Simon’s Eternal Style

Thanks to, Simon Crompton has become one of the world’s most prominent figures of authority in menswear. Plaza Uomo travelled to London to catch up with the journalist-come-author and have a cheeky nose around his wardrobe. 

The origin of the suit that started a new and exciting chapter in the life of Simon Crompton, one of the world’s greatest influencers of the menswear scene, is perhaps not what one would expect. 

“I remember buying a suit in Zara,” Simon explains. “It was a grey pinstripe with two buttons at the front. I’m sure it was ghastly but I was very excited about it. As time went on I realised it wasn’t made very well and I tried to understand the reason for the poor quality. Having to learn all the basics awoke the nerd in me.” 

This was during the mid-noughties and Simon had just started his career as a journalist at a lawyers’ trade magazine. Looking smart became part of the role as he spent time in environments with invisible dress codes. But the more he learnt about suits and the making of them, the more he came to understand that his peers did not share his interest in clothes.

“A friend of mine ran a women’s fashion blog and she told me I should start my own blog. It had never crossed my mind before, but then when she suggested it…” 

This was the starting point of, the website – Simon wants to avoid calling it a blog – that went on to become one of the most renowned forums on tailored menswear. Since its launch in 2007, Permanent Style has been ranked in the top ten men’s fashion blogs by New York Times, and the British newspaper The Times named it one of the world’s 15 leading websites for men’s fashion. With 300,000 readers every week, the website has turned Simon into a figure of authority and he is frequently hired by magazines such as Financial Times, GQ and Robb Report. His first book, Le Snob Guide to Tailoring, was published in 2011 and the sequel, The Finest Menswear in the World, released four years later.

“There are three different ways to define what I’m doing,” Simon says. “The first is style. People talk about classic style, but what they really mean is formal style, like suits, jackets, ties and so on. Second is the element of craftsmanship. We focus on things that are handmade. Better quality items tend to be made by hand. Third and last, there is a sense of luxury. Most of the stuff I’m writing about now revolves around luxury, but the artisan side of the luxury industry.” 

So when you talk about luxury, you are referring to the craftsmanship behind it rather than the label? 

“Precisely. Luxury is a strange term. Today its meaning is expensive fashion, more or less. I would say I write about artisan luxury, which is built on knowledge and craftsmanship.” 

We are in the garden of Simon’s new house in East Dulwich. It’s a quaint area in South London which, in the last 20 years, has gone from a rough ghetto to a gentrified family-oriented neighbourhood serving London’s careerists. 

Simon’s wife and children are away at his parents-in-law for the weekend. This gives us plenty of time for the interview and, perhaps more importantly, to have a look through his remarkable wardrobe. During his blogging career, which spans almost a decade, he has visited more than fifty of the world’s most high-profile tailors. From Cifonelli in Paris and Anderson and Sheppard in London, to Liverano & Liverano in Florence and B&Tailor in Seoul. When asked how many suits and jackets have been made for him, Simon chuckles. “Way too many!” He continues; “definitely more than 50. We recently did a post on how many tailors I’ve visited. Thirty-nine! Madness.” 

But it is precisely this experience and know-how that has made him an expert. 

Born in London in 1981, Simon Crompton’s first fashion memory is of his grandfather. “He really knew how to dress,” Simon says. “He wasn’t into it the way I am, but he cared deeply about his appearance. He worked in a bank and sported three-piece suits and a bowler hat long after it had gone out of fashion as the industry’s default outfit.”

Many of our generation reference their grandparents when talking about style inspiration. It is as if our parents belong to a lost generation in terms of style. 

“Yeah, that’s right. No-one taught me how to dress. I did. I’ve always felt a bit bad about not being able to share an interesting story about that.” 

As a teenager, Simon dreamt of becoming a novelist. Once he had completed school, he applied to Oxford University and got accepted on the PPE program, Philosophy, Politics and Economics. “Towards the end, I planned to have a go at journalism. I joined a training program at Euromoney, a publishing house specialising in titles aimed at lawyers, solicitors, bankers and accountants. That’s how I learned about journalism and subsequently got my first job. It had never been my intention to work at a trade magazine, but I actually really enjoyed it. As a junior member of the team, I had to be very analytical and fully grasp the legal structures when interviewing senior lawyers. You have to be confident and know the topic inside out.” 

You still work there today? 

“Yes, same place, but a different role.” 

So Permanent Style is something you do in your spare time? 

“Yes. I can publish comments and minor things during the day, but it’s mostly something I fill my evenings and week- ends with. It never feels like work. I im- agine it’s the same for those that are really into football. For them, there’s probably nothing better than sitting down to study and discuss different matches and results.”

Do you know who your readers are? 

“I do meet some of them at the trunk shows here in London. Many Italian tailors come here and they tend to run behind schedule, so there’s often a group of guys outside waiting. Most of them know who I am and it’s great to sit down and have a chat with them. I learn about their likes and dislikes, purchases and budgets.”

Is there anything in particular that they have taught you? 

