For Mr David Fischer, it began, as it so often does, with his father. There had been Swatches and G-Shocks, of course, but his first serious taste of the world of high-end watchmaking came in his late teens. “My dad bought himself a Da Vinci from IWC,” he says. “He explained the calendar functions of the watch, showing you everything from the moon phase to the day, date, month, year. I loved the little details – I always have, even when I was a kid – the way it even comes with a little tube in the box where you’ve got the spare pieces for when the years run out, so the watch continues running way past your lifetime. That started my watch education, you could say.”

Quite a start. The IWC SCHAFFHAUSEN Da Vinci is famed among watch collectors for its groundbreaking perpetual calendar movement, celebrated for introducing a simpler, more user-friendly take on a notoriously complex function. Designed in the 1980s, at a time when the future of mechanical watches looked bleak, it was a huge investment in innovation that went completely against the grain – but it cemented IWC’s intentions to revitalise traditional watchmaking and drew praise from across the industry.

It was another IWC legend, however, that would capture Mr Fischer’s own imagination and become, as he puts it “my dream watch back then”, the Big Pilot’s Watch. No less of a departure with convention than the Da Vinci was 25 years previously, however, it hails from the other end of the horological spectrum in almost every way imaginable. It was – as you cannot fail to grasp from the name – enormous for the time, at 46mm across, and almost wilfully simplistic in its design, faithful as it was to pilot’s watch designs from WWII.

Bolstered by an upbringing that saw the family move around Europe – Barcelona, Brussels, Frankfurt – before alighting in Geneva in the late 1990s (“There you get a whole different level of appreciation for the craft, for the brands; everybody’s so insanely well informed,” he says) Mr Fischer’s interest in watches was influenced by a trait that has defined pretty much every decision he has made: a desire to stand apart from the mainstream.

“The Big Pilot was my dream watch for some time,” he says. “It was so cool. So big and sporty, but still elegant, with this chunky leather strap, the big crown and the two big rivets on the strap. I was always a person who wanted what others didn’t have. I thought it was too easy to buy what everyone else is buying; at that time, it was interesting for me because it was ‘not Rolex’. Plus, of course, it had the connection to their heritage. Being in my early twenties, it was kind of out of reach for me as a watch back then. That said, I could have pulled it off because I’m a pretty big guy, at 6ft 4in.”

That desire to run away from the crowd has served Mr Fischer well. Having studied business administration, he found traditional career paths at odds with his interest in fashion and started Highsnobiety as a blog in 2005, long before most people had noticed the growing interest in men’s style and streetwear in particular. Over the past 15 years, he has turned his passion for sneakers and alternative culture into a design, culture and style empire that covers everything from top-end Lego sets to Ms Alexandria Ocasio-Cortez (and yes, still lots of sneakers).

“No matter what, I am totally 120 per cent into ‘if you know you know’, with anything,” he says. “If I’m buying a pair of Red Wing boots, then I’m not going to buy the standard, off-the-rail pair that 99 per cent of other dudes are walking around in. I’ll buy the black special edition that they made for Japan, and you don’t see the difference anywhere on the shoe, but if you know, you know. Even when I was a kid, I remember being into that. These little details, the little hints. That’s what makes me tick.”

What that translates to, in the watch world, is a growing appreciation of the subtle touches that distinguish, say, a stainless-steel case from a platinum one. And then, of course, there are the literal hidden depths to any mechanical watch: the movement within. Confronted with IWC’s latest Perpetual Calendar – whose in-house movement is descended directly from the one that powered his father’s Da Vinci all those years ago, Mr Fischer’s reaction is immediate.

“I loved it,” he says. “I thought it was awesome. I’m very design-conscious when it comes to watches, but I can appreciate the insane detail in the work and the beauty of the mechanics.

“In fact, I’m very lucky, I do own a Portugieser already – I got given a rose-gold Portugieser 7 Day from my parents-in-law for my wedding, and that is just a gorgeous watch. I hardly ever get to wear it, because it’s a little ballsy, especially in Berlin, so it’s something that comes out for certain occasions. But still, I love that about it as well, it just feels special to go to the bank, get it out of the safe. It’s a special feeling that you get when you’re wearing it. This one here, I love that it is relatively everyday – the blue dial, black strap, steel case, it doesn’t shout. I like that it’s a whole lot less obvious to people than, say, a Patek Philippe.”

Given the choice today, between the watch that was once his dream purchase and the Perpetual Calendar, he cannot decide. But he concedes that the Big Pilot’s aesthetic remains a great match for his everyday style. Surprising, perhaps, that the more traditional, more complicated and classically styled timepiece is running head to head with the Pilot, but if we’ve learnt one thing about Mr David Fischer, it’s that he never makes the predictable choice.