How Should A Man Dress In His 40s?

I wrote something last week about why shopping for clothes seems to get harder after 40, which is something I hear all the time from new clients and, having written it, there was another question sitting there almost immediately afterwards, which I suppose is the obvious one. If you’re in your 40s, shopping has somehow become more annoying than it used to be, half the things you try on don’t seem to fit properly anymore, and the rules around what men wear have changed quite dramatically since you were 25, what the heck should you actually be wearing?

So I started thinking about how I’d answer that if you were sitting with me in person in the workroom, and I think I might annoy you slightly because I’d answer your question with another question.

“What does your week typically look like?”

Not what you do for a living, necessarily, because although it's important, it doesn’t always tell me enough. I’ve got clients who work in exactly the same profession but dress completely differently because one is in an office five days a week seeing people constantly and another might work from home a couple of days a week, come into London for meetings on Mondays and Wednesdays, and then be on a plane to somewhere on Thursday morning. So when I say, what does your week typically look like, I mean literally take me through it. Where are you going, who are you seeing, how do you travel around, what happens after work, and, while we’re at it, what does Saturday look like too, because you don’t cease to exist at 6pm on every Friday, right?

There are 1000s of influencers out there that won’t care about any of that and will happily tell you exactly what you should be wearing, depending on who’s paying them what. But I struggle a bit with the idea of telling men how to dress in their 40s, because age alone tells me almost nothing about what you need.

I could have two 45-year-old men sitting in front of me, and one is a senior lawyer who spends his week moving between clients, meetings, dinners and events while the other runs his own business, works from home when he can, travels a lot and hasn’t worn a tie since he can’t remember when he last wore a tie. If I gave both of them the same list of ten things every man over 40 should own, I’d be doing at least one of them a pretty big disservice; probably both of them to a greater or lesser degree.

And yet this is more or less how most advice about dressing in your 40s seems to work.

You reach 40 and apparently there’s a little sartorial ceremony nobody warned you about where certain things are taken away from you, other things are handed over, and somebody solemnly informs you that you’re now ready for your navy blazer and penny loafers.

I don’t really buy any of that.

I’m in my late forties as I write this, and though during the working day you’ll almost always find me in a three-piece suit and tie, outside of that I wear jeans all the time. I wear sneakers. I ride around London on a Vespa on certain days, when even for business I’ll wear smart tailored (by me, of course) jeans with a casual jacket and shirt. I’ll quite happily wear a plain white T-shirt and jeans when I’m not working, and I don’t think the arrival of my 50th birthday is going to cause me to wake up the following morning, look at my wardrobe and decide I’ve become too mature for any of those things.

What has changed is how I want those clothes to fit, how I combine them together and what I expect them to do for me, and I think there’s an important distinction there because dressing well in your 40s, as far as I’m concerned, isn’t about removing things from your wardrobe because somebody has decided you’ve aged out of them.

It’s more about becoming increasingly particular and considered about the version of those things you wear.

Jeans are a good example because I spent years wearing mine fairly close. Actually, I spent years wearing practically everything fairly close because I was in decent shape, my weight hardly moved, and I liked that precise silhouette, so why wouldn’t I? It suited me, and there was no particular reason to change it.

Then my body did change a bit.

Nothing terribly dramatic happened, I should add. I didn’t wake up one morning shaped like a completely different human being, but the usual things happened that happen to most of us as we get older. My weight became slightly less predictable; I wasn’t always exactly the same shape from one month to the next, and eventually I started experimenting with a straighter cut through my casual trousers and jeans, partly because I wanted more room and partly because I was interested in what changing the proportions would do.

And I liked it.

Actually, I really liked it, because suddenly I had trousers that still looked tailored and considered but didn't depend on me being precisely the same shape every single morning. And then when I did the same sort of thing with my jackets, keeping the shape but allowing them to sit a little more easily around me, I realised I’d found something that probably suited the man I am now better than the way I’d been dressing the man I was ten years earlier.

I think that is a much more useful way to think about dressing in your 40s. Not, “Am I too old for this?” But more like, “Does this still work for me?”

Because sometimes the answer will be yes.

If you’ve always looked fantastic in a leather jacket, why would hitting your forties suddenly change that? If you love trainers and they match the way you dress, keep wearing them. If you’re the bloke who has always worn a colourful shirt and everybody knows you for it, I certainly don’t want to be the person who puts you in pale blue or white and tells you to behave yourself.

But there will probably be other things where the answer is a firm “no”, and I think most men can know exactly what some of those things are if they’re willing to pay attention to their instincts.

You put something on, and technically it still fits, but you don’t quite like yourself in it anymore.

That’s an interesting feeling because it isn’t necessarily about getting older, and it certainly doesn’t mean you need to start dressing older. Sometimes your taste has simply moved on before your wardrobe has caught up.

Your life might have moved on too.

