As important as it is to maintain versatility and quality on the top part of your body, it’s just as important to to look for that same versatility in your footwear.

Enter: Chukka boots. This can be a tricky piece to master — you want to do a couple things with the right, versatile piece of footwear.

Stay away from athletic sneakers outside of the gym lest you look sloppy, but avoid getting too dialed up with something like a shiny black patent leather shoe (like one that would go with a tuxedo).

In the middle of that spectrum are other pitfalls, too. You obviously want to avoid the clunky, square-toed casual/dress hybrid shoes. So what other choices do you have?

That’s where the ultra-classic chukka boot comes in.

The chukka is both classic and modern at the same time. Clarks has been making a staple version of the boot for years, and that style is practically the perfect template for a casual shoe.

The chukka boot can do even more than meets the eye, however — it can be dressed up or down just as ably as any other shoe, especially when worn with a dressier sole than the Clarks crepe sole.

Finding A Pair Of Chukka Boots

cole haan chukka boots


Picking the right shoe to meet that dressy/casual hybrid involves a few things.

Looking for open chukka-style lacing as this keeps the shoe more casual-leaning. And something in a nice, medium shade of brown is also much more casual than a shade of black, so look for that color.

Make sure the toe stays rounded, as opposed to boxy.

Given all those specifications, there’s one boot that nicely fits those criteria — the “Barron” (ha!) chukka boot from Cole Haan.

At $200, it’s a great choice if you want something that can go both casual and dressy.

Editor’s Note: If you’re curious about other options, here are a few:

For the sake of simplicity, we’ll use the Cole Haan chukka in our examples.

Care For Your Chukka Boots

Caring for this shoe is essential to keep in mind, as well.

That leather starts out awfully shiny, but getting these shoes beat up a bit (just a bit — don’t go mud-bogging with this pair now) isn’t the end of the world. Keeping them in prime condition, however, will be key to extending their durability.

Shining your shoes is going to be the first step after especially heavy wear. Be sure to look for a shade of polish that fits with the shade of the shoe.

A cheap (and yet highly-regarded) option from Kiwi would be excellent. There are also varying recommendations on how to care for shoes that might point you in the right direction, too.

Goes without saying: If you go with a suede option, you don’t polish them. Simply go over with a horsehair brush to take care of the nap and get any surface-level dirt out.

Now, on to the looks!

Five Ways To Wear Chukka Boots

1. Cold-Weather Business Casual



The shirt pictured above is a bit more of an eye-catching, trendy piece than a classic item like an Oxford cloth button-down or a shirt with a simple stripe or plaid pattern, but it’s a refreshing way to mix things up when going without a tie.

You can also wear a blue-hued patterned shirt with this darker blue sweater if you wanted; it would help the shirt to pop just a bit.

Because those trousers have a slight herringbone stripe to them (and because of the sweater), this outfit is perfect for a business-casual look in the cold weather that’s still dressed up a touch.

And the anchor of the whole piece? A classic chukka boot silhouette that retains some nice polish and sheen. Pair it with a crisp dive watch to complete the entire polished (but not too dressed-up) ensemble.

2. Winter Weather Casual


In a casual cold-weather situation (or even just a time when there’s a bit more chill in the air than normal), a henley, especially one with some thermal insulation, is a rugged, masculine pick worn by nearly everybody.

There’s just something about that band collar and placket that looks more durable and rugged than a plain long-sleeve T-shirt (although that could be layered under here as well).

Combined with a grey shirt jacket, it’s an outfit with a lot of workwear-inspired vibes, which just seem to go well with something as timeless as a chukka boot.

Using two somewhat unconventional items on top stands in contrast to the nice dark blue denim, allowing you to experiment more with texture on the top half.

3. Spring Weather Casual


A slim, short sleeve oxford button down collar is an awesome alternative to a traditional polo or even a T-shirt. The trick is to find one that is fitted, not huge and billowy (avoid that Dwight Schrute office worker look). The seafoam green color on this shirt provides a good amount of visual interest.

Because the shirt stands out a bit more in terms of color, go with a safer (and yet still slim-cut) tan chino on the bottom.

The great thing about those same chukka boots is that they’re slick enough to go with a nice pair of chinos (thanks to the leather sole, as opposed to a crepe soled desert boot), and yet the open lacing keeps them casual.

