The Regent Guide to the Mid-Life Crisis

The often-parodied concept of the mid-life crisis is easy to dismiss: it’s such a part of our popular culture that many men think they’re far too self-aware for it to happen to them. But behind the caricature lies something more subtle and complex, and the mid-life crisis can sneak up on you in unsuspected ways

In this blog, we delve deeper into what this fabled time of flux really means, aiming to offer some advice along the way in order to show that getting older doesn’t have to mean giving up – far from it, in fact…

Beards, Boats and Bellies: Busting the Clichés

We all know theclichés. You buy a fast car, motorbike or even a boat. You grow your hair out;you try something new with the facial fuzz; you can’t quite ditch that beerbelly that’s been creeping up on you. The mid-life crisis has beenwell-documented and had the mickey taken out of it (often rightly so) fordecades now – we’re particularly fond of the Penguin spoof The Ladybird Book of the Mid-Life Crisis, which is perhaps a good place to go to read all the clichés summed up in a single place.

But what all this noise can do is cover over something that’s a little more complex, intricate and subtle: something that, true to its name, can throw men into a real point of difficulty and depression. So let’s do away with the clichés for the time-being and allow ourselves to look at the mid-life crisis head-on, and work out what’s going on.

The psychoanalyst Elliot Jacques put his finger on the pulse in 1957, when he gave a paper outlining the senses of concern and depression we can feel – typically between the ages of about 35 – 65 years old – thanks to the increasingly keen sense of our own ageing and mortality that we experience at these points.

It’s a classic: as a teenager and through your 20’s it feels like you’re on an upward trajectory, and you’ve still got your life ahead of you. When you reach your mid-thirties or early-forties, you begin to get a sense that you’re ‘deep in it’ now: you get whacked by a sense that things haven’t gone as planned, that life is somehow happening differently to your designs, that you’re getting pigeonholed into a version of yourself you’re not sure you’re that keen on.

Facing the Facts

Feeling like the best bits are behind you, or that things haven’t gone the way you imagined, are only a state of mind. And luckily, minds can be changed. Indeed, the only real factual basis to a mid-life crisis is that of your age: yes, it’s true you’re older, and certain things might seem unavailable to you now, because that’s natural – we make the transition from yelling and screaming and acting like children into adults seamlessly enough (well, mostly, at least!) and yet we don’t bemoan the lack of being able to act like a baby. Rather, we look forward to all the new things our adulthood will afford us. The mid-life crisis can be seen as another, exciting version of this kind of transition: the opening of a new door, rather than the closing of one.

Indeed, in many cultures, the older you get, the wiser, the more valuable you are. Our Western culture is obsessed with the cult of youth, but this is only a relatively recent invention. But the Greeks, the Native Americans, and the Indians are just three cultures that value and respect their elders, viewing them (rightly so!) as having accrued more experience and learnt life’s valuable lessons that can only be learnt with time. 

But, yes, we admit: it might be harder to pull off certain items of clothing as you get older. However rather than focussing on what you’ve lost, focus on what’s newly opened up to you: a lot of the time, men simply don’t realise all the new and exciting ways of dressing that are actually opened up by their progress through the ranks of age. Every week, we get men coming through our doors who are seeking, actively, to discover what might suit them better now they’ve reached a certain landmark age, and we take great pride and joy in showing them great brands and styles that are just as fresh, satisfying and cutting edge as what the kids are wearing.

The good news is that in his paper, Jacques highlighted that he’d identified the phenomenon of the mid-life crisis by studying artists, who often experienced this stage as an incentive to shake things up and produce some of their best work: the artists flipped the expectation on its head, saying that they’d been in a rut in their teens and 20’s, and now they were finally getting free. We think this is closer to the truth than all the clichés. The mid-life feelings you get, are, basically, totally normal: it’s just a new phase in your life, and an opportunity to do things differently.


David Bowie understood this intuitively. He is a tremendous example of someone who saw the process of ageing as a chance to unlock new aspects of his personality, and often to re-do himself completely. The trick with this is to give it some thought – to not panic – turning your mid-life crisis into a mid-life clarity. Bowie was an artist: thinking about his identity carefully was integral to his project. You can’t change overnight: it’s a process. And it’s this process we’re here to help with.

When you want to re-take the reins on life a little bit, your look – your clothing and your style – is such a great place to start. We should never underestimate how radically the way we dress each day can affect the way we think and feel about ourselves. We’re talking from experience, here: Jason, the boss at Regent, works hard to vary his look to suit what the day needs, even in lockdown. One day he might be in a pair of jeans and a cashmere v-neck, the next in a full suit: it all depends on what he needs from that day, e.g. to feel whip-smart and ready for anything or, if he’s going a little more casual, to still feel like he’s not just collapsing into a t-shirt, or a hoodie – that even his casual is great quality and puts out a positive image to the world.

