Why Shopping For Clothes Gets Harder After 40

Shopping for clothes didn’t suddenly become harder because you’ve forgotten how to dress. Perhaps the rules changed around you.

One of the things I’ve noticed, having been a bespoke tailor for as long as I have, is that there comes a point with a lot of men where buying clothes seems to become really difficult, and I don’t mean difficult in the sense that there aren’t enough shops or there isn’t enough choice because, if anything, there’s probably far too much choice nowadays, but more that something which used to be reasonably straightforward suddenly becomes this very annoying problem that gets pushed further and further down the list until eventually somebody sits in front of me and says, “Roberto, I just really struggle to buy clothes that fit or are in my style.”

And I hear that a lot.

Usually from new clients in their forties or fifties, sometimes younger, sometimes even older, and nearly always from somebody who is actually much more confident in every other part of their life than they were twenty years ago, which is why I’ve always found it quite fascinating because you’d think the opposite would happen, wouldn’t you? You’d think that once you get to a certain age, you know exactly what you like, exactly what you don’t like; you’ve done the experimentation and made all the mistakes already, and you’ve stopped worrying about whether whatever you’re wearing is fashionable that particular month or season.

You’d think buying clothes would become easier, but for a lot of people it doesn’t.

Now, the obvious answer is to say, well, you’ve got older and your body’s changed, and obviously that can be part of it because none of us stays exactly the same shape forever, although I do have some clients who seem determined to prove me wrong on that and have somehow maintained almost exactly the same measurements for twenty years, which I’m insanely jealous of given my own weight feels like it fluctuates more frequently than I change my socks.

But for most people, yes, things move around a little bit. You might be broader than you were, your waist might be slightly different, maybe you cycle now and suddenly none of the trousers in the shops will go over your thighs, or perhaps you’ve started going to the gym (I mean properly, with a personal trainer and everything) and jackets that once fitted quite nicely across your shoulders now feel as though somebody has shrink-wrapped you into them.

That’s totally normal. What I don’t think is normal is the way we immediately assume that means we’re the problem.

I’ve had this myself over the last few years because I don’t dress in exactly the same way that I did when I was 40, and actually looking back at photos I wouldn’t want to. I used to tailor things much closer to the body, particularly trousers, because that was the silhouette I liked at the time and it suited the shape I was then, whereas now I’ve gradually moved towards a straighter trouser, a little more room through the leg, jackets that still have shape but aren’t ultra fitted at the shoulders, chest and waist… tailored but comfortable is my zone now.

And I find that much easier to live in.

The funny thing is that I probably look better in those clothes as well, or at least I think I do, because they look less tied to a particular moment in time (or my body shape!) and I’m not spending half the day thinking I really need another half inch put into the thighs.

So I don’t think this is really about getting older and somehow losing your sense of style.

If anything, I think you become more aware of what suits you, but your tolerance for things that don’t work becomes much lower.

When you’re 25, you can spend an entire Saturday wandering around shops trying things on, and if the jeans are slightly uncomfortable you buy them anyway because you like them and convince yourself you’ll break them in and they’ll somehow become comfortable later, which of course they never do.

By the time you’re 45, the thought of spending a whole Saturday afternoon traipsing around the shops is laughable.

You’ve been working long hours all week, you’ve got family things going on, there are a dozen jobs at home you haven’t done, and the idea of spending four hours walking around Oxford Street looking for a pair of trousers that may or may not fit properly induces the mother of all migraines at the mere thought.

And then we decided online shopping was going to solve all of this.

Which, in theory, it should, right? You sit on the sofa with your iPad or MacBook, order a few things, they arrive within a couple of days, and your problems are solved.

Except what actually happens is you order three different sizes because you no longer have the faintest idea what size you are, one brand thinks you’re a medium, another thinks you’re an XL, one pair of trousers fits your waist but seems to have been designed for somebody with legs like drinking straws, another pair has so much room around the seat that you look as though you’re smuggling a cushion, and then all of it sits in the hallway for two weeks because you haven’t had time to send it back. And of course you pass the return window and are then stuck with it all.