4. Mixing Textures & Fabrics


It’s understandable that some might be hesitant to try out this outfit. Vests have a very costume-like, Western vibe, yet in a slim fit, it can work just as well as a blazer or cardigan at cleaning up the lines of an untailored shirt, as Joe from notes over here.

And on some guys, a vest just works. This outfit takes away from some of the novelty of a shiny silk vest by downgrading that texture to something more appropriate for colder climes. If the vest is too much however, a v-neck sweater could easily be swapped in.

The chambray shirt, with its rougher fabric, pairs very well with a less dressy vest.

In keeping with the changing texture of the outfit, a more casual knit tie is the better bet than a silk tie. If you so desire, ditch the tie and wear the shirt open, a la Brandon Flowers.

Once again, the dark denim and chukka boots anchor the outfit, and a braided leather belt could again work in terms of adding some texture.

5. The Dress Ensemble


Utilizing the same navy knit tie from The Tie Bar as used above, this outfit turns heads because of the subtle tweaks it makes on the traditional ensemble.

As far as the overall outfit goes, we’ve definitely seen that boots are becoming more and more acceptable to wear with suits, particularly when it’s a bit colder outside.

We’ve also seen it used in particular by everyone’s favorite secret agent, providing as great a barometer of the style world as any. This case is no different, except these boots are brown, not black.

When taking something as simple as a grey suit and a light blue dress shirt (keep that fit slim!), use a slightly more unconventional navy knit tie, a pocket square with a small pop of color and those boots to breathe some life into the outfit.

In conclusion…

With a chukka boot like this one, the potential for various outfits is almost limitless given the right dose of creativity and a good regard for using (and occasionally breaking) style fundamentals.

Like the other items in your Lean Wardrobe, take good care of these shoes and you’ll be surprised how far they might take you.

Cole Haan 'Barron' Chukka Boot via Nordstrom Price: $139.90 Cole Haan 'Barron' Chukka Boot via Nordstrom

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19 Responses

  1. Sal on

    A desert boot is a two-eyelet suede chukka with a crepe sole. What you show here is a regular leather chukka boot. This is just lazy.

    • Bo on

      Hi John — let me jump in on this one (as the author!). I’ve had my pair of those Steve Madden boots for a little over a year, and while trekking through the snow across campus in Michigan hasn’t done them any huge favors, they’ve held up more than alright with polishing, care and rotating them in and out with other pairs of shoes. I realize that everyone has different experiences with shoes, however, but I’ve found mine to be more than serviceable for the price. They’re not Allen Edmonds or anything, but they do alright for a college kid! Thanks for reading, btw.

    • Barron on

      I also provided other examples above, at different price points, if Steve Maddens aren’t your thing. I’m not a fan of most of their shoes (at least the ones I’ve seen) but these look decent, and if you can get them for a deal, they would do as a budget shoe. As Beau says, they’re no AE or Alden, but decent for a guy on a budget or still figuring out if a chukka is his thing or not.

    • Bo on

      Hi Dominic — let me clarify what I wrote up there. I mentioned to preferably stay away from athletic sneakers outside the gym (something like a pair of Nike running shoes), but I’m definitely all for wearing classic casual sneakers in the right situation (something like a plain plimsoll or a canvas sneaker definitely goes great with jeans or a slim pair of shorts and a pocket tee, for example). Thanks for reading!

  2. erasmus portugal on

    I love my boots! I use them for everything because it just looks so good the awesome caramel color. Everybody comments on them! Also because it’s hard to find in my city. That said, it is a bit (very) dirty and I’m afraid to ruin the leather because I already tried to clean them once and it made it a bit lighter and lost its shine. So I really need advice on how to clean them without ruining them.

    • carlos on

      I use Kiwi saddle soap to clean my leather shoes. I know some people say saddle soap is too rough for shoe leather but I’ve never had any problems.

  3. Brian on

    The english shoe makers like Church’s and Crockett & Jones make some fantastic chukka boots in calf, suede and even cordovan leathers. These will cost a little more but will last a lifetime if taken care of as they can be repaired back at the factory by replacing soles and heels when worn down. I have a few pairs and are my go-to casual footwear for most occasions in winter and summer


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