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Every year, I always feel the need, even before summer ends, to start shopping for something new to wear to all the festivals and fashion shows that appear on my work calendar each September. Usually, my hope is to find a seasonless piece, which designers are increasingly working into all of their collections, during the summer sales. A few weeks ago, while I was visiting Toronto from New York, where I live, I hit exactly that sort of jackpot.

The prize: a black Roland Mouret dress, which I discovered at The Room after considerable foraging through the Carvens, Erdems and Rodartes. When I slipped on the Mouret dress, my friend Nicholas Mellamphy, The Room's buying director, immediately voiced his approval. "It's very Jackie Kennedy," he said.

The simple, knee-grazing number, which has long, slim sleeves and a sexy second-skin fit, is a tad retro. Yet it is also utterly au courant. Its refined timelessness is, in fact, the shape of things to come, if the growing prominence of a new group of style icons is any indication. These New Classicists, as I call them, are high-profile, faultlessly groomed fashion professionals embracing the kind of classically chic clothing that Halston created for Jackie Onassis in the 1970s and YSL couture fan Nan Kempner always favoured.

Among them is Phoebe Philo, the Céline designer who is pushing this brand of polished ease perhaps more than anyone. Since her September, 2008, appointment as creative director of the venerable French house, continuity has defined her collections. Rather than innovate season after season, Philo tweaks a group of core staples that are based on her own everyday wardrobe. "There's a classicism and a beauty to it, so why change it?" she has reasoned.

The many examples of the New Classicists' influence at the 2013 fall/winter shows – from Raf Simons's streamlined collection for Christian Dior to the sporty couture by Montreal-born, London-based Thomas Tait – were presaged earlier in the year by a story Suzy Menkes wrote for T magazine called The Circus of Fashion. In it, she lamented the onslaught of "peacocks" at the ready-to-wear presentations. Menkes was referring to the flashily dressed fashion bloggers and independent stylists who have become street-style "stars" on websites such as Facehunter.org and Thesartorialist.com. "There is a genuine difference," she sniffed, "between the stylish and the show-offs."

Two of the fashion pros whose relaxed glamour Menkes held up as the "opposite of 'look at me' peacock fashion" are Vogue Paris editor-in-chief Emmanuelle Alt and the influential fashion editor of French Vanity Fair, Virginie Mouzat. In photographs that accompanied Menkes's story, Alt is shown wearing expensive skinny jeans and a grey-flannel Balenciaga blazer, while Mouzat poses in slim trousers and a collarless leopard-print coat that brings to mind the sultry classics Yves Saint Laurent created for Séverine Serizy, the bored housewife played by Catherine Deneuve in Belle de Jour. "Leave it to the French," Menkes concluded, "to master understated chic."

Should we be surprised? After all, it was Coco Chanel who first popularized the concept of relaxed glamour. As Alice B. Toklas, who did time as a fashion journalist, once recalled, women would flock to the boutique opened by Chanel on Rue Cambon in 1914 to buy luxuriant casuals – such as "pullovers, skirts and simple dresses" – that suited their increasingly active lifestyle (and bring to mind Philo's work for Céline). The grandes dames who lived nearby were scandalized by the knee-length hemlines and functional attire Chanel popularized. But as the haughty young Coco reasoned, "You cannot drive an automobile in a crinoline."

The beauty of Chanel's original designs, which remain the backbone of the label, is how their unobtrusive style has always framed, rather than upstaged, the woman wearing them. "Fashion is architecture," proclaimed the designer, who rightly believed that trend-driven clothing is often overpowering and makes for a poor investment.

Today, Carine Roitfeld is another leader of the Classicist pack. She perpetuated Chanel's philosophy during her tenure as French Vogue's editor from 2001 to 2010 and continues to set that tone. Not long ago, I spent the day with Roitfeld on a shoot promoting her new venture, CR Lookbook, a biannual fashion magazine she edits. Her task, as the day progressed, was to select the clothing she would be photographed in for the magazine's next edition. Although Roitfeld admired the exotic print emblazoning my Erdem trouser-and-top ensemble, she admitted, "I never wear flowers." My take? A New Classicist is confident about her style and rarely deviates from what she knows will work, seamlessly and well.

As Roitfeld and I hung out together in a makeshift fitting room, she proceeded to select her shoot wardrobe and, aside from a white satin Miu Miu bra top, everything she chose was black. She summed it up as any New Classicist would: "It's simple," she said approvingly.

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