For men, shopping in their teens and 20s may be a straightforward business.
But, as womenswear buyers are constantly reminded, time takes its toll. What was once fun and empowering – buying the latest labels at one's favourite store – is death warmed up decades later. Some are happy to relinquish responsibility to their wives. Others choose simply not to engage. That might explain the uniform of lumpy cargo pants and drab check shirts out in force at this summer's family gatherings, not to mention why my handsome younger brother is often attired in a shade best described as "sludge".
Fifty is a milestone regardless of gender. This year's crop includes George Clooney and designer Tom Ford, who both dress well in that Hollywood way. But if you're based in Hemel Hempstead, George and Tom aren't necessarily the most helpful role models. "I see the struggle of people ageing through their clothes," Roland Mouret, a fashion designer, says. "The guy who still wears really baggy jeans where you see a bit of the pants, or a [baseball] cap at 40, 45 – he is really pushing it. Or they wear a black jacket with a pair of jeans and pointy shoes and, okay, let's keep the shirt out. The notion for straight men is: shirt out means relax time."
Mouret's menswear line, MR by Roland Mouret, addresses the mature man with reworked standards. His colour choice, pleats and pattern cutting are genius. But the garments are simple and elegant.
Mouret says: "It's fascinating to be bombarded by men's fashion stresses. They know themselves as young people, but they don't trust themselves as mature men. Sean Connery understands it. They had their youth as sex symbols and they had to become men with maturity."
My brother-in-law, Ryder, gave up smoking in his mid-40s, hit the gym to counteract weight gain and at 49 looks buff and handsome (so he claims on Match.com). But his outfits are stuck in the early 1990s: black Levi's, Doc Martens or sports shoes, baggy T-shirts.
What doesn't help is that his local shops are chain stores that confuse being fit with dressing loud. Ryder drives a Jaguar XJ8; one might argue that he needs a wardrobe with similar high-calibre specifications.
Shoes are where most men shoot themselves in the foot. Call it the horror beneath the ankle. The difficulty of seeking a shoe when all you really want to wear is a pair of trainers results in so many heinous hybrids.
I introduced Ryder to Tricker's, a Northampton-based shoemaker established in 1829. He chose a pair of classic tan brogues, which would be good with chinos and even better with jeans. At Russell & Bromley we found a sneaker substitute in Sebago deck shoes, a summer all-rounder. Immediately Ryder looked more pulled together, with no change to his clothes at all.
"Older men fall most foul in the casual arena," the Barbour menswear design manager Gary Janes says.
"No movie star wore casual clothes better than Steve McQueen. Emulating his approach to dressing and combining timeless and classic garments such as trench coats, Barbour wax jackets, button-down oxford shirts, Levi 501s and loafers, is a great leap in the right direction."
As a photographer, Ryder's working wardrobe is full of denim. He wanted selvedge, to turn up the cuff and flash that connoisseur's stripe on the inner seam. Taking his budget into account we visited Uniqlo, where he bought two pairs of selvedge jeans, in indigo and dry black. For double denim chic, he sought out a jacket from Wrangler. And for quality English cool, we picked two shirts at Oliver Spencer, one check and one micro-herringbone.
I started getting compliments," Ryder says. "One woman yelled across a party because she was so excited about my brogues. The coolest guy in town asked about my denim jacket." A friend-of-the-family, Rob, is a couple of years past 50, has two boys under 10 and his wardrobe has been low on his list of priorities until now. Our first stop was Paul Smith's Sale shop on Avery Row in London, where Rob toyed with a parka, but bought a sweater in fresh summery purple and a youthful cut. Colour has endless potential for the older man. The right shade can brighten up a look and it's worth taking a little time to find what tones work.
Rob didn't expect to spend more than half of his £300 budget on an pair of brown Red Wing work boots but we'd tried a few shoes "just for fun" and these seemed to tick the box. It was a wise choice. They will last a decade, he'll wear them every day and we had just enough money left for a pair of jeans.
"Men underestimate the importance of fit," Brian Duffy, president of Ralph Lauren Europe, says. "Women know exactly what fits them and what compliments them, but guys don't think about it enough. It's about not wearing a shirt that's too big under a jacket that's too tight. And you put the whole lot together and it looks all wrong. How many guys buy things without trying them on?" Rob's preferred style of jeans is black Levi's 501. They're a design classic, but not for nothing are they known as "anti-fit" – they skim the body without being baggy but they don't cling.
For a modern sense of versatility, blue trumps black every time. Levi's has a broad range of fits, and the 504 standard gave Rob a slimmer, sleeker silhouette. "They take 20 years off him," his wife told me later.