I have interviewed 84 people up to this point for Five Fits With, but never anyone with a career as storied and long as Sir Paul Smith CH CBE RDI. His eponymous brand is 54 years old, with absolutely no signs of slowing down. He’s won countless awards and accolades, written books, collaborated with many of the world’s biggest artists and brands, all of which you can read upon a quick search of his name. Surely I need not explain why he is one of fashion’s biggest living legends. So, what would you ask the man who has lived as an exceptional a life as his?

Well, as it turns out, whatever you like. It wasn’t a surprise—his reputation precedes him—but Sir Paul was kind, open, and best of all, extremely fun. He was literally skipping up the block, bringing me along for the ride. “I’ve done a couple of photo shoots,” he said with a sense of good, dry British humor. After the shoot, we sat down at his Wooster Street shop during his brief visit to New York to check in on his namesake brand’s takeover of the Nordstrom Clubhouse and generally get a lay of the land Stateside. The conversation covered everything from his brand’s foundations and growth to creating custom trousers for Jimmy Page, being knighted and married on the same day, why men’s clothing never really changes, and plenty more.

Clothing, shoes, and accessories (throughout) by Paul Smith—except for the vintage belts.

Fit One

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Tell me a bit about how you first became interested in clothing and style.

I used to be a racing cyclist. That was my dream. But when I was 18, I had a bad accident. I suppose I was interested in clothes a little bit, but not a lot. After the accident, I started to hang out with all the kids from the local art school. There were fashion designers, architects, photographers, and that's when I started to think, "Oh, I wonder if you could do this for a living and it's quite nice to make the effort with clothes." The rest, as they say, is history, I suppose.

Do you remember your first big break?

Never. There's never been a big break. There's never been a big break. It was always very gentle.

Really?

Never something like that. It was just always working in a store as a shop assistant, opening a tiny little room, which I called a shop, then making a tiny collection to sell to other people. Then just growing it and growing it and growing it. So never really anything in a big leap.

I'm a massive rock fan, and particularly a Led Zeppelin fan. I read you were dressing Jimmy Page when you were 18. How did that come about and what was that like?

I lived in the middle of England in Nottingham, but I used to go to London every weekend, and I don't know quite how, but we used to stay in a squat. My friends were in a place in Notting Hill, which now has 5-to-10-million-pound houses. Then, we were sleeping on the floor, and above and below us were bands. Brian Auger and the Trinity, and The Graham Bond Organisation, both quite important bands in Britain, but not well-known worldwide. And so, you got to hang out with musicians who were just starting out. Clapton, Page, John Mayall, The Yardbirds, a very young Rod Stewart when he was 18 and cool. I measured Jimmy for a pair of trousers. He had a 24-inch waist. The bottoms of the trouser were a 28-inch [leg opening]. He was so tiny. They were crushed velvet trousers that we made. Then I got to know a lot [of popular artists]. I just designed a cover for a Rolling Stones album, which was a limited edition. We're working with the Stones on clothes for the tour. We still work with a lot of bands all the time.

Fit Two

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Shifting gears a touch, you were knighted and married on the same day?

Yep. It was a busy day.

What happened there? Minus the obvious.

It was completely by chance. I'd been living with my girlfriend for years and years and years, and then she said she wanted to get married, so I said, "Sure." She chose a date, months in advance. Then I got a letter from the Queen at one point saying she wanted to put the sword on, and my assistant at the time said, "We really ought to find out what the date is because you travel so much." She spoke to Buckingham Palace, and then she put the phone down and she said, "You're never going to believe it." And I said, "What?" And she said, "The investiture is at 11:00 and your wedding is at 4:00." So I said, "It looks like it's going to be a busy day." So, we had that in the morning, a lunch, then the wedding, and then a party at Tate Modern, which is the only time they've ever allowed a party at Tate Modern. That was quite special.

How do you continue to find inspiration for building new collections?