So we haven’t really eliminated shopping; we’ve just moved the changing room out of the stores and into our home, and given ourselves some extra admin to do afterwards.

Then you’ve got the other problem, which I think is probably bigger than most people realise, and that’s that nobody really knows what they’re supposed to wear anymore.

When I started doing this, most of my business clients had a pretty clear idea of what workwear looked like because they wore a suit.

That was it.

The suit was either navy or grey, and on certain days you might have felt particularly adventurous and worn a pinstripe or subtle check, but you never woke up on a weekday morning wondering if jeans and a polo shirt were too casual for a client meeting at 11am.

Now we’ve got smart casual.

And no, I’m actually not biased because not only do I make suits for a living, but I make a tonne of smart casual outfits for clients every season too. But I think we may have accidentally made getting dressed much harder in the process of trying to make it easier.

Because what does smart casual actually mean?

I’ve been doing this for over 20 years, and I still couldn’t give you one answer that would work everywhere.

Smart casual means one thing in a law firm, something completely different in a tech company, restaurants have their own interpretation, and then somebody invites you to something with “smart casual” written at the bottom and you immediately start trying to work out what everybody else might be wearing so you don’t show up looking underdressed or overdressed - which is an impossible target because guess what, they’re all wondering the same thing.

But a suit, for all the criticism it gets, is actually incredibly simple.

You put it on and get on with your day.

That’s what I’ve noticed most as my clients have grown older alongside me - they aren’t necessarily less interested in clothes, but they are much less interested in wasting time on them.

They don’t want to own 50 different outfits because somebody on Instagram told them they needed a capsule wardrobe consisting of 17 carefully curated shades of beige.

They just want things that work.

They want to open the wardrobe in the morning and know that the trousers fit, the jacket works with them, their shoes are comfortable, and if they suddenly have to go from the office to dinner somewhere they aren’t going to spend the journey home wondering whether they need to change or not.

And perhaps that’s why shopping starts to feel harder, because by the time you get to that point in your life you’re not actually looking for more clothes - you’re looking for fewer mistakes.

You know what annoys you now.

That shirt you bought because it looked really cool on the model on the website, but the collar has never sat properly, and it has too much fabric through the waist, so it’s been hanging there for 18 months, waiting for a day when the wardrobe fairy finally visits, waves her magic wand and makes it fit you perfectly.

The trousers that technically fit but you would never actually choose to wear because of the fabric or colour.

The impulse-buy jacket you keep moving out of the way to get to the jacket you actually really like.

After a while you start realising that having lots of choice isn’t particularly useful if most of the choices in your wardrobe are wrong.

And that, I think, is where quite a few men end up somewhere around the age of 40 or 50, convinced they’ve somehow forgotten how to dress when actually they’ve just become a lot more time-poor and far more particular about what deserves a place in their wardrobe.

Which I don’t think is a bad thing at all; you probably know yourself much better than you did 20 years ago, your life is almost certainly a lot more complicated, your time is infinitely more valuable and maybe clothes now have to do a bit more work for you than they did when you were younger.

So if you find yourself standing in a shop one afternoon wondering why nothing seems to work anymore, don’t automatically assume you’ve lost your sense of style.

You may simply have reached the point where you no longer want to put up with clothes that almost work.

If any of this has struck a chord and you’ve reached the point where opening your wardrobe in the morning feels more frustrating than it ought to, perhaps the answer isn’t another afternoon spent wandering around the shops hoping this time will be different.

One of the things I do with clients isn’t simply make a suit or a jacket. We spend time working out what your life actually looks like now, how you dress for work, for travel, for weekends, for dinners, for weddings and all those occasions in between, then gradually build a wardrobe around you rather than expecting you to build your life around whatever happens to be hanging on a rail that season.

Because when your clothes fit your body, your personality and the way you actually live today, getting dressed becomes wonderfully uncomplicated again, and I think most of us have quite enough to think about without our wardrobe adding to the list.