This is the bit I think gets overlooked when we talk about men and age, because your 40s can be an odd period where, professionally at least, you might be operating at a completely different level than when you bought a lot of the clothes still hanging in your wardrobe.

Perhaps you’re running the company now, or you’ve made partner. It could be that people who were once your peers now work for you, or you’re walking into rooms where the decisions have become bigger, the numbers have also gotten bigger, and the consequences of getting things wrong have become considerably bigger too.

Does that mean you need to wear a three-piece suit every day? Of course it doesn’t.

If anything, one complication for men at this stage of their careers is that the old uniform hasn't disappeared ss changed. I’s changed. It used to be fairly easy - you got promoted, you bought better suits. You got promoted again, you bought even better suits. There were nuances obviously, but you basically knew where you stood.

Now you can be sitting opposite somebody running a company worth hundreds of millions, and he’s wearing jeans.

Which sounds wonderfully liberating until you realise you now have to work out which jeans, with which shirt, under which jacket, with which shoes and whether the whole thing says “successful man who understands exactly what he’s doing” or “I couldn't find my hoodie this morning”.

This is why I keep coming back to life rather than the age.

When I start working properly on somebody’s wardrobe, I’m not thinking, right, 47 years old, therefore three navy jackets, two pairs of grey trousers and absolutely no fun after dark. I’m trying to understand all the different versions of the individual that needs dressing.

There’s the man who has the important meeting. The man who has a normal day in the office.

There’s the man taking his wife out for dinner and the man always flying somewhere for work.

There’s the man going to Wimbledon, or a wedding, a black-tie dinner, or sitting in a pub on Sunday afternoon having absolutely no desire whatsoever to look like he’s just left a board meeting.

They're all variations, modes even, of the same person.

And I think when your wardrobe starts working properly in your 40s, it should be able to move between all of those different versions of you without any of them feeling like fancy dress.

That takes more clothes, by the way, not fewer.

I want to make that distinction because there’s a slightly tiresome idea floating around menswear that the enlightened man eventually achieves some sort of wardrobe nirvana where he owns twelve perfect garments, all of which apparently combine into 764 outfits and presumably wash and press themselves overnight.

That’s lovely if your life works like that, but most of the men I know don't have lives that work like that.

They need summer clothes and winter clothes. They need proper suits and casual jackets. They need jeans, trousers, shirts, polos, knitwear, coats, shoes, dinner clothes and things for those awkward occasions where nobody will tell you what the dress code actually means but everybody will of course know that you got it wrong.

So I’m absolutely in favour of a comprehensive wardrobe, but what I’m not in favour of is a wardrobe full of random solutions to old problems.

This is something I see constantly when I visit a new client at home because we’ll start going through what he owns and almost every garment he shows me begins with the words, “I needed this because…”

“I needed this for a wedding.”

“I needed this to go to the cricket.”

“I needed this because we had a conference.”

“I needed this for a holiday.”

After a while, I’m standing in front of a wardrobe containing thousands and thousands of pounds worth of perfectly decent clothes, and somehow the client still feels like he’s got nothing to wear.

That’s not because he needs to buy less - he probably does need to buy more.

He definitely needs to stop buying things in isolation, stop making reactive purchases and start filling the gaps deliberately and in a considered way so that, over the next two to four seasons, the wardrobe begins to make sense as a whole.

And maybe that’s the thing I’d encourage you to do if you’re reading this because you searched “how should a man dress in his 40s?” and expected me to give you a definitive shopping list.

Don't start with the shopping list. Start with your diary.

Actually look at the next month of your life and think about what you need to be dressed for, because I suspect that will tell you so much more than your age ever could. Look at the meetings, dinners, weekends, travel and the events you already know are coming and the normal boring Tuesdays and Wednesdays in between, because those all count too.

Then look at your wardrobe.

Can it deal with all of that?

Not just technically - I don't mean, “Yes, Roberto, I own trousers.”

I mean, do you have the clothes that make you feel properly dressed for those situations, in the shape you are now, at the level you're operating at now, without having to stand there every morning trying six different combinations before giving up and wearing the same thing you wore yesterday?

If you do, brilliant. But if you don't, that's where I'd start.

I don't think turning 40 means you should start “dressing your age”. To be honest, I’m not even sure what dressing your age means anymore.

But I do think you should dress your life, your body, and your personality as they are now, and perhaps give a little thought to where all three are heading next because, if we're lucky, none of us stays exactly the same for very long. I mean in terms of career progression, etc, not your waistline. We don’t do waistline progression!

Actually, having thought my way through all of this while writing it, maybe that's why this question becomes so common when men hit their 40s in the first place.

You're not suddenly worse at buying clothes - but maybe you've simply changed enough that the wardrobe which used to make sense doesn't quite make sense anymore.

And that’s a much easier problem to solve than trying to work out whether you're now officially too old to wear trainers.