How to act your age, not your shoe size – but with shoes.

We have noticed more than a few of you asking questions on our social media channels about dressing appropriately for your age. So, whether you are a younger man, or an older chap, we thought we would try to give a comprehensive answer to satisfy all of you, in one fell swoop. Step forward Mr Chris Wallace, our US Editor, who knows a thing or two about avoiding the pitfalls.

**How do I dress stylishly, but still appropriate for my age?

From various, via Instagram **

I apologise in advance; this one got a little existential. But, how could it not. In response to several queries about age-appropriate dressing, my first inclination was to talk about dressing for one’s age, like, the time we are living in. In this digitally nomadic, tech-inflected hygge, streetwear moment (SoulCycle at 9.00am, WeWork at 11.00am, The Butcher’s Daughter for a grain-bowl lunch; rinse, repeat). But you don’t come here for rote answers (you will not hear us utter any malarkey about age being just a number). This is hard-hitting advice we’re serving, and advice, like style, is not one-size-fits-all.

Take me: I am a 43-year-old creative professional, working in an open-plan office environment and living in a metropolis. Button-down shirts and blazers, right? Well, you’d think so (and so did I for much of my thirties, when I did dress in what Mr Andy Warhol might call the editor’s uniform), but these days, I’m a T-shirt-and-jeans type of guy (I am from California, after all). Just about every day I wear a Massimo Alba henley, a Rick Owens Stooges leather jacket, black jeans and a pair of boots by Red Wing Shoes – a uniform at once too specific (vaguely reading “biker”, although I have never once been on a motorcycle), and too youthful for my years (I am not, have never been and will not ever be cool, even if my Rick Owens jacket wants to suggest that I think as much).

Could I continue to wear this uniform into, say, my seventies? Well, functionally, yes – I’m a big fan of buy-it-once-buy-it-for-life sort of sustainability. But I actually have been starting to understand what Mr Owens himself has said, that he feels too old for leather, that it feels too heavy on him now. Maybe I just need some bone-density vitamins. Or maybe it is time to pivot to satin or something. In fact, I recently picked up a silky Dries Van Noten Western shirt (which I imagine wearing under a leather jacket, with aforementioned boots). It’s a bit out of my wheelhouse, but an evolution. And let’s remember that while style can be self-expressive, a declaration of personality, values and brand affiliations, it is also a wonderful realm in which to experiment, a way to find oneself. And why should that be any less true in one’s forties, fifties or sixties than it is in adolescence?

Of course, many of us work in worlds where to veer too far outside the established norms of attire would be to court the wrong sort of attention. Your law firm isn’t quite ready for those Rhude Hawaiian shirts just yet. But I bet you could sport some Common Projects sneakers with a nicely tailored suit and a polo shirt? And, once you are there, it is not a long jump to a suede blouson, say, over a luxurious rollneck with office-appropriate trousers and desert boots? OK, maybe that’s too far. My point is that you can inch your way toward a new you, one garment at a time.

Do you like the detailing on that Takahiromiyashita TheSoloist blazer? Maybe try it and see if the utilitarian vibe is for you. Liking the checks on that Gucci houndstooth coat? Maybe follow that into new patterns. And, who knows, if Balenciaga’s Triple S sneakers really speak to you and you are a 65-year-old professional, you may be seen as the eccentric peacock at the office, but by nurturing that interest into garments that suit the “you” you want to see in the mirror, you could become the next “advanced” street-style legend!

Treat our Essentials list as a safe house if need be, a place to which you can return if you are getting lost in the wilderness, but then venture out again, chasing the sirens as they call to you. Do you, one piece at a time. You’re old enough to do what you want, and young enough to give it a shot, I guarantee it. And there are no other requirements for this journey. Punch the ticket, take the ride.

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