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Stephen Jones is known for his outrageous and opulent hat designs.Courtesy of Stephen Jones Millinery

One of the most important milliners of our time, London-based Stephen Jones has dressed some famous heads from Grace Jones to the late Princess Diana, and worked with designers from Jean Paul Gaultier and Commes des Garçons to Marc Jacobs and John Galliano for Dior.

Jones' fantastical style and gentle demeanour are legendary, and his sensitivity to the art of personal expression has won him a huge, multi-generational fan base. The 58-year-old studied fashion at London's Central St. Martins university and created his first line of hats for Fiorucci in 1979.

He's also a featured presenter at Montreal's upcoming Fashion & Design Festival. I spoke with him recently about how fashion has changed and the biggest challenge facing young designers.

How have you been riding what's gone on these past 10 years in fashion? There's so much that's dramatically different.

The whole world is different and fashion that has any relevance has to mirror that. Ten years ago it was a different generation: Nicolas Ghesquière at Balenciaga, Marc Jacobs at Vuitton, John Galliano at Dior, Alexander McQueen. Fashion was definitely with a capital F. It's much quieter now. It's certainly – as we say in fashion – less fierce than it was. It's more discrete, more wearable in a way and more relevant to people's lives. But although people do wear more jeans and T-shirts, they still love to look at the crazy ball gown.

It obviously speaks volumes about what's happened to artistry in fashion and how commercialism has really dealt a big blow to the creative factor. How does someone like you come to terms with that? How do you embrace that?

Well for me, it's the other way around. What people want from me is something which is creative and unusual, because my hats are handmade in England and it's always going to be an expensive hat. So if someone's paying a lot of money, there's no point offering them a basic object, and they are not even interested in that.

It's great to hear that you still feel there is an appetite for that level of style.

Even more so in the world where things have such a homogenous sense. It means that something which is individual and something which is handmade suddenly seems almost more important.

I'm wondering how young designers are going to work within that sensibility. You're saying their creativity should be encouraged to the max, but what happens when they're actually trying to pay the rent?

Well, I was talking about just myself. I think if you're a young designer now, boy, things are really tough! I did some teaching a few weeks ago and I asked, "So what's the biggest influence on your design?" I was thinking they might say Chanel, or music, or social media, but they said, "Having a £50,000 overdraft when you leave college!" That's what shapes their design, naturally, they're thinking of how to be commercial and sell.

The focus of what is taught now is different than when I was at college. We were taught that commercialism would come through creativity. What is taught now is that you have to be a professional and you have to create a business – which is correct. There's no easy solution. The one thing that I do know is that in 20 years time, people will still be buying fashion, because people are always fascinated with how they present themselves.

How did you feel about Dana Thomas' book Gods and Kings, on the height of Galliano and McQueen? She lamented that a "golden age" of turn-of-the-millenium fashion was quite over in her mind.

Fashion has relevance when it changes and twists and turns and becomes a mirror for our society. The reason that the New Look from Dior was so important in 1947 is that it mirrored the times. The reason that Punk was so important in 1976 is that it mirrored the times.

What we're waiting for is a new generation of designers who…actually correspond with the world that we live in. Those will be the people who are important. When we look back at the glory days of Galliano and McQueen, they were right for the times. But if they were doing the same thing now, I'm not sure it would appear as strong, because we've moved on.

It sounds like there's not too much you miss about the good old days and not being able to recapture that.

Well, perhaps my youth. I wouldn't change a thing. I was very lucky to be starting at the beginning of the '80s. Fashion was this huge new unchartered territory, so we were very, very lucky to have been a part of that. That's when people were really hungry for fashion. Now, there's almost too much.

This interview has been condensed and edited.