The midlife man’s guide to getting jeans right – and why to avoid the dreaded boot cut

Andy Warhol insisted he wanted to die in his. Yves Saint Laurent’s only regret was that he didn’t invent them. And the late, great Diana Vreeland – ex-Vogue editor and peerless arbiter of taste – insisted that blue jeans were the most beautiful invention since the Venetian gondola. 

She’d perhaps be raising a pencilled eyebrow, then, at the images of Brad Pitt over the weekend attending the Las Vegas Grand Prix in a rather shapeless pair. Let’s be honest, Brad Pitt can wear a Teletubby costume and still look fantastic, because he’s Brad Pitt, but it does raise the question of which kinds of denim a man should opt for at different ages.

Pitt, at 59, has been undergoing something of a style renaissance in recent years; experimental designers and bold fashion choices, from skirts to pastels. More power to him. Jeans are as American as apple pie and the most democratic item of fashion probably ever invented. 

There are some style arbiters who look exceptional in denim; Ralph Lauren, the embodiment of preppy Americana, in a beaten-up leather jacket and great jeans. Tom Ford, sharp as a tack in a white shirt and sleek denim. 

Or even the more run-of-the-mill Gary Lineker, who at 62 looks pretty damn good in his workaday denims. 

While we’re yet to see the King in a pair of 501s, the younger royals – the Prince of Wales and his brother, the Duke of Sussex – are rarely without them. But what guidelines should men adhere to? 

Take pointers from tailored trousers

“We worked to make denim very sophisticated and elevated,” says Brunello Cucinelli, the maestro of Italian finesse. The designer, who recently celebrated his 70th birthday, is a prime example of how sharp a fellow of a certain vintage can look in jeans, and make them smart too; a precise cut that mirrors the sharpness of tailored trousers, and attention to detail in terms of plackets, turn ups and a smart belt. 

Worn with a jacket and shirt, they’re casual and easy but hold their own in a formal setup. Cucinelli advocates lighter washes or diverting from classic blue entirely in favour of charcoals and dove tones. Pointing to his denim jeans, he gestures; “denim is a key part of a man’s wardrobe”.

The most problematic silhouettes

Nigel Farage, currently spending his days in the I’m a Celebrity… jungle, has been ridiculed on the show for his overly exaggerated high-waisted trousers, hitched curiously up his torso. He’s not in jeans, but it demonstrates an issue men grapple with in terms of cut and fit of trousers. 

Shape is the deciding factor in all things related to jeans. Narrow and skinny looks en pointe on the likes of Sir Mick Jagger et al, but avoid if you’re anything other than reed thin; denim is forgiving but tight jeans show every bump in the road. Likewise – and apologies in advance for being indelicate – they highlight what God gave you.

The opposite number are saggy, baggy jeans, which is often the option that most men go for because they seem easy and don’t require a great deal of thought, but the issue here is the lack of silhouette not doing much for the frame. They also don’t balance well with a jacket. The halfway house – the dreaded boot cut – is also questionable. The dated style from the 1990s carries connotations of regional nightclubs and shoes like leathery pitta breads. 

The most flattering shapes

Straight-cut or slim-cut are generally the average man’s friend here, the former more so if you’re in any way reluctant to opt for anything too figure-hugging. In terms of shape, be wary of lengths that require anything more than a crisp turnup, because thicker varieties will only serve to shorten the frame. 

If you’re particular, there’s also the option of selvedge – a Japanese process whereby the fabric contains a tight weave on the edge of the denim, meaning it doesn’t fray (literally “self-edging”) and there’s a greater weight to it. The stiffness of the fabric means that it gives more structure and form.  

The right tone

From there, it’s a question of wash. Denim connoisseurs – there are entire tribes who scour the backstreets of Tokyo and Los Angeles – have myriad opinions on gradients and fades, but, generally, darker is considered better. The other issue with light blue washes is that, unless they’re neat and straight-legged, baggier varieties fall into the “dad jean” category, a rather 1990s affectation that’s to be avoided unless you’re doing so with Gen Z irony. 

Avoiding light shades isn’t a hard and fast rule – see the debonair Cucinelli in his chalk-tones – but it’s an approach one doesn’t need to think about as much. Neutrals can also look great and there is also a certain Left Bank flair to crisp white jeans – see Pierre Maheo, creative director of Saint Germain-based brand Officine Générale. Just avoid the vin rouge. 

All in the detail

As for detailing; keep it simple. Unless you’re a rock god with the renegade attitude to match, ripped, distressed, studded or overly intricate iterations of denim are best left to Eurotrash-tastic lotharios. There’s a rightness and cleansing sense of simplicity to a great pair of jeans, one of the most enduring clothing items since the early days of the West Coast pioneers, that doesn’t need fiddling with.  

Three ways to style jeans

Selvedge denim jeans

Cotton twill jacket, £110, Cos; Wool and alpaca jumper, £77, Arket; Japanese selvedge denim jeans, £212, Sunspel; Leather shoes, £190, Duke & Dexter 

Blue jeans

Wool jacket, £167, Percival; Cotton t-shirt, £14.90, Uniqlo; Stone washed jeans, £125, Asket; Suede shoes, £170, Uniform Standard 

Black jeans

Wool coat, £450, Gant; Lambswool polo, £90, A Day’s March; Levi’s 501 jeans, £72, John Lewis; Leather boots, £149, Massimo Dutti