Chukka Boot Guide featuring Beckett Simonon

Happy New Year! Welcome to 2019 as I begin this year with a blog post about yet another one of my favorite topics: SHOES! Have you ever worn a pair of Chukka boots? They’re one of the few popular styles that have become iconic with trend today. Well, for those of you who either love Chukkas or are not familiar, I partnered with Beckett Simonon once again to give you a quick guide to this awesome form of boot.

1) History

There is speculation of where the boot really originally derived from, but many sources say that the term “chukka” came from the sport of polo. Polo matches consisted of 4-8 chukkas/chukkers who wore boots similar to Jodhpur boots (which resembled Chelsea boots). Fast forward to the period of WWII where soldiers would wear a variation of Chukka boots known as the desert boot. “Rather a leather sole, these boots featured rubber soles for better traction in the desert terrain” (source: Poppy Barley).

The footwear brand Clarks made desert boots mainstream and they have evolved to what they are today. I found this history super interesting!

Sources: Gentleman’s Gazette, Poppy Barley

2) Suede vs. Leather

Without relying too heavily on outside sources for this part, I wanted to provide a couple thoughts about wearing suede & leather Chukkas.

I’ve seen that suede Chukkas have become very on-trend. My recommendation would be to dress down with suede Chukkas and dress up with leather Chukkas. You can probably get away with wearing business casual clothes with suede, which wouldn’t look too bad, but I’d rather go with leather for work purposes.


3) Style Recommendations

I love Chukka boots year round. They are especially good in the fall and winter when it gets gloomy or rainy because I treat them like any other boot. Here, I’m rocking the Laval Chukka Boots by Beckett Simonon. I mentioned earlier that I like wearing leather boots for work, so I styled myself a little more professional here. However, if I were wearing suede Chukkas, I’d wear chinos and a cardigan. Other style recommendations:

  • Leather chukkas with chinos and a blazer (not full suit)

  • Leather chukkas with dress pants, vest, and t-shirt

  • Suede chukkas with jeans and long sleeves


If you’re considering a new pair of dress shoes or boots, definitely check out Beckett Simonon. What’s cool about these Chukkas is that they are comfortable and are able to conform to to different conditions, both socially and environmentally. The traditional rubber sole has been switched out for a single layer leather sole for lightness and flexibility. And, a thinner welt adds an element of sleek elegance. The Ellis resembles a dress Derby that can be worn with more looks than a traditional Chukka. Be sure to use code SOOR20 for a 20% discount on their website!

Photography by Danny Nieves