Oh, that's easy. The inspiration is easy. Running a business in this crazy world we're living in is very tough because of the war and moods and all sorts of things. In the UK, it's Brexit. The inspiration is all around us, so I've never had a problem with inspiration. My father was an amateur photographer, and so at the age of 11, I was given a camera. By looking through that little viewfinder of a camera, as you know, you just learn to look and see. You don't just look, you actually see, and you work out the shot. That helped me with observation. I've taken photographs over the years. I worked for The Face magazine, Arena, Architectural Digest, I did a cover of Vogue, lots of Japanese magazines.

Fit Three

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No doubt you understand what it takes to keep the longevity of a brand intact. What have you learned about style and the transience of trends?

First of all, that in clothes for men, it never really changes so radically. I call it a nudge rather than a shot, because men are creatures of habit and they wear more or less the same clothes, apart from when you get the crazy catwalk shows in Paris, which are attention-seeking clothes, which generally speaking, nobody really wears a lot of those clothes. You learn not to rock the boat too much, just to design. You need to keep up with the trends because corduroy [Smith points at my shirt], for instance, is popular again right now, whereas for a while it wasn't. Color is a little bit more popular for some guys now.

Has your personal style changed much from the inception of your brand to where you sit today?

Not really changed. It's always been... It's a very overused phrase, but it's classic with a twist. So what it means is that, generally speaking, the clothes are very wearable, but they've normally got a little secret or a little unusual point, or then there's nothing unusual about the clothes, but it's the way you put them together. It's always been just slightly contradictory or to do with kitsch and beautiful, or rough and smooth, or workwear with posh, or playing with contradictions.

I read that you dreaded that exact phrase: “classic with a twist.” What about the phrase bothers you?

Only because I've said it so many times, that's all. It doesn't bother me at all. It actually describes it perfectly.

Fit Four

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Can you walk me through an average day in your life?

There is no average day, unfortunately. It's very diverse. The only thing that happens every day if I'm in UK is I swim at five every morning. That's the only thing that's like a habit. But after that, it can be with students or with my design team or designing shops. I was in Paris for a day last week, and then I was in Munich the week before, and here now.

So, always all over the place.

Which is very nice. It's really nice.

Is there a question you've never been asked in interviews that you would like to be asked?

Okay, well, that's a good question. I've been interviewed a very large number of times, as you probably know.

It was difficult to prepare for this because I had to tread some of the same ground, but also wanted to go somewhere new.

A lot of people don't know I'm quite interested in classical art as well as contemporary art. It's highly unlikely that [interviewers like you] would ask about Caravaggio or Titian paintings because you just wouldn't. They're not relevant to Esquire. But I do know quite a lot about Titian and Caravaggio.

Do you have a favorite museum in the world?

Not really. I don't like the word “favorite.” I find it's a problem, favorite, because it very much depends on your mood. Certainly, the National Gallery in London is wonderful, which is very classical. But then so is the Tate. It depends on your mood.

Fit Five

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Is there an exhibition you've seen most recently that you were taken with?

Nicholas de Stael in the Museum of Modern Art in Paris. Wonderful work. He was so stylish. He passed away in the 1950s, but there's a picture of him in 1955 that looked like today. Pleated trousers, dark shirt, cool sandals. Slim guy, he looked very good.

If you had to wear one outfit for the rest of your life, what would it consist of?

I tend to wear suits every day because I find them really useful. I've always got pens, I've always got a notepad, always got my spectacles, always got my keys, always got my credit card. Generally, with a navy blue suit, you can't really go wrong. You won’t believe this, but during the pandemic, I wore a suit every day, even though I was in my building—which normally has 180 people in it—on my own for the whole 16 weeks with nobody else there. I wore a suit every day, which proves it's just a habit. I never think of it as a suit. Whereas a lot of people find a hoodie or a piece of knitwear more comfortable, I never really think about it.

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