Staple #25: The Chukkas

This Staple is sponsored by Wolverine. To purchase the shoes featured in the post, head over here.

A man’s shoe game is a tough detail to dial in. However, it’s also one of the most critical. Far too many stylish ensembles are ruined by the wrong pair of shoes. While we’ve already covered our bases with what a man should look for in his dress shoes, there’s one particular type of casual footwear that should be in every man’s wardrobe.

Wolverine Orville Chukka

Chukkas (along with their name) originated from the sport of polo. They’re an ankle boot with two or three eyeholes that can be made from any material. Dressier chukkas will have full-grain or top-grain leather while more casual versions are made with suede.

Another common, but not always applicable, name used is desert boots. It’s kind of like all squares being rectangles but not all rectangles are squares. A desert boot is a chukka but it’s one that made the transition from British WWII military life to the civilian world. The defining characteristic is a chukka with a crepe rubber sole.

The beauty of chukkas is in their simplicity and versatility. They can be worn on a date, to your kids’ soccer game, while working in the garage, bar trolling with friends, to the movies, or anywhere but the most formal situations or the beach. Dressier versions can even be worn in an office or business environment during cooler months.

Chukkas are so timeless and so simple that they transcend age as well. They still look young and unique for a kid in junior high or high school and the retirement-age Baby Boomer can wear them to look more intentional and put together than his Seinfeld-sneaker-wearing peers.


My own experience has taught me that they’re ideal for traveling too. A few weeks ago my wife and I spent a long weekend in the Bay area with two of my brothers and their wives. Because of the airline we flew and the short time of the trip, we packed incredibly lightly – only leaving room for one pair of shoes.

Grabbing these chukkas was an easy choice. They looked great when we were sight seeing, at church, out to dinner, and hiking in the Redwoods. Not only did they look good, but they were functional and comfortable. Many shoes get heavy or irritating after walking for miles on end or spending an entire day on a bicycle – these however held up to the use, looked great, and my feet weren’t begging me to take them off as soon as we got in each night.

One of the best and most common uses of a desert boot is to dress down a High/Low look.

High/Low Date Night

Shirt and Jacket by Beckett & Robb, Square by Declan, Jeans by Koben, Shoes by Wolverine

By throwing them on with some dark jeans, an OCBD, and a patterned jacket, it’s possible to look distinguished without taking life too seriously.


This is an ideal outfit for any time a casual first impression is key. Wear it out at night, to that office party, or on a first date. An outfit like this works any time of the year as long as the jacket is swapped out for something that is seasonally appropriate.

Shovel-Head Balancing Champion

Shirt by Frank & Oak, Vest by Buffalo Jackson, Jeans by Koben, Shoes by Wolverine

Of course, going to the opposite end of the spectrum works just as well. These are my go-to kicks when I’m out running Saturday errands, visiting my in-laws, helping a friend move, or practicing the soon-to-be Olympic sport of shovel-head balancing.

Wolverine 1883 Orvilles Milkshake

The relationship of form and function means they can be worn in an environment too rough for dress shoes or even non-boot casual shoes, without looking like a construction worker. Remember, these things were worn by the military in some pretty adverse conditions.

Spring Style

Henley by Urban Outfitters, Jacket by Zara, Cargos by Levi’s, Shoes by Wolverine

They’re also an excellent way to tone down a trendy outfit. While I’m an advocate of classic style, there’s room to embrace trends in bits and doses.

These slim cargos will not be cool in a couple of years. They’ll look outdated and probably a bit silly. But it’s a fashion that’s going strong right now and can be fun. The key is to pair them with timeless classics like a baracuta jacket and desert boots as a way to anchor it all down.

Wolverine 1883 Orvilles

While some companies can skew too dressed up or too casual with their chukkas, I’m a big fan of the Orvilles by Wolverine. They strike the right balance of stylish, usable, and comfortable. They’re also made to Wolverine’s exacting standards and come in at a fraction of the price of lines like their 1000 mile. They’re a great way to try out a brand with a long, well-earned heritage without spending an arm and a leg.

Two words of caution with any pair of chukka – don’t wear them in formal situations. Yes dress versions can be worn in business settings, but these are not shoes to be worn to funerals, job interviews, or black-tie events. Also, they can be worn with shorts, but it comes off as a bit Bohemian. Plan accordingly or avoid pairing them with shorts and things will be fine.


 As always, I want to give a heartfelt thank you to Chad Keyes. Chad reached out to me a little less than a year ago and has been the man behind all of the great images in three of the four most recent staples. If you’re ever in need of a photographer, he’s a blast to work with, has the right balance between directing and observing, and obviously does an excellent job, so send him some love.

