How to dress with joy, elan, exuberance and carefully-managed extrovertism — no matter how old you are

A wardrobe consisting of the perfect balance of colour, character and joie de vivre might be hard to achieve, but is worth striving for. Simon Mills finds out how it’s done.

Here’s American Stanley Tucci, actor, writer, epicurean and leafy-south-London resident, in a proper zinger of an autumnal ensemble; pale-blue, windowpane-check suit in best Harris tweed, dark-blue, polka-dot scarf tied loose and louche around his neck, a navy linen flat cap at a rakish, baker-boy angle atop his head.

Stanley Tucci, a man who can carry off almost anything.  (Photo byDave Benett/Getty Images)

New York-born, 100% Italian and total Anglophile, Mr Tucci is unafraid of clashing spots and squares or bold, tone-on-tone arrangements. His popping colour choices are zesty and uplifting, but never comedic, lairy or attention-seeking. He pairs silks with wools against cotton poplin and merino with stylish abandon. On the television, he’ll team a happy, Pinot Noir foulard with a yummy Neapolitan sauce. In the summer, he may go confidently sockless in that easy, freewheeling way that only summering Calabrian men can.

At 63 years old, Mr Tucci’s au courant-conscious, yet age-appropriate clobber has sprezzatura, snap, style and sartorial joy. He is dressed for pleasure — yours and ours, but mostly his own.

This joie de mode may be a hard look to pull off at any age (and a very easy one to get wrong), but when the clocks go back, the skies turn grey and the nights draw in, dressing with joy, elan, exuberance and a carefully managed extrovertism can be an essential tool for winter survival.

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For inspiration, look to the British men who really know how to do winter and have a spring in their step even when there’s a bite in the air: take Jeremy Irons and Jarvis Cocker. Ask tailor Jeremy Hackett to name Britain’s most joyfully dressed man and he won’t hesitate: ‘David Hockney, who appears as if he couldn’t care less and yet…’ Mixing checks and stripes, seersucker and tweed, tradition and wit, American preppy and English gent, Mr Hockney’s look manages to appear simultaneously thrown together and immaculate, the co-founder of British gentlemen’s outfitter Hackett observes — it is both a work of art and a live-action cartoon.

David Hockney. (Photo by Aurelien Meunier/Getty Images)

Perhaps in a nod to the great artist’s delightful rule-breaking, one of Mr Hackett’s recent creations — made bespoke at his Savile Row atelier — was an exercise in modern, gentlemanly joy. Finding a grey, flannel wool fabric swatch he liked, but vacillating between a plain, chalk-striped or checked variation for his latest three-piece, he decided to go with all three. ‘Checked jacket, plain waistcoat and striped trousers. For a bit of fun, I had the tailors run the stripe on the trouser turn-up horizontally, at right angles to the leg stripe,’ describes Mr Hackett. During its debut London pavement outing — worn with handmade gold cufflinks that celebrate his beloved dog Harry and a rotated-dial, Historiques American 1921 Vacheron Constantin driver’s watch — this delightful rule-breaker of a whistle literally stopped traffic. On Jermyn Street, two Japanese menswear groupies jumped out of a taxi to take photographs and enquire of the suit’s provenance. ‘They particularly wanted to know where I got my turn-ups done.’

‘It’s difficult,’ reflects Mr Hockney and Mr Hackett’s mutual old friend, interior designer, generation-spanning fashion plate and enthusiastic trouser bottoms turner-upper Nicky Haslam. ‘Past a certain age, you can’t be too bright and fashionable, but you can’t be plain and minimal either. Plain looks a bit grim and depressing. Less is morbid.’

Mr Haslam, whose interiors are known for their bold and sumptuous colour, has a personal mood board of ‘honey, ginger, bright green, sky blue — and one hard and fast rule. No shorts on anyone older than 15’. He notes: ‘I don’t try to look fashionable, but I will be up to date. I see what the young are wearing and do my own, not-too-obvious version. My uniform is now plain denim trousers with a sort of boxy chore jacket. If you keep it simple, then you can wear a bright-yellow T-shirt underneath.’

William Gilchrist, the greatest living Englishman stylist, can count the Rolling Stones, Josh Hartnett and Jude Law as clients. Dressing Mick Jagger for the stage, he admits, requires a cranking of the joy factor up to a luminescent 11. ‘When you are trying to communicate to an audience of more than 80,000, many of them far from the stage, you have to make sure that you can be noticed,’ explains Mr Gilchrist, who kitted the band out in hi-vis, primary block colours for their Bigger Bang tour (and many more), but would advise against us civilians — with substantially smaller audiences and probably larger waistlines — trying to copy the Stones’s style.

Fast fashion: designer Nick Ashley favours the motorbiking, Goodwood Revival mode. Photo by Richard Young/Shutterstock

Joy in one’s wardrobe by way of colour can be found, the stylist suggests, by visiting the rusty/gingery Oliver Spencer chart or Brunello Cucinelli’s jet-set palette of comfortably off-greys and baby blues, rather than the more obvious rainbow spectrum of the children’s television presenter. ‘Play with lights and darks,’ he advises. ‘Blend and contrast fabrics. If you are going for pops of colour, do it in your socks and cashmere or merino knits — not your bi-focal frames.’

