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.

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

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

Looking for classic, open chukka-style lacing (as opposed to the closed lacing of this boot) 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.

A bit of burnishing at the toe is slightly more casual, too. Make sure the toe stays rounded, as opposed to boxy.

Given all those specifications, there’s one boot that nicely fits those criteria — this option from Steve Madden.

At $125, it’s a tad pricier than the Clarks version, but would go with more dress and casual looks overall. Catch it on sale, and it might fall below $100.

(Editor’s Note: If you’re curious about other options, here are a few: one, two, three, four. For the sake of simplicity, we’ll use the Steve Madden chukka in our examples.)

Shop EG’s Chukka Picks on Amazon


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.

Now, on to the looks!

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 banded 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 popover shirt, as discussed in an earlier post on dark denim, is an awesome alternative to a traditional polo or even a T-shirt. The popover’s collar is just slightly different from a normal polo, yet the light and airy fabric combined with the small print on this shirt provide a good amount of visual interest.

If you’re into the whole ‘air tie’ look, those three buttons could be buttoned up if you feel particularly adventurous. Sizes are slim in that size at the moment, but the general idea in terms of color and fit should stay the same if and when it gets back in stock.

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

As far as that item goes, JackThreads (aff link) is a decidedly trendy, street style site and yet does feature some nice items at low prices. 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 in the photo linked to above.

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.

That grey flannel suit is certainly pricey, but other grey suit substitutes are available from places like Alfani RED. As far as the overall outfit goes, we’ve definitely seen that boots are becoming more and more acceptable to wear with all manner of 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 flannel 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.

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PUBLISHED March 27, 2014

A Michigan State University alumnus, Beau works in the fashion division at New York City's Coyne PR. In addition to writing for Effortless Gent, Beau's menswear writing has appeared on Dappered, VOUCH Mag, and GearHungry. He also runs his own blog, The Style Guide.

  • Sal

    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.

    • Noted! Bet that felt good, didn’t it?

  • John Armstrong

    really surprised you use Steve madden as an example given the numerous complaints about quality ….

    • Bo

      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.

    • 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.

  • Dominic

    Sneakers can be worn to not look “sloppy”. Are you saying to NEVER wear sneakers period?

    • Bo

      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!

  • erasmus portugal

    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

      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.

  • Scott

    Would “Timberland Earthkeepers® City Lite Chukka” work? Or are they too casual to be dressed up?

  • Scott

    Any minimalist or 0 drop chukka’s out there?

  • LegalEagle

    I personally use these Steve Madden boots $50, comfortable, and looks great. Keep up the great work gents!

  • LegalEagle

    I personally use these Steve Madden boots $50, comfortable, and looks great. Keep up the great work gents!

  • LegalEagle

    I personally use these Steve Madden boots $50, comfortable, and looks great. Keep up the great work gents!

  • I know this article is a few months old, but as of today the Steve Madden Bronxxx linked above is on sale at for $79.90. Just an FYI!

  • cfheld

    Worst ideas of the decade:

    1. ISIS
    2. Twerking
    3. Ludlow suit

    Man that thing looks awful.