Styling It Out

So, here are some gentle nudges, some tips from the experience we’ve gleaned along the way. 

Try starting plotting your route through this mid-life crisis by asking yourself: who and what do you want to become? As opposed to beating the inexorable path towards Dad-dom and quittingly donning a pair of slacks and a fleece, try casting about for some inspiration. Who out there your age or older do you admire for the way they look and dress? Is there a musician you admire? An actor, a sportsman? Jason personally always has Steve McQueen on one shoulder, and James Bond on the other, helping him work out what to wear. Rock stars like Nick Cave and David Byrne are great inspirations for the way they wear suits in an approachable and almost informal way, whilst a character from a film’s wardrobe – such as Colin Firth in A Single Man – can be a great thing to study.

Rather than buying a whole new wardrobe spur-of-the-moment and regretting it later, try buying one new thing every month or so. And buy a few great, well-made and classy things rather than go for cheap variety: it’s easier on your wallet in the long run. For example, going for a pair of Cheaney shoes that are re-soleable and timelessly designed over a pair of cheap stuck-on-sole highstreet shoes will have you filled with pride and feeling great about yourself every time you wear them. Clothing can be aspirational – you dress like who you want to be. It’s like playing sport against someone better than you – it raises your game. You want to buy stuff that’ll last the rest of your life – that you can pass on to your kids. At this stage in life, after all, you are worth it. 

A capsule wardrobe is a great way to neutralise the crisis: owning a core group of garments that you know all go great together, whatever the weather, equals a no-fuss approach to looking amazing every morning. Block colours are a good idea: timeless, classic, un-flashy. Owning a great white Oxford button-down is a staple, for any day of the week, to build an outfit around: pair that with a fine wool vee or crew neck and you’re instantly in the zone. A pair of Edwin loose- or regular-tapered jeans with some Redwing boots is a nice way to carry a bit of edge without seeming like you’re trying to dress down your age, too. Think Ivy League: chinos, blazers, button-down shirts: these are timeless styles that would look too precocious on a twenty-year-old, but which a better-established gent can rock with ease.

The rules are good to know, but it doesn’t mean they can’t be broken. If you do want to get a floral shirt and a leather jacket, get small floral print (these are much more flattering and Italianate, way classier) and an Aero Leather jacket – again, see Steve McQueen for the way an older gentleman can pull off a piece like this. Mid-life doesn’t mean you can’t be spectacular: it’s just that what is spectacular changes from more showy, outward displays of edginess or idiosyncrasy, and becomes about how well a man knows himself, how he affords himself to be a bit more brave, a bit more bold, a bit more classy than his younger self would ever dare, because (and we often forget this), when you’re younger, you tend to be more insecure. Middle age is about feeling secure enough to dress well and invest in the best.

Personal Styling at Regent

As part of our one-stop-shop ethos, Regent offer free personal styling appointments in order to get to know you, learn about where you’re at with you current style and image and to help develop and re-think it, or simply to push it further, depending on what you’re after. We’ve worked with people on whole-image revamps as well as focusing in on individual aspects, such as the shoes or shirts you wear. We believe that true style is knowing who you are, so we place an emphasis on listening, discussion and collaboration.

We’ve been helping gentlemen steer clear and through mid-life crisis for over a decade, now, and Jason is passionate about showing people that it doesn’t have to be daunting – that is, first and foremost, an opportunity. Please don’t hesitate to get in touch – we’re even doing virtual appointments at the moment.

Finally, we can point you towards a couple of other folk who address the question of mid-life style with expertise, fun and sartorial savvy. Check out The Grey Fox blog, which caters for beautifully for men over 40; see TinTinFellow on Instagram for cool, tasteful ways to break the rules; follow The Sartorialist on Instagram for innumerable ways that gentlemen keep it incredibly cool as they get older; marvel over Giuseppe Santamaria’s inventory of well-dressed gents from Italy, New York, London and more in his In This Town books for urban chic. We’re proud supporters of the Distinguished Gentlemen’s Ride Charity, who support men’s mental health and the fight against prostate cancer.

The takeaway is this: it’s normal to feel like this, to go through this period of uncertainty, and if you feel a sense of loss of worth, the clothing and re-calibrating your look can be a great place to start. There are also loads of great books out there if you want to read further. If you’re really struggling with your mental health during this time, then do of course contact the great folk at The Samaritans – we know that sometimes great clothes can only get you so far.  

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