Meet The Author

Tanner is the founder and primary author of Masculine Style. He lives in Salt Lake City, Utah with his wife and two kids, and helps run Beckett & Robb - a men's clothing company built around custom suits and shirts.
  • Clint Barton

    Great article on the chukkaas, Tanner. I’ll definitely look into getting something more on the dressier side for this spring/summer.

    I’m not a big fan of the desert boots anymore. I bought some Clarks a few years back to wear with shorts but they wern’t that comfortable, they seemed floppy around the ankle where the pants/jeans hit, and it was hard to get a good fit with only two eyelets on them.

    Keep the staples coming!

    • MasculineStyle

      Thanks Clint. I have a dressier pair that I love wearing with suits or as a way to dress up my High/Low stuff.

    • M.

      I didn’t like Clarks, either; same complaints. Perhaps you’d like John Varvatos’ version that I found better. 3 eyelets and the ankle was better for me. I have this version I got from a Nordstrom Rack: http://www.ebay.com/itm/John-Varvatos-Star-USA-Hipster-Chukka-Boot-Olive-Green-Suede-Size-8-5-M-/231162154872 – this is not my listing. The grey suede version is currently on sale for $99 from JV. OR you can sometimes find them in Racks for $69.

  • Brian

    One of my favorite things about your articles is how you explain the history and evolution of an item of clothing. This always helps me put it into context in deciding whether it is appropriate in a given situation, because normally (as you explain) the history still dictates – to some degree – how formal or informal it is, or how rugged/rakish/refined it is.

    Anyway, glad to see that here again, in another great post.

    • MasculineStyle

      That’s exactly why I write the history. Glad it’s having the intended effect.

      • Brian

        If you haven’t already written a post taking about the origin or appropriateness if corduroy, I’d be interested to read one. If you have, what is the title? I’ll search for it.

  • Dman

    Thanks. I have been looking for something like this. Bought a pair of the Albert’s from Wolverine.

    • MasculineStyle

      Hope you enjoy them. Both of my Wolverine’s have been great kicks.

  • carlos

    Great post! What color chukkas look better for summer casual and easier to match with summer-colored clothes: light grey, tan, or some other color?

    • MasculineStyle

      Lighter is typically better in the summer. Both a light grey and a tan will be equally versatile.

      • carlos

        Thanks! BTW, I have some brown Ecco Turn Gore-Tex Chukkas that I wear to work or in dressy casual situations on rainy or snowy days and they work great. They go with just about anything, as you said.

  • John

    For some reason I was under the impression that chukkas were seasonal. You can wear these year round?

    • MasculineStyle

      It really depends on the chukka. Suede versions are better if they’re not worn in snowy or heavy rain, but any other leather type is fine even in those conditions. I’d definitely consider these an all-season shoe.

  • SH

    You look like Andre Schurle, the German football player!

  • Matt

    Digging the beard dude! Looking beastly

    • MasculineStyle

      Thanks Matt. I feel like a Viking. It’s almost long enough I can braid it.

  • http://www.wellbuiltstyle.com/ WellBuiltStyle

    I was never a huge fan of the slim cargo trousers that have become so popular over the last year or so. Probably because I haven’t seen someone pull them off quite as well as you just did. I’m taking notes. Well done!


    • MasculineStyle

      It’s definitely a hard trend to wear right. Most guys either go too baggy or too skinny. That or they try to dress them up too much.

  • Reggie Carroll Jr.

    Great article bro…besides Wolverine (who’s Chukka’s look great by the way), what other shoe companies do you consider to engineer a excellent to at least decent pair?

    • MasculineStyle

      Thanks Reggie. The classic Clarke’s desert boot is a great go-to for a classic chukka.

      • Reggie Carroll Jr.

        Thanks a lot bro!! Stay sharp! Lol

  • Reggie Carroll Jr.

    Also with Autumn on the way…and Winter on its heels…what would make for a versatile grouping of colors?

    • MasculineStyle

      Earth tones. Anything that’s considered an autumn shade will be warm, rich, and fairly saturated.

  • T H

    Hi Tanner,
    Considering the differences between a normal chukka and a desert boot(crepe sole), can a desert boot also be worn with the same versatility as a chukka without a crepe sole?
    Just bought the original clarks desert boot(crepe sole) :)
    Hope to hear from you soon!
    T H

  • Dantes

    Hi tanner,

    Thanks for all the great tips. What color are your Orville’s by Wolverine – Moss Green or Milkshake?

    • http://masculine-style.com Tanner

      Glad you liked the post. Mine are the milkshake.