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There's a woman in Russia who is convinced that the eminent British fashion designer Sir Paul Smith is following her. Someone else has, over the years, been sending him random items – a surfboard, a ski, a chair, an apple – with the address and postage affixed to the object itself. Stranger yet, Smith's office receives up to 20 rabbits every week; they are shipped to him by well-wishers whose lives he has touched in some meaningful way. These curious facts and many more like them point to the playfully eccentric undercurrent that runs through all of the lanky 67-year-old's work. It's a form of whimsy, however, with a surprisingly broad appeal; that appeal will be explored this fall in Hello, My Name is Paul Smith, an upcoming exhibition and accompanying book.

"Classic with a twist" is a phrase that Smith coined long ago to describe his abiding aesthetic and, while the saying may seem shopworn now, it nevertheless remains an accurate description of what has made Smith the most successful designer in British history.

His signature twist might take the form of a floral pattern on the inside of a shirt's collar and cuffs or a single, bold red button hole on an otherwise subdued shirt. While the twist is sometimes blatant, more often the idiosyncratic detailing isn't easily detectable. In many cases, the quirky touches are only known to the wearer himself – a brightly coloured jacket lining, say, or the print of a pin-up girl on a necktie's silky underside – meaning that what often makes Smith's work stand out is the playful wink shared intimately between designer and customer alone.

"Smith injects personality into his clothing with these touches," says Jonathan Evans, senior online editor of style and grooming at Esquire. "[Smith's clothes offer] a way of dressing up and looking good but also of showing that you're doing it because you want to, not because you have to – or, even if you have to, that you're having fun with it."

"Colour," explains Toronto retailer Nicolas Kalatzis when he's asked what sets Smith apart from other designers 43 years after opening his first store in Nottingham. "When I became aware of him in the late seventies, he was using colour in a way that was entirely different and showed guys that they needn't be afraid of it. I had never seen turquoise and brown together. To me, his clothes seemed confident." Kalatzis has been carrying Paul Smith at Nicolas, his boutique on Toronto's Cumberland Street, for more than two decades, though his first meeting with the wild-haired, soft-spoken Smith took place at a low-profile trunk show in a New York hotel room. "It was Paul and [colleague] John Morley with a couple of rolling racks and clamp lights," he says. "No one really knew who he was in North America so he was selling his clothes personally. He was an incredibly down-to-earth guy then and he's managed to stay that way."

Smith was born in Beeston, near Nottingham, in 1946. His father, Harold, sold clothing door-to-door and wangled Paul a job in a clothing warehouse when he left school at age 15. The only part of the day that Smith looked forward to was his bike ride to work, but his dreams of becoming a professional cyclist were dealt a hammer blow after a crash put him in traction. The upside of his three-month hospital stay was a friendship he formed with three boys he met there. Once recovered, these new pals asked Smith to join them at their favourite pub, which was also a haunt of art-school students whose conversations energized him and led to an interest in design and, eventually, night classes in tailoring.

The pub, in fact, turned out to be the locus of Smith's transformation in more ways than one. It was also there that he met Pauline Denyer, an art-school tutor from London who would become his girlfriend, business partner and wife. Drawing on Denyer's encouragement and design skills, Smith opened a tiny Nottingham boutique with a long name: Paul Smith Vêtements Pour L'Homme, the only boutique outside of London carrying labels such as Kenzo and Katherine Hamnett.

While the Gallic name may have seemed incongruous, even wanky, in the English Midlands of the early 1970s, it was somewhat prophetic of Smith's trajectory in the fashion world. Within six years of the boutique's opening, he showed his first men's-wear collection in Paris under the apt and unapologetically Anglo-Saxon moniker Paul Smith. Three years later, Smith opened his first London store in Covent Garden, where, in addition to his designs, he offered "finds" for men including well-designed, hard-to-find office supplies and household accessories such as calculators, Filofaxes and even vacuums – an offshoot of his propensity to amass and celebrate the kitschy, the colourful and the curious.

Perhaps ironically, it was in Japan that Smith first found international renown as a quintessentially British designer. (Smith now has more than 200 outlets there, compared with 15 in his native Britain and just five in the United States.) In 2000, the son of a "credit draper" was made a Commander of the Most Excellent Order of the British Empire by the Queen, although the title has done little to affect Smith's particular brand of exuberance.

Smith says that he has resisted the urge to grow old with his customers and believes that he has remained true enough to his youthful self to appeal to the 18-to-30 market. Another secret to his enduring relevance has been to not take himself too seriously – a sentiment that he invites customers to share with every droll detail he tucks into his designs.