How to Wear Chukka Boots: An EveryMan's Ultimate Guide

Elevating Style With Chukka Boots

Image Courtesy of Thursday Boots

They say that a man's shoes either make or break his outfit. Wise words that stay relevant even today. The reason is because shoes are an ending point of your silhouette, when someone first sees you, they look at your face, then they'll glance down at your shoes. Chukka boots, as you'll discover, are extremely versatile as they can be worn in a professional setting and are one of the best casual shoes for men when paired with jeans. 

As shoes are 1 of 2 ending points, it is the perfect place to signal:

  • You know what you're doing with your outfit
  • You know what you're doing and you have some personality

Get it right and draw comments (I know this from personal experience), get it wrong and turn a well tailored suit into a hot mess. 

Making or breaking an outfit

Left or right? 

Whether you're first starting out building a solid foundation of a wardrobe or you're looking for an upgrade, you need something that is stylish and functional. It is not just for show, but also not just for fashion. You need something that can work with many other pieces of your wardrobe. 

Our recommended choice is:

Chukka boots

The Chukka Boot!

Yes gentlemen I'm not recommending a dress shoe per se for your first dress shoe. Instead this is a dress boot. Here are some reasons why I recommend it:

  • Versatility: it can be dressed up or dressed down
  • Variety: They come in traditional calfskin leather, suede or synthetic.
  • In addition, colors give it even more variety (also excellent for summer).

For your first pair, its best to go with the most conservative design you can find. 

Chukka boots

Here are some key features to look for:

  • Dark brown
  • Thin sole
  • No embroidery on the upper
  • Sleek and refined appearance. 

Having said that, the chukka boot can be worn in a variety of situations. They can be worn with a casual jeans and t shirt outfit to step up your outfit, chukkas can be worn with chinos and dress shirt in those office settings. And if you are adventurous, they can even be worn with a charcoal or navy suit without garnering unwanted attention (I did this in my job interview with no problem!). Here are some examples of outfits that work with the chukka boot:

Chukka Boot Outfits

As you can see, you can dress it up with a suit and tie for a fresh modern look or you can dress it all the way down to t shirt and jeans in a manner that makes your outfit standout subtly without overdoing it. Whether you're going around town, to a wedding, a day in the office or an interview, chukka boots can be that finishing piece that you've been looking for. It works with virtually everything (within reason) and that is why it is such a go to piece. 

Wikipedia also has good information on the difference between Chukka Boots and Desert Boots. 

The Takeaway: If you want to upgrade your wardrobe, footwear is essential. Look no further than the chukka boot for your first upgrade as few other dress shoes/boots can match it in versatility and variations.


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