How To Wear Chukka Boots: 5 Different Outfits

by Beau Hayhoe  |  in Accessories

Looking for ideas about how to wear chukka boots? You’ve come to the right place.

For those times when a minimal white sneaker is too casual, and a leather dress shoe is too formal… chukka boots can be the perfect shoe to finish off your smart, sharp, casual outfit.

Follow Effortless Gent’s board Five Ways To Wear One on Pinterest.

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 the perfect example of a casual leather shoe. Great with jeans and chinos… but that’s about it.

The right chukka boot can do even more than meets the eye, however — it can be dressed up or down because of how it was designed.

Finding The Right Pair Of Chukka Boots

laval chukka boot in tan from Beckett Simonon
The Laval Chukka from Beckett Simonon

Picking the right chukka boot so you have a versatile shoe that can be worn with casual as well as dressy / business casual looks requires a few things:

  • a smooth, polished leather
  • a perfectly rounded toe (not boxy, not pointed)
  • blucher, or derby style open lacing
  • a stacked leather heel (vs a crepe sole, like the Clarks)
  • light to medium shade of brown (black feels too formal)

Given all those specifications, there’s one current favorite that nicely fits those criteria — the Laval Chukka from Beckett Simonon.

At $229, it’s a great choice if you want something that can go both casual and dressy.

For the sake of simplicity, we’ll use the Laval in our examples.

Beckett Simonon Laval Chukka

Whether you’re sporting your favorite pair of jeans or a sport coat and chinos, the Laval Chukkas have you covered. These are one of the few styles that ensure you’ll never be overdressed or underdressed.


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.

An affordable (yet highly regarded) option from Kiwi would be excellent. The gold standard as far as polishes go is this one from Saphir.

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.

Five Ways To Wear Chukka Boots

Without further ado, why don’t we get into the outfits?

1. Cold-Weather Business Casual

a business casual look with gray trousers v neck sweater and chukkas

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

a cold weather outfit with denim white henley grey overshirt and chukka boots

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 gives off rugged vibes compared to a simple plain long-sleeve T-shirt.

Combined with a grey shirt jacket, it’s an outfit with a lot of workwear-inspired mojo, which just seems 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 casual outfit with tan chinos short sleeve shirt and chukkas

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).

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

how to wear chukka boots casually with denim and a chambray shirt

It’s understandable that some might be hesitant to try out this outfit.

Vests, or waistcoats, are often overlooked, but they can definitely work in place of a blazer or cardigan and is great at cleaning up the lines of an un-tailored shirt.

You want to make sure you’re picking up the right vest, though. No smooth wools with a sheen—those typically belong with formal suits.

The texture of a wool vest not only brings down the formality, but is also more appropriate for cooler 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 helps to add even more texture.

5. The Dress Ensemble

how to wear chukka boots formally with a grey suit and light blue dress shirt

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…

A brown leather chukka boot is a solid Lean Wardrobe addition. It looks great with a ton of different outfits, not just the five I put together for you here. Plus, being able to dress them up and down make them a no-brainer.

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

Beckett Simonon Laval Chukka

Whether you’re sporting your favorite pair of jeans or a sport coat and chinos, the Laval Chukkas have you covered. These are one of the few styles that ensure you’ll never be overdressed or underdressed.


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This article was originally published in March 2014.