Men – many of them, at least – don’t really care about their clothes, according to Simon Crompton. “They just want to not look stupid,” he says. “Not to be wearing a completely different thing from what their friends are wearing. Not look an idiot, that’s the main concern.”

It may sound strange now, but before founding Permanent Style – the site and now magazine that, over the past two decades, has become a leading authority on menswear – Crompton himself wasn’t overly bothered by what he wore, either. “Which is always disappointing, because you expect that there’s this great origin story,” he says. “I wasn’t into this world at all. It was only when I started working in the City, around people who wore suits and ties all the time, that that interest was born.”

In his day job, Crompton largely wrote about finance, becoming the head of product strategy at Euromoney PLC. But rather than just fit in, he wanted to understand the banking sector’s dress code. He puts that down to his training as a journalist. “I was investigating it,” he says. “My instinct was to go deeper, to try and find out more and more about it.

“When you’re into something, you talk about it way too much,” Crompton says. Pretty soon, he became something most men fear as much as being badly dressed: “one of those boring people in the pub”.

“A friend of mine, who wrote a very successful dating blog, said, ‘Guys do have an interest and do want to hear about this. Just not at length in the pub. But if you wrote a blog about it…’”

This was 2007, the early days of the #menswear era. That Mad Men first appeared that same year probably helped a blog about suiting get off the ground. But to still be here almost 20 years on shows gumption.

“It was very much amateurs who were was exploring it for the first time, but didn’t necessarily have the professionalism to keep it going consistently,” Crompton says of the wider field. “When you’re writing on a platform like that, you naturally start off quite narrow. You want a distinctive voice – you’re interested in one particular thing and once you write one article on that, then another thing comes off it, and another thing…”

Crompton jokes that he might have “completed” that branch of menswear. “Last week, I went to see a button factory in Connecticut,” he says. “It was great, so much better than I thought it was going to be. Who wants to go see buttons being made? But it’s fantastic. There are very few menswear crafts I haven’t now seen being made, and I hadn’t seen buttons before.”

The focus of Permanent Style has, of course, broadened over the years. Early readers sometimes questioned when Crompton began to also consider off-duty items. “Well, what do you think I wore at the weekend?” he says. “I wasn’t wearing a suit.”

Then the Covid pandemic forced us all to reconsider our wardrobes. Crompton remembers talking to Blamo!’s Jeremy Kirkland about this. “We did a series of videos, just chatting every week on Instagram,” he says. “And we just started pulling out favourite pieces of casual clothes, like an old Filson jacket I had, a pair of jeans, a bomber jacket… And you start to realise there’s so much stuff in this area as well that we can talk about.”

In fact, having almost too much to talk about is part of what has inspired Permanent Style’s leap into printed press – issue four of its magazine is out now. “If you’re writing a blog piece, you’re writing three of them a week, you can only spend a certain amount of time researching it,” Crompton says. “Whereas, if you’re doing a magazine every six months, then we can do more things – with the last issue, the whole team went to Los Angeles. Manish Puri, our deputy editor, spent two full days with the costume designer Mark Bridges, who did Phantom Thread. He had dinner with him, went to his house, went to all the vintage places where he sources the clothes. Then the next night, Mark invited Jenny Eagan, the costume designer on Knives Out. And that’s now a 10-page feature in the magazine.”

Other contributors to the magazine include Nico Lazaro, the Grailed cofounder who now writes The Bengal Stripe on Substack, and a Belgian polymath called Bent Van Looy. “He’s a pop star, he has a band called Das Pop,” Crompton says of the latter, who was also the live drummer for Soulwax. “He’s a voice actor, an illustrator. My favourite claim to fame for him is he was the Flemish voice for Paddington.” For the magazine, Van Looy spent six months investigating a secretive Belgian bootmaker – shoe leather journalism, you could call it.

Ian Leslie, the John & Paul author, who runs The Ruffian Substack, also contributes to the magazine, while Derek Guy has previously written for it, too.

“Another nice thing about the magazine is we’ve been able to work with a lot more of these people,” Crompton says. “A lot of MR PORTER readers will already know the blog, but they wouldn’t necessarily know the magazine because it’s newer. I really do think it’s the best expression of what Permanent Style is.”