppy. Dressy but not formal.

A smart casual getup like this one is especially easy to put together during the cooler months when you actually have to wear layers to stay warm.

About Thursday Boot Co.

Thursday Boot Co. strives to make boots that have the durability of work boots and the sophistication of fashion boots.

Thursday Boots construction materialsIn other words, they want their boots to look great, feel comfortable and last a long time. To that end, they use premium quality materials and construction techniques, such as:

  • Leather from the Horween tannery in Chicago
  • Cork bed midsole that molds to your foot
  • EVA comfort strip (shock absorber typical found in athletic footwear)
  • Studded rubber outsoles (non-slip)

Founders, Nolan and Connor, aim to fill a void between hardcore work boots (that tend to be pretty heavy and bulky) and fashion boots (that are either super expensive or cheaply made – think YSL and H&M).

Brock wearing Thursday Boots

Wearing the President in brown | See this outfit

Some of their boots are made using WeatherSafe suede, which is actually water resistant. I like wearing suede shoes all year round, so this is a huge selling point for me.

I can't tell you how many times I left my suede shoes at home because of a slight chance of rain. Even worse, I've been caught in the rain wearing suede boots, which resulted in ugly watermarks and stains.

Of course, I haven't worn my chukkas in the rain yet, and like all boots, only time will tell how they hold up.

But based on my experience so far and because of the style, value and durability that Thursday Boot Co. offers, I give them two enthusiastic thumbs up.

Thursday Boots = Modest Man approved

Which outfit was your favorite? Let me know in the comments below!

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  1. Brock.
    I like outfit # 3. And I’m pushing the smart casual in any situation. I really like the blue suede boots. They provide a smooth connection to my dark jeans. I’ll be checking out Thursday Boot to order a pair of chukkas.

  2. Wolf reyes says:

    Love the 3rd outfit , although I don’t think the cardigan in the picture and the one you linked are the same which is unfortunate. But thank you for sharing Thursday boots I’ll definitely be getting a nice pair of chukkas there !

  3. I like outfit # 1 and #3. Love the boots. Some day I hope to get a pair.

  4. Hi Brock I’m an avid fan of yours. Just a quick question what are your thoughts on Chelsea boots for shorter men? (I’m 5’3 140lbs) I’m worried that in general they not in proportion with height

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