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.

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