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The Knowledge

Are You Dressing Your Age?

Don't get caught with your mid-life crisis showing. Follow our tips for age-appropriate dressing

It’s easy to think that dressing well is a skill that, once mastered, is retained for ever. In fact, it’s a little more like playing a musical instrument or learning to speak a language – over time, you need to practise, revise and continually relearn. The leather jacket and band T-shirt you wore to Glastonbury in 2006 will not serve you well in the boardrooms of today. That bright blue blazer that made you look dazzlingly Mediterranean at your cousin’s wedding will give you a rather ghostly aspect by the time you’re in your sixties.

On the other hand, it’s important not to jump the gun and sentence yourself to a lifetime of drab flannel suiting. A lot of designers make a real effort to produce exciting, pattern-drenched, sports-influenced pieces for the young men of this world – so you should make the most of them while you can. At any age, the key is to strike a balance. The following guidelines are designed to explain how this works as your years become ever more golden.

  • Robert Pattinson, New York, May 2015 Splash News/ Corbis

In former times, your twenties signified a coming-of-age period. This might have been the decade where you bought a house, got a steady job and, if you were really serious about growing up, became a parent. Now, of course, it’s a confused, mystically extended adolescence, in which it’s never quite clear whether you’re supposed to be being responsible or having fun. In this sartorial limbo, an outfit such as Mr Robert Pattinson’s, above, strikes a balance between “put together” and edgy, and is a great starting reference for any twentysomething looking for clothes to take him through the working day and beyond. The restrained colour palette of white, navy and midnight blue looks mature and tasteful – but he’s kept it appropriately young with militaristic touches in the bomber jacket and combat boots. The result is a refined take on casualwear which, if replicated, will make you seem both on the pulse and worth listening to (though if you want to put the emphasis on achieving the latter, you could lose the beanie).

What to Wear

  • Officine Generale Ben Shell Bomber Jacket

  • Tricker's Roy Pebble-Grain Leather Boots

Brands to look out for:
A.P.C, AMI, Acne StudiosCommon Projects

Your signature fragrance:
Santal 33 Perfume Oil, 30ml, by Le Labo

  • Hidetoshi Nakata, Paris, June 2015 Laurent Vu/ SIPA/ Rex Features

However arrested your development may be, by the time you hit your thirties you will need to invest in some tailoring. This is not just to make you look more businesslike – it will also make life easier as you juggle the responsibilities it increasingly seems to be throwing your way. A well-fitted navy suit is appropriate for almost any situation and makes getting dressed in the morning almost effortless. But it can be fun, too – as you’re still in your physical prime you can make like Mr Hidetoshi Nakata and opt for adventure in the suit department. In this image, he’s gone for a denim suit (pairing with sneakers – this is also now officially allowed, as long as they’re clean and white), but he could equally have opted for an eye-catching colour such as beige or petrol blue. To look a little bit more like him, keep an eye on Parisian brands such as Valentino and Officine Generale, both of which offer canny and refreshing new twists on the tailoring template each season.

What to Wear

  • Tomas Maier Storm-Blue Slim-Fit Peached Stretch-Cotton Blazer

  • Valentino Valentino Garavani Open Striped Leather Sneakers

Brands to look out for:
Officine Generale, Valentino, Tomas Maier  

Your signature fragrance:
Mister Marvelous Eau De Parfum – Neroli, Green Lavender, 50ml, by Byredo

  • Alasdhair Willis and Stella McCartney, New York, May 2015 Raymond Hall/ Getty Images

According to cultural cliché, your forties is supposed to be the point at which you’re veering into “mid-life crisis” territory. But this insidious myth (only sometimes true) shouldn’t stop you from exercising a bit of flair when it comes to getting dressed. In this phase of your life, tailoring makes a reliable bedrock for every outfit, a well-cut jacket being both flattering to the figure and age-appropriate. But that doesn’t mean you have to look like a banker all the time. Instead, invest in contrasting separates, like Mr Alasdhair Willis, above, who retains a subtle edge of style in this look with sand-coloured chinos and a navy double-breasted blazer. Avoid fustiness by wearing a T-shirt instead of a shirt and, in summer, try going sockless, or contrasting your smart-casual look with a pair of white Converse sneakers. For more formal events a sharp, slim-cut, single-breasted suit from Italian experts Canali, worn with a pair of round-toed “Shannon” shoes from Church’s, will ensure “cool dad” status.

What to Wear

  • Caruso Blue Butterfly Slim-Fit Double-Breasted Wool-Hopsack Blazer

  • Incotex Four Season Relaxed-Fit Cotton-Blend Chinos

  • Stefano Tonchi, Perez Art Museum, Miami, December 2013 Neil Rasmus/ BFAnyc.com

Congratulations on making it this far! As a reward for your efforts (we’ll assume), you’re now the boss, family patriarch or – if you’re a more freewheeling artistic sort – at the height of your creative powers. You can therefore dress the “older, wiser” part with real authenticity, and for this purpose there are few things better than a double-breasted suit, as modelled by W Magazine’s editor-in-chief Mr Stefano Tonchi, above. In former times, this was a cut reserved for royals and tycoons but thanks to recent, slimmer offerings from the likes of Kingsman, Kilgour and Gieves & Hawkes it can now also have a lighter touch and work throughout the year. Opting for a variation in a classic English pattern such as Prince of Wales Check or herringbone will, at your fine age, look venerable rather than stuffy, so don’t be afraid of experimenting, texture-wise.

What to Wear

  • Kingsman Harry's Navy Super 120s Wool and Cashmere-Blend Suit

  • TOM FORD Button-Down Collar Cotton-Blend Twill Shirt

Brands to look out for:
Kingsman, CharvetBerluti

Your signature fragrance:
Brioni Eau de Toilette, 75ml, by Brioni


  • Bill Nighy, New York, March 2015 Alo Ceballos/ Getty Images

Freed (or soon to be) from the shackles of work, you are now a man of your own devices, beholden to no one – a fact that can be reflected in your choice of clothing. Tailoring remains a flattering option, but will work best if you allow a little looseness in the wearing of it. The pleasingly louche Mr Bill Nighy always provides good guidance on this front, often forgoing a tie – above, he wears a scarf tied in a relaxed knot instead – and opting for a long, straight-cut coat for a more romantic silhouette. Strong and dark colours work best with grey hair so, if you do add denim (in the form of a shirt or jeans), make sure it’s in deep, unwashed indigo.

What to Wear

  • Ermenegildo Zegna Mélange Alpaca-Blend Overcoat

  • Loro Piana Duo Fringed Cashmere and Silk-Blend Scarf