Moments In Time – World War II Military Sneakers

Moments In Time is a new series exclusive to our Heddels+ community. In this series, we will take a closer look at specific pieces and silhouettes from the past which have had a lasting impact on our niche today. From unsung-but-iconic vintage pieces like the Cossack Jacket and Karakoram Parka to modern heritage staples like the Guayabera shirt and Monkey Boot, we’ll be dissecting these classics to find out how they made their mark and where we can find both vintage and contemporary articles today. 


There are plenty of trends that began in the military that have reverberated into everyday dress – arguably serving as the foundation for Americana. Whether it’s denim, white undershirts, chambray shirts — or even leather jackets — the influence on GIs coming home after the war had a huge effect on how they dressed and therefore how those around them began modeling their style. But one style cue you might not have expected to hail from time overseas is casual footwear. No, not boots and oxfords, but actual sneakers as we know them today!

Sneaks. They’re the Swiss army knife of your wardrobe pulling in any direction you need them, whether you’re trying to collect some style points or need something reliable on your foot, all without taking yourself too seriously. And although they’re commonplace in the streets, on the court, and anywhere else a ‘no shoes, no service’ sign might be applicable, one place you might not have expected them to play a significant role in, is the military. And yet, it makes sense. In fact, some of the earliest examples of sneakers were worn by soldiers while training and serving in the military.

And not only were these grandfather models crucial for combat training and beyond, but they would also go on to become templates of modern-day sneaker styles. So, if you’re wearing their spawn, isn’t it about time you learned a little more about the family tree?

What Styles Are We Talking About?

Coming in multiple styles over the course of several wars, two distinct vulcanized models emerged and went on to become staples in the “fabric” of casual dress throughout the decades.

The first is what I would describe as a high-top training sneaker. Think 1940s basketball sneaker — and if that means nothing to you –think a pair of Converse Chuck Taylor high tops but just a little different and a little antiquated. Coming in black or olive green, they featured a rubber sole and toe-box and were made with a canvas upper. They’d have a slightly structured heel cup, sometimes a reinforced stripe around midway through the upper, and often had vertical ribs around the toe.

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Image via Worth Point

The second model is the Deck Shoe issued to the US Navy. Pictured below, it featured a white canvas upper and black rubber sole, sometimes with a black rubber toe cap. Think your basic low-top canvas deck sneaker/pumps – Keds, Vans, Sperry both USN models were stripped-down archetypes that were meant purely for functionality. The canvas was hardwearing and quick-ish drying, the rubber was resistant and flexible, but the package, — when all tied up  — also turned out to be extremely timeless.

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Image via Segui Riveted

Although the styles couldn’t get any simpler in terms of footwear construction, there was some major elegance happening. And though both styles existed before WWII, perhaps even dating back to WWI in some capacity, their largest impact and archetypal construction patterns came during the Second World War.

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Image via The Real McCoy’s

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A Pair of USMC “Jungle Shoes” via Lot-Point

Who Was Making Them?

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USMC 1944 Contract Converse Sneaker via Us Militaria Forum

Like most things being manufactured during WWII, lots of makers had their feet in the door one way or another, so it’s hard to really pin down loads of on-point examples. But that’s part of the point I guess – these aren’t the types of items that are defined by the manufacturer- they’re defined by the circumstances and context of why they were made. But if we did have to narrow it down, Converse for the high-top training shoe and Sperry for the deck shoe are lay-ups. But US Rubber Co, Ball Band, and Keds were all brands likely in the mix as well.

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A pair of WWIIWomen’s US Army Sneakers produced by Endicott Johnson in 1945, via The Rite Stuff

How Much Will An Original Pair Set You Back?

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A pair of 1940s WW2 Converse Chuck Taylor All Star USMC Hi-Tops, sold for $630 on Etsy

But what happens when your interest in these kicks extends beyond this article and the internet and you’re you actually want a pair of OGs? Well, even more so than regular vintage items, vintage footwear as you might assume, is pretty difficult to come by because they were one garment you could guarantee got worn hard. Remember this is pre-sneaker head culture (pre being super precious about any article of clothing), and when you factor in that these were military-issued pieces of footwear and the likelihood of them surviving just got lower. Lastly, let’s talk about what happens to rubber over the years when left sitting for decades. It gets warped. It hardens. It flakes, leaving a bread crumb trail of black gold as you walk down the street.

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A pair of original USMC sneakers, available for $370 from Etsy

Remarkably, after this gauntlet of unfavorable odds, authentic examples do pop up from time to time ranging from display only to dead stock, mostly in smaller sizes though. But they’re out there and the usual reselling sites like Worthpoint, as well as Instagram an Etsy, are your best bet to track down a pair. If you’re really serious, perhaps a military show is a good lead. Then again, after you pay that end of rainbow price, trust me, you’ll be tip-toeing everywhere you go, afraid of cracking them, getting them scuffed, and hoping the sole doesn’t peel off with every step. So let’s try to save you from the rollercoaster of emotions with some nice modern iterations.

Where To Buy Today

That’s right! As usual, going the repro route is probably your best bet. Though, even then, faithful reproductions aren’t as easy to come by. Much harder to find than say, WWII-inspired of raw denim jeans. But I think that will change and more brands will produce them as people catch up. because these are types of sneakers that go with everything and have a look that while simple, just blows out any competition in their path.Truly the perfect compliment for heritage jeans, khakis, fatigues, or anything else that you’d want to pair them with.

The Real McCoys Military Canvas Training Shoes

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Available for $256 from Lost & Found

US Rubber Co High Top Sneaker – Military

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Available for £80GBP (~$95USD) from American Classics

Artifact By Superga 2435-MS Japanese Canvas High
Artifact By Superga 2435-Ms Japanese Canvas High - Triple Black

Available for $119 from End Clothing

Anatomica x Wakouwa Deck Shoes

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Available for $175 from Clutch Cafe

The Real McCoys USN Cotton Canvas Deck Shoes

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Available for $275 from The Real McCoy’s London

Pras Shellcap Low Sneakers

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Available for $133 from Redcast Heritage