Worn by

Simon Crompton

In conversation with Déborah Neuberg

Photographed by Eoghan Gilmore

How long have you been a father?

Simon: Eighteen years. My wife and I met at university, married at twenty-six, and had our first child not long after. Our two older daughters are now 18 and 15, and our youngest is 6. It's created a curious dynamic. With the first two, we were the youngest parents at the school gate. With the youngest, we're among the oldest. Everyone is still at home, and we all love talking about the six-year-old. Frankie, our youngest, serves as the gravitational centre of the family right now, and it brings everyone together. The harder part will come when the older two leave and she's on her own. And by the time Frankie's 15 or 16, we'll have been raising children for roughly 25 years, which may test our stamina. But there's always a positive and a negative.

Has your perception of fatherhood changed as you went from one child to three?

Simon: Not fundamentally. What does change, as children grow older, is that you start thinking about becoming a grandfather. Grandparenthood seems like the best of both worlds: you enjoy the children without needing the stamina. It feels more like a continuous flow than a series of discrete cohorts.

Was fatherhood how you imagined it?

Simon: More or less, though I didn't arrive at it with a set of expectations. My wife and I were young and naïve enough that it wasn't really going to be a problem. We simply started, and found our way through with support, thoughtfulness, and love. The deeper truth is that we all repeat the patterns of our parents. That's our frame of reference. We naturally try to recreate, or at least echo, what we grew up with. My family now resembles the family I grew up in, in many ways. That's largely unconscious, a gravitational pull back toward what felt safe and good. You have one childhood, you assume it's universal, and that assumption holds until you become a parent yourself and start comparing notes.

Déborah: You realise how specific that world was, and it was your whole world. But it's beautiful that you recognised it as good fortune to spend more time with your children. You didn't idealise being away.

Simon: With the older ones preparing to leave, I've entered a more reflective phase. There's a dynamic people don't discuss enough: the so-called midlife crisis, which affects men and women alike, often triggered when children grow older. And maybe it's a consumerism angle on it, but we assume that we could have chosen anything, that there was a consumer choice as to what we did with our life. And you naturally think of the other routes you could have taken, like you could have gotten married later or been with somebody else. But what I've come to value is the balance between stability and novelty. It's very easy to underestimate the happiness that comes from stability, love, and being appreciated by the people around you.

Déborah: Often, the people who have the most violent midlife crises are those who never questioned themselves early on, or who were pushed into life choices, including marriage and children, without having actively chosen them. When they emerge from the phase of raising small children and look back, the reckoning is fierce, almost adolescent in its intensity.

Simon: Adolescence is the first time you feel you can make a decision about your own life, because you've had no real agency up to that point. A midlife crisis must be far worse when you feel you've never had that agency, because things were thrust upon you. To look back in middle age and feel that you chose your life deliberately. That's a real luxury. And one worth appreciating.

Do you see a difference between fatherhood in your generation and your parents'?

Simon: Many differences. Our arrangement resembles my parents' generation, though with an important difference: for us, it's a choice. For my grandparents' generation, it was sometimes not a choice, it was just how things were. My grandmother went to secretarial college as a way to work in an office and meet a husband, not to build a career. Our daughters, by contrast, will be expected to have careers of their own. The shift across four or five generations, from no expectations on women to being exactly the same expectations. You can observe this dynamic at the school gates. When we first took our eldest to primary school, about fifteen years ago, almost no fathers did the morning drop-off. I was one of the few. Today it's roughly fifty-fifty, perhaps even majority fathers on some mornings. That's a dramatic shift in less than half a generation. My father grew up modestly in Manchester, attended a grammar school and became the first in his family to go to university. He later earned a business degree at Harvard and built a career as an international businessman. But when you arrive at that point as a parent, you don't impose that on your children. They grow up with the feeling that they could do anything.

Déborah: Creating an education that doesn't produce entitlement is extraordinarily difficult. Especially when the founding generation worked hard precisely so that their children wouldn't have to.

Simon: The Italians have a saying: the first generation creates, the second sustains, and the third destroys. The business is doing well, better financially than I ever anticipated, and I've started thinking about what to provide for our children. But the slope is visible: the more you provide, the less pressure they face. At some point, generosity starts to erode incentive. The difficulty is that you don't know where that point is, and it's probably different for each child.

Does raising girls affect the way you see the values of the menswear world?

Simon: The way some men in menswear have historically treated women has been appalling, and many of those stereotypes persist. There's an archetype that refuses to die: the tight-fitting suit, the exposed chest hair, the cigar, the submissive woman draped over the bonnet of a sports car. It ties masculinity to ownership, wealth, power, and dominance, and it's astonishingly resilient. The people producing these images often don't recognise the problem. To them, it's simply the visual language of the industry. My work emphasises craft, longevity, sustainability, the values around how you treat clothes. Both older girls can crochet, sew, darn, and repair things, all far better than I can. But a platform like Permanent Style carries some influence. If you use it to challenge those stereotypes, you can make people more aware, and perhaps less comfortable producing that material.

Last question, and one that's often asked of women: how do you balance your role as a father and as an entrepreneur?

Simon: The fact that this question is routinely asked of women and not of men is itself part of the problem. With a traditional division of labour, the answer is simple: work occupies nine to five, and the rest belongs to family. The tension arises when you're trying to do both simultaneously. In my case, the challenge is less about balance than about boundaries. The nature of running a site like Permanent Style is that the hours are manageable while the work is constant. Reader comments arrive more heavily on weekends. Until last year, when Manish joined us, I had never taken a single day fully off, not a weekend, not a holiday. As the team grows, I'd like to reach the point where I can take four weeks a year, a more conventional arrangement.

Déborah: Even within a traditional division of labour, asking the question creates awareness about how all of us, as entrepreneurs and working people, manage our time, our schedules, and the quality of the hours we spend with our families. Questioning fatherhood and responsibility as business owners opens up these larger questions about the businesses and the societies we want to build.

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