Mr Gilchrist himself favours a sober, but immaculate mix of double-breasted Italian suitings in navy blue, fawn and chocolate brown. He adds Continental jouissance with pocket squares and a gold fob chain looping from lapel to buttonhole. More life comes from what he calls ‘scarfage’ — a multi-hued, Kenyan kikoy, which he drapes under his coats, sans knot, leaving the ragged, tasselled ends to poke out like a flapper skirt.

‘Be wary of turquoise, purple and salmon,’ the stylist continues. ‘Canary yellow is particularly harsh and unflattering against a sallow complexion.’ Red trousers are, apparently, acceptable (let us pause briefly as Country Life readers everywhere breathe a deep sigh of relief), ‘but stop right there with the colours — a classic navy blazer and plain shirt on top, perhaps, and don’t be tempted to add, say, a mustard waistcoat or a pair of lime-green spectacles. Remember, one Palladian building is beautiful,’ Mr Gilchrist warns. ‘A whole Palladian town is a bit much.’

He is right about exercising caution around bright colours. Primary tones worn by the older generation are thought to be part of a later-life peacocking process that kicks in when a man stops getting ‘noticed’. The attraction reduction is compensated for via zany spectacle rims, fun waistcoats and pink socks (the cast of Antiques Road Trip are big on this).

If you must wear really bright colours, try cobalt blue. Endorsed by everyone from Sir Terence Conran to artist Yves Klein, this happy tone was made famous in the US by New York street photographer Bill Cunningham, who cycled the streets of Brooklyn and Manhattan, 35mm lens slung over his shoulder, aways donned in a traditional bleu de chine chore jacket.

The late New York photographer Bill Cunningham sporting his trademark bleu de chine chore jacket. (AP Photo/Richard Drew, File)

As worn by French labourers during the 20th century, the distinctive cornflower colour of the workwear classic set off Cunningham’s brown eyes and playful smile, bringing joy to everyone he stopped to pose for a snap. An old French workwear outfit called Le Laboureur, in the south of Burgundy, has been making excellent blue chore jackets since the 1950s. They now also come in green and red.

‘I heartily approve of all that Sloane/antique-dealer chic stuff,’ says perennially fussy dresser and style writer Peter York. ‘I do like happy colours, too, but I would avoid any item of bright clothing that might be considered an opening gambit, a conversation piece or a style that might cast you as “a bit of a character”.’

Mr York finds sober, judiciously selective joy at Cordings on London’s Piccadilly, ‘where they have corduroy trousers in every conceivable colour, as well as all elements of the classic British town-and-country wardrobe; tweed jackets, preppy shirts, seersucker, cord and waxed cotton, in the best and time-honoured tones. Chosen carefully and worn correctly, every one of these items will show that you belong’. Yet he adds a cautionary note: ‘Worn all together, pink trousers with a Henley stripe blazer, a Panama hat and a pair of “Hot” and “Cold” novelty cufflinks might have the opposite effect. You want to aim for Bill Nighy in Mayfair, not Tim Nice-But-Dim in Fulham.’

Is there room for colour, razzle-dazzle and eccentricity on more formal occasions — for example, with black tie or a morning coat? ‘As one gets older, social life might become more limited — often only balls and wakes — but that’s no reason to slack off, clothes-wise,’ believes Mr Gilchrist. ‘Black is ageing, so keep your old classic tux and midnight-blue lounge suit at the back of the wardrobe, ready for dinner-jacket nights and funerals. The rest of the time, have a bit of fun.’

‘After 50, somewhere between bereavement and bingo is where a gentleman’s trousers should be,’ he concludes.

Getting it right: The men who carry joy in their pockets

Richard E. Grant 
The actor is master of the spring scarf, the blue-on-blue-on-blue summer ensemble and the joyous winter waistcoat

Richard E. Grant no longer demands booze, but he does demand great clothes. (Photo by Joe Maher/Getty Images)

Norman Foster, Baron Foster of Thames Bank
Architect of his own wardrobe, no one wears pink tailoring and polo necks with quite as much panache

Ben de Lisi
The former dressmaker to Diana, Princess of Wales knows how to mix madras with mature tailoring, street styles with Savile Row and sturdy British footwear with all-American seersucker

Jasper Conran
Tangerine knitwear, canary-yellow socks and snooker-table-green tailoring come together with a bravura ease, wit and confidence for the British designer

David Hockney
Banana-yellow Crocs… with tweed? When you’re the world’s greatest living artist and a work of art yourself, any combination is possible

Nick Ashley
Every day is a glad-ragged, Goodwood Revival sort of day for Laura Ashley’s revved-up, motorbiking designer son

This article appears in Gentleman’s Life section of Country Life’s 6 November 2024 issue.