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    Home»Fashion»Part one, a brief history – Permanent Style
    Fashion

    Part one, a brief history – Permanent Style

    Decapitalist NewsBy Decapitalist NewsMay 21, 2026007 Mins Read
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    Part one, a brief history – Permanent Style
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    In a two-part series beginning today, Tony readies himself (and us) for summer with a look at the enduring style of the CVO shoe. In part two he will give an overview of his favourite contemporary models; today he looks at the history, pinpointing when the canvas sneaker became the leisure footwear of choice for a burgeoning middle-class.

    —

    By Tony Sylvester.

    “Booth’s houndstooth, cut for his father on Savile Row by Huntsman during the Battle of Britain, was pinched at the waist; the boy rescued his presentation from foppery with a black knit tie and faded blue canvas Top-Sider sneakers, spattered by specks of bronze boat-bottom paint.’”

    – Geoffrey Wolff “The Final Club”

    It was a long winter down here on the coast. Interminably grey flat skies punctuated with false springs that got chased off after a couple of hours. No storms, no snow, just endless drizzle and sunless vistas.

    Now the sun has come out, the big coats have gone back into the under-bed storage boxes, and I’m minded to take stock of my summer wardrobe.

    A couple of years back, I penned a little piece here at PS Towers reflecting on interwar style on the French Riviera; how the expats and emigres brought a new style into being, creating the very idea of a summer season in the process. 

    Simon followed up with more specificity, laying out some practical options for sartorial holiday-making, and there’s one particular item I wanted to revisit and hone in on: the rather mechanical sounding Circular Vamp Oxford, or CVO for short.

    It was a very dashing photo of David Niven (shown top) that prompted a deep dive. Snapped in 1956, one hand on the handle of his Bentley S1 Continental Coupe, Niven is the epitome of that Riviera elan I spoke of in the earlier article. 

    Pale odd jacket with contrasting double pleat trousers, dark shirt and wide striped repp tie, all atop a pair of canvas shoes with distinctive rubber soles. The image is made all the more powerful by the exact echoing of the outfit to the motor: the two-tone Bentley astride whitewall tyres. He couldn’t have planned the shot any better if he’d tried.

    The history of the canvas and rubber shoe goes back a century before that to the introduction of the ‘Sand Shoe’ from the Liverpool Rubber Company. As the name suggests, it was designed as a beach boot, to accompany the brand’s full range of overshoes, ‘wellies’ and other rubber goods.

    At the end of the 19th century, rubber coat magnate Charles Mackintosh bought the company and amalgamated it with John Boyd Dunlop’s eponymous brand. In the 1870s Scottish inventor Dunlop had patented the pneumatic tyre and together they brought the world a low top proto-sports shoe in the same canvas and vulcanised rubber, quickly dubbed ‘the Plimsoll’ by the British public. 

    The trademark dark line around the white rubber sole mimicked the safety line for loading goods painted onto the side of ships, brought about by MP Samuel Plimsoll in 1876’s Merchant Shipping Act. A century later, British school-kids still referred to any white canvas sports shoes as Plimsolls; not sneakers, trainers or tennis shoes.

    Although these new innovations seemed perfect to mirror the emerging pastimes and activities, it took a while for these canvas and rubber creations to be adopted by sportsmen at the more aristocratic end of the spectrum. In fact, thanks to the benefit of the men’s fashion press of the time, we can almost pinpoint the exact moment. 

    American trade magazine Apparel Arts’ Summer 1932 ‘Fashion Forecast – Shoes’ features a two page spread of suitable footwear for gentlemen of leisure (above). Yachtsmen are advised toward white buckskin derbies with rubber soles; budding tennis players toward two tone ‘sports shoes’ – Goodyear welted toe caps in brown calfskin and white canvas – “widely accepted for torrid weather by international sportsmen”. 

    The closest we come to an all-canvas number is the summer espadrille whose form and function differ greatly, a topic suitably covered by Manish in a previous post. Glossy ads for Conrad Shoe Co and Friendly Five Shoes back this up with their white, cream and two tone leather or suede offerings; perforated leather and “flexible” soles their only concessions to sportiness.

    The following year’s summer guide is a different story however. “Activities of the Summer Months – As Observed by Apparel Arts” features a series of illustrated fellows decked out in their finery. The tennis chap is resplendent in ribbon trimmed blazer, spotted muffler and white flannels and “white canvas shoes with crepe soles”. Jackpot. 

    The introduction of Esquire Magazine in the autumn of 1933 heralds the first time these illustrations and guidance were made available to civilians outside of the menswear trade, and again, summering gents are drawn atop canvas shoes. 

    “Court Costume For The Season Of 1934” (above) reports on “white canvas sneakers” despite noting that “Cuban Jai Alai shoes are smarter in appearance”. “On The Trail Blazed By Bunny Austin” from 1935 reports on said English tennis player’s influence, pointing out that alongside “white sneakers”  are “new blue canvas sneakers that have been taken up by many well known professionals”. Canvas sneakers had arrived in the country clubs and resorts of the high and mighty.

    At the same moment, amateur sailor and duck-decoy inventor Paul Sperry falls arse over teakettle on the deck of his schooner, ending up overboard in the rarefied drink of Long Island Sound. This starts him thinking about the possibility of a non-slip shoe. 

    Inspired by the sight of his cocker spaniel’s ability to remain upright in the icy conditions of Connecticut winters, Sperry experiments with cutting patterns into the bottom of rubber soles, emulating the rough leather of his dog’s foot pads. 

    By 1937, he has sold his patent for non-slip soles to the Converse Rubber Company, ensuring they manufacture the herringbone patterned ‘siped’ soles for him exclusively and the ‘Top Sider’ is born, proving an instant hit with his fellow members of the Cruising Club Of America. 

    By 1939, the United States War Department made a deal to supply the canvas shoe to its sailors (above), and it became a crucial piece of working kit and an official part of the casual uniform of the US Navy. Post war, the yachting connection remains strong. How many summer fit moodboards don’t contain at least one photo of JFK aboard his boat ‘Manitou’, shaggy dog sweater, ray bans and white Top siders all present and accounted for?

    Simultaneously, the US Rubber Company’s brand Ked’s launch The Yeoman (above). The company had been making athletic shoes with such Olympian names as ‘Triumph’ and ‘The Champion’ since 1916, but the Yeoman is fascinating to me as it appears to be the first canvas shoe marketed strictly for leisure rather than sport. 

    Its inspiration is clearly a series of canvas and crepe walking shoes that Edward Windsor was fond of. In the famous photos of his wardrobe and shoe racks, you can see them lined up on the bottom row, tan derbies on red rubber (below). 

    Accepted wisdom has them as bespoke creations from a London shoemaker, but origins remain opaque. Keds spun an entire line of footwear from this model which remained in their catalogue for at least the next two decades; a wonderful embodiment of the midcentury middle classes’ aspiration to leisure. Adverts see them accompanying beach visits, BBQs and lawn mowing.

    I first became aware of them long after the fact. By the 1980s, the shape was borrowed by cheap shoemakers in Asia, sold back to the US under the brand name Zig Zag.

    Affectionately named as ‘Winos’, they became prison issue in the California penitentiary system, and sported by Mexican gang members and musicians. You can see them in cult gang films Colors (1988), American Me (1992) and Blood In Blood Out (1993), in the street portraits by Meririck Morton, and on stage with Venice crossover legends Suicidal Tendencies. All of these elements would be a big wardrobe inspo for me. 

    Talking of wardrobes, I’ve heaved my shoe boxes out from the dark corners, and in part two we’ll have a look at some of the contemporary options that keep the same spirit alive.



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