The seven style signs of a man’s midlife crisis

And last month they did. Not because of the report on the Iran war, but because the newsreader had the audacity to anchor ITV News at Ten wearing a pair of red trainers with his suit. He might have got away with it if not for a sneaky under-the-desk side-view. Viewers immediately took to X to vent their spleens.

“The absolute state of Robert Peston on ITV. Since when did it become acceptable to wear trainers with a suit?” guffed one keyboard warrior. Others mentioned his age. “Peston must be pushing 70 but he insists on wearing trainers with a suit, seriously Robert?” You could almost hear Alastair Burnet spinning in his grave.

But suggestions that Peston, in his convention-defying Nike Air Jordan 1 trainers in the Chicago colourway (red, white and black), was in the midst of a midlife crisis were misguided. The 65-year-old presenter has form when it comes to avant-garde garb.

Robert Peston’s red trainers sparked much online debate in recent weeks - Grant Buchanan/Dave Benett/Getty Images

Personal stylist and presenter of the Style Stories podcast, Lisa Gillbe, explains: “Robert Peston has what’s referred to as ‘the elite outsider look’. This is where elite creatives reject traditional professional standards. Personally, I like it, but a lot of people don’t and believe he should dress more seriously in the context of what he does.”

Indeed, it is not unusual for men of a certain age to have similar midlife-style wobbles. Commentators describe it as the male midlife makeover, or MMM. It is like a midlife crisis but less messy than an affair and cheaper than a Harley Davidson. It involves replacing all your regular garb – your jeans and polo shirts – with what you imagine to be a younger wardrobe. It often ends in disaster.

Gillbe cautions: “Trying to dress younger is the first mistake.”

Instead, she advises “dressing like the best version of you”. This involves buying better quality clothes, which fit properly. So skinny fits are not a good idea, particularly if you are carrying some heft around the middle. Likewise, exaggerated billowy cuts are also ill-advised, particularly for shorter men.

Actor Patrick Dempsey gets it right – sharp tailoring and quality clothes which suit his body shape - Jason Mendez/Getty Images

Gillbe recommends brands such as Oliver Spencer, Sandro and Wax London.

“Go for slim-straight dark denim jeans, smartened with an unstructured blazer,” she adds. “Work out what suits you and switch up a few items subtly. Don’t go out and get all that midlife crisis stuff. Start paying attention to quality.”

So, what exactly does a midlife-style wobble look like? It tends to fall into a handful of recognisable traps.

The sneaker pimp

There are trainers, and then there are trainers worn in the wrong context. When Rishi Sunak stepped out in Adidas Sambas with suit trousers and a shirt, the internet had a collective convulsion.

Gillbe puts it bluntly: “It was visually wrong. It was so jarring.”

Rishi Sunak’s Sambas moment – when trainers clash with tailoring, fashion coherence goes out the window

The problem is not trainers per se. Plenty of men wear them well. But when they clash with the rest of the outfit, they scream confusion rather than effortless cool.

“Don’t wear gym trainers unless you’re going to the gym,” Gillbe adds.

The trick is coherence. Trainers can work with tailoring, but only if the whole look has been designed around that contrast.

The careless wrister

Another curious midlife tic is the sudden appearance of wrist jewellery, worn with the hopeful conviction that it might function as a kind of silver bullet for coolness. A few leather wraps or jangling bangles are added and voilà – you have ascended.

Jeremy Clarkson drifts into this territory pairing an armful of the type of leather straps you buy from stalls in Tenerife with scruffy jeans and a checked shirt.

Jeremy Clarkson’s wristwear proves accessories can’t rescue an otherwise muddled look - Jeff Spicer/Getty Image

The problem, as Gillbe suggests, is that accessories cannot rescue an outfit that has not been thought through. “Have that separation between work and weekend,” she says. “Think of smart separates.” A bracelet can look deliberate and stylish, but only when the rest of the clothes are pulling in the same direction. Otherwise, it is just a last-minute attempt to bolt coolness on at the wrist.