“I’ve learnt that there are two types of guys. The enthusiast who spends endless amounts of time and money on this type of clothing, and then there’s the friend of the enthusiast, who’s happy to tag along.” 

That’s an interesting observation since the thirst for knowledge about tailoring has grown in recent years. Is this something you have noticed as part of your work on the website? 

“Definitely. The site has been up for ten years and I have been riding the wave of a growing interest in craftsmanship and menswear. I think nerdiness runs in the blood of men. That’s why they like cars, sports or Star Wars. They’ll find an interest that they can get bogged down in with a group of mates. And now men are becoming interested in clothes and the craftsmanship of clothes making. Of course it helps that it’s now socially accepted to care about what you wear.” 

How do you know what to write about? I expect you wouldn’t cover someone who doesn’t live up to your standards on the website. 

“No, I wouldn’t. The reason I rarely write a negative review is because I pick those that I know are good. But I feel a responsibility to try things that are new or different, that my readers are likely to buy. For a while I ran a series called something like ‘five brands that don’t measure up’. One day, someone commented, ‘Ok, so nothing to see here in other words.’ It made a valid point.”

Do you contact the brands or do they approach you? Is it harder today now that you’ve seen so many? 

“There’s no shortage of things to write about. Most of the time, I tend to write about something that has been recommended to me, either by friends or readers. Sometimes I respond to an idea sent to me, but that is generally not the best method. Ideally, it’s something I’ve found myself.” 

Your relationship towards writing is fascinatingly hands-on. You sometimes go into great detail about how certain patterns work with certain fabrics, or how to pull off a particular colour sweater. Is it a conscious strategy? 

“It happens naturally. People often say my writings are analytical and fairly in depth. I think it has to do with my journalistic background. I’ve always been keen on doing the research, ask the next question and explain things. The tendency of fashion journalism to be shallow is problematic. There’s no depth or analysis. People write about liking a particular style or garment, but the context is missing. My verdicts are meant to be informative, like ‘This one is good because of its length’, or ‘The trousers are cut in a way to make you look taller’. Going deeper helps readers understand and learn more.” 

Absolutely, but to me, you’re exceptionally detailed. Sometimes you describe the feel of a garment against your skin. 

“Yes, I think this is the type of advice guys are looking for. It’s a strange time right now. People rarely wear suits, but it’s more important than ever to dress smart and be seen as professional. It’s a difficult balance. It’s hard to look elegant when wearing a jacket and trousers. Women often say it’s easier for us since there is a template in place for how we’re supposed to look. But in fact it’s quite complex. It becomes easier with the right kind of information at hand.” 

Why do you think it has become more socially acceptable for men to care about their clothes? 

“I think there are a number of reasons. There’s the social aspect, that it is simply more acceptably for men to spend money on their clothes, hair and appearance. It is hard to pinpoint exactly why, but it relates to a number of things and is tied to modernity. Then there’s the fashion angle, in that the fashion industry has realised that menswear is a growing segment and has begun to push it. Just look at the acquisition of Loro Piana and Brioni. The big companies have become aware of the financial opportunities available. 

The crisis of 2008 also plays a role. As a result, people began to reminisce, and this has spurred the vintage trend and boosted the popularity of traditional phenomena, such as Tweed Run. It’s also fuelled the movements around craftsmanship and quality. The combination of all these have resulted in the ever- growing popularity of Savile Row, since it unites classic menswear with values of craftsmanship and tradition. 

“And finally, social media has played a massive role in accelerating these trends. It used to be difficult to find information about men’s fashion, but today there’s an abundance of sources.”

Considering your experience of tailoring, how often do the tailors
ask you for advice? 

“It happens, but not all the time. I’m happy to give advice and my best relations are with those that are responsive.”

What type of advice do you normally give? 

“Because of its appropriate design for modern office environments, the soft-tailoring trend, which originates in Naples, has become very popular lately. Many British tailors want to adopt it, but don’t fully understand how to go about it. The problem occurs when they change something by twenty percent, when they should in fact change it by ninety percent. You can’t simply make the shoulder softer without taking into account how it will affect the lower part of the jacket.” 

Have you ever considered starting your own brand? 

“It’s crossed my mind. I currently do a number of collaborations, which is very satisfying. It gives me the chance to develop products that I can’t find else- where. But I don’t think I can do both. I can’t be a commentator and have my own brand. I could possibly become an advisor or consultant.”

The last question: How long do you think you can keep doing this before your wardrobe explodes? 

“I don’t think the wardrobe is the limit. I’m pretty good at handing things down when I get new stuff. My brother and brother-in-law are very grateful to be given clothes.”

Lucky them! 

“I know! So that’s not what it is about. The end would be if my interest in clothes died off. The toughest thing would be if there was a fundamental shift in fashion and people stopped wearing bespoke.”

Is that likely to happen? 

“No, I doubt that. I am of the optimistic view that social media creates permanent niche groups that will survive on their own.”

“My Cartier Chronoflex. Gold on a custom-made alligator leather strap from Jean Rousseau, London.”


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