CVO Shoes: From Boats to Boards and Beyond

Man wearing cut-off chinos and off-white Sperry CVO shoes
Image is my own / All rights reserved

Sperry shoes (which I wrote about earlier this week) are all but synonymous with the iconic, best-selling boat shoe design that is the leather Top-Sider. But while the brand’s invention of the modern deck shoe is pretty well known, there is another Sperry shoe design that hasn’t gotten quite the same recognition, despite predating the more famous Top-Sider and being arguably comparable in terms of influence.

I’m thinking here of the Sperry Cloud CVO, which, unless you’re either well-acquainted with the Sperry catalogue or a real menswear diehard, might not be a name that sounds all that familiar. You will, however, almost certainly have seen the actual shoe it describes. ‘CVO’ stands for Circular Vamp Oxford, which isn’t exactly an inspired title but does a decent job of describing the shoe’s key features. The CVO is, indeed, a spin on the traditional Oxford shoe design and is characterised by a single piece of material that sweeps along the vamp (i.e. the front of the shoe) all the way around and into the shank within the shoe’s footbed, resulting in a roughly circular shape. They also have quarter panels on either side, rubber soles, and cotton uppers that come in a range of colours, though off-white, navy blue, and washed red have long been especially popular.

If you’d like to know more about the development of the Sperry CVO, check out the article I published earlier this week or one from last year on the subject of boat shoes. It’s a good story which I go into in some detail in those pieces, but what I’m more concerned with here (for fear of unnecessarily repeating myself) is the legacy of the CVO after Sperry put it out into the world. 

Henri Cochet wearing CVO shoes 1922
Image credit: Bibliothèque nationale de France / Public domain

But first, a further note clarifying some terms: We already know that CVO means Circular Vamp Oxford, but it’s worth dwelling on the fact that Sperry’s own labelling of the product has changed somewhat over time, which can be confusing especially to a contemporary audience. When these canvas deck shoes first came to market in the 1930s, Sperry simply referred to them as Top-Siders, in reference to the topside or deck of a boat. The brand’s marketing materials stuck to this nomenclature for decades to come, even after the release of the better-known leather version of the Top-Sider (also known as the Authentic Original, or AO for short). At some point, however, the model got renamed the Cloud CVO (it’s officially listed as the ‘Unisex Cloud CVO Deck Sneaker’ on their website today), perhaps because ‘Top-Sider’ came to refer in common parlance more specifically to the CVO’s moc-toed, leather counterpart. Moreover, just as ‘Top-Sider’ has turned into something of a generic term for ‘boat shoe’, so too ‘CVO’ has become broadly used to describe this style of canvas shoe even when it isn’t made by Sperry.

Okay, with all of that hopefully cleared up, let’s return to the main drag. 

Sperry created the CVO design in 1935. With quick-drying cotton uppers and grippy, non-scuffing rubber soles, it was purpose-built for sailing. The design was quickly adopted by the maritime set, first within Sperry’s yacht club and via mail order, then soon after by retailers like Abercrombie & Fitch. Within just a few years, these canvas boat shoes become part of the US Navy’s standard issue during WWII courtesy of a deal struck with Sperry shortly before America entered the war effort. As the century progressed they also caught on among the collegiate set, such that by the 1960s CVOs had become one of the most versatile shoe options in the prepster arsenal since they paired well with everything from tailoring down to jeans, chinos, and shorts. They also proved popular in broader sporting contexts like tennis, surfing, and skateboarding. 

It’s from within this latter subculture that the other famous CVO emerges in the form of the Vans Authentic, which, along with the subsequent Era model, is arguably the better-known version of this shoe style today. Although Vans in some sense represented the West Coast’s answer to Sperry (which hails from New Haven, Connecticut), the brand’s founder was also born on the East Coast in Braintree, Massachusetts in 1930, just five years before Sperry’s CVO came into the world. What’s more, he spent his early years working for a local rubber company that made canvas shoes. When he eventually moved to Anaheim, California, and opened his own shoe store his plan was to sell quality shoes at a low price. In doing so, he succeeded in undercutting Sperry’s original CVO price some thirty years after the fact. The first pairs of Vans Authentics (then known simply as #44 deck shoes) sold for $4.49 a pop in 1966, while a 1935 pair of Sperry’s would have set you back $4.50. A pair of women’s Vans, meanwhile, went for just $2.29.

White Authetic Vans shoes dangling over a city skyline
Image credit: Nathan Ziemanski on Unsplash

Of course, Sperry and Vans are by no means the only games in town. Keds, for example, have been making their similar-looking Champion model since as early as 1916, while countless other canvas shoe purveyors have their own versions, including long-established names like Converse and Jack Purcell, as well as more niche brands like Doek and Common Projects.

I’ve been wearing CVOs of one kind or another since I was a teenager and have never been without a pair in the intervening years. It seemed an obvious fit since so many of the cultural figures I idolised back then wore them, like David Byrne in Stop Making Sense or Robert Shaw, Richard Dreyfuss and even a behind-the-scenes Steven Spielberg in Jaws. As the years went by I realised how often they appeared on the feet of style icons like Paul Newman, Steve McQueen, Rock Hudson, and Humphrey Bogart. Later still, as menswear progressively became a professional interest, I always took note when I saw them being worn by contemporary menswear figures like cartoonist Dick Carroll, author Simon Crompton, or vintage dealers Sean Crowley or Brian Davis.

Not long ago Robb Report described CVOs as being to sneakers ‘what Levi’s 501s are to denim: the purest, simplest classic’. They are also just as versatile since, like 501s, they fit comfortably in the oft-opposing worlds of prep, workwear, and streetwear. And just as I would never willingly go without my most reliable pair of jeans, so too I’ve never been without a trusty set of CVOs. I currently own two pairs, a set of OG Sperrys and some Authentics from Vans’ Vault collection. But if my history with canvas shoes has proven anything, it’s that, not unlike a good pair of jeans, you can really never have enough. Luckily for us, there are just shy of a century worth of CVOs out there to choose from — all you need to do is hop on board.

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