Teenage icks

There is a fine line between looking relaxed and looking like you have just rolled out of student digs after a three-day gaming session.

Step forward Adam Sandler, who looks like he went to a Billie Eilish garage sale in 2019 and bought her entire wardrobe. The actor has built an aesthetic around oversized basketball shorts, hoodies and trainers. On him, it is almost a brand. On everyone else, it can look like a refusal to accept that adulthood has arrived.

Adam Sandler has made student dressing his signature – but it’s a risky look to copy - JC Olivera/IndieWire via Getty Images

Gillbe sees this frequently among men trying to recapture the wardrobe of their 20s. “I see a lot of middle-aged guys who dress like they’re still at university in hoodies, baseball caps and baggy jeans.”

The alternative is not boring clothes. It is simply better clothes. A well-cut pair of jeans, quality knitwear and a decent jacket will always beat the eternal-student look.

Hell for leather

Leather biker jackets are one of menswear’s most seductive traps. In the right hands they can look cool. In the wrong ones they can look like a midlife motorcycle breakdown.

Gillbe cites Jeff Goldblum as someone who can make the style work. “He is probably one of the most stylish people,” she says. “He’ll wear a leather jacket and make it look good because he’s Jeff Goldblum.”

The difference is confidence and consistency. Goldblum’s entire wardrobe leans theatrical and eccentric. Most men, however, are not Jeff Goldblum.

Jeff Goldblum shows how leather can work - TheStewartofNY/GC Images

Old hat

Few garments divide opinion like the baseball cap on a man over 50. Done badly and you look like a Hulk Hogan tribute act on the golf course. Executed well, it looks like a well-placed style motif. Jack Black and Spike Lee are just two of the stars who have experimented with a baseball cap lately – Lee exuded sporty ease, Black, well, didn’t.

Gillbe explains: “A baseball cap can finish off a look if it is considered.” The key is context. A cap thrown on with a tracksuit tips a man into retired-footballer territory.

“But if you’re wearing it with a sharp wool coat and some smart jeans, it can look really cool,” Gillbe adds. There is a golden rule, however. Don’t wear it backwards.

Jack Black’s cap-and-puffer combo veers into a ‘rolled out of bed’ look - MediaPunch/Bauer-Griffin/GC Images

Channelling Timmy Mallett

Bold colours can be thrilling. They can also make a man look like a children’s television presenter from the 1980s.

Even Brad Pitt, normally one of the safest style bets in Hollywood, occasionally flirts with the danger zone when experimenting with brighter palettes and eccentric tailoring. Colour works best when it is balanced with otherwise classic pieces. A bright knit with tailored trousers. A bold jacket with simple denim. Otherwise, the effect can feel costume-like.

The temptation for men in midlife is to throw everything into the wardrobe reboot at once, mixing colour, pattern, and unusual cuts. A touch of colour is good. Looking like Timmy Mallett is not.

Brad Pitt’s bold choice of blue velvet tipped from daring into costume - XNY/Star Max/GC Images

The try-hard

Daniel Craig has spent most of his career in sartorial transcendence wearing crisp tailoring, neat hair, and exuding Savile Row elegance. But his association with Spanish fashion house Loewe nudged him into more experimental territory.

At Paris Fashion Week in 2024, he appeared in a colourful knitted jumper paired with a neckerchief, a leather bomber jacket, billowing olive-green balloon trousers, tan suede boots and round yellow-tinted sunglasses. At an age when many men drift quietly towards Marks & Spencer, Craig looked like an extra from Mad Max: Furiosa.

Daniel Craig’s look at the Loewe Paris Womenswear Spring-Summer 2025 show proved that experimentation can quickly become overkill if it strays too far from your personal style brand - Stephane Cardinale - Corbis/Corbis via Getty Images

Gillbe says the issue is not experimentation itself. It is whether the style reflects who you are.

“It’s more about discovering yourself and what you enjoy wearing than trying to look younger,” she says. “Understand what works for you, then wear a better version of that.”

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