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How to dress in your 40s

Words by Rob Chilton

After years of style mistakes and wrong turns, here’s what I’ve learnt about what to wear when you hit your 40s, by EDGAR editor Rob Chilton (age 43)

Find a uniform

I do not look good in hoodies. I do not look good in baggy clothes. I do not look good in hats. I’ve never tried on any items of luxury athleisure wear but I’m 99 per cent sure I won’t look good in those either.

My 40s have been the time that I decided to stop experimenting and stick to what I know works. Life is too busy to put together a complex outfit every morning so I rotate around a few set looks or uniforms that I know suit my body shape and, more importantly, make me feel good.

For example, a t-shirt under a denim shirt; shirts with a grandad collar; dark chinos, not jeans; simple white trainers or brown boots. Nothing is baggy, everything is slim fit. No cheap shiny polyester, just good cotton or wool.

Tom Hardy

Keep it simple

There are certain things a man in his 40s should not do: behave badly in public, use foul language, dance for more than two songs consecutively. He should also not try to dress like a man half his age.

Therefore, any wild graphics on clothes probably aren’t going to work for you. Similarly, any items of clothing with prominent brand names splashed across the front, philosophical messages or ‘amusing’ phrases should be binned immediately. Understated clothing is sophisticated, smart and cool for a fella past 40.

John Legend wears Hugo Boss

Look after your clothes

Iron shirts, polish shoes, get things dry cleaned, hang clothes on a hangar, get things altered if they’re not quite right, don’t go to work wearing a shirt with toothpaste on it. We’re over 40, my friend, so let’s smarten up and dress our age.

Stick to colours that work for you

I recently threw a shirt in the charity dumpster. It was from Paul Smith and I bought it because it had a cool print of small bicycles on it, which I loved. The problem is that the shirt was a sort of pale pink colour. I wasn’t sure if it suited my skin tone when I tried it on, but I persisted because of the bikes. Bad decision.

I stubbornly wore it a few times, knowing that it made me look ill and washed out, and I never felt good in it. Choosing colour is all about instinct: go with what makes you feel confident. For me that’s white, all shades of blue, burgundy and green. Yellow, black, beige, grey, red and the dreaded pale pink? I don’t go near them.

Matthew McConaughey in Dunhill

Brand loyalty

My scattergun approach to buying clothes in my 20s and 30s meant I had a wardrobe filled with the A-Z of brands. But as the years have passed I’ve whittled down that list to just a few trusted labels that I know fit my body and whose style philosophy meshes with mine.

Paul Smith is great for suits and shirts with a twist of fun; Copenhagen brand NN07 makes chinos that are perfect for my stupidly long legs; Ralph Lauren t-shirts and shorts hit the spot; Orlebar Brown swim shorts are worth the money, as are Moscot spectacles; Grenson shoes in a size 12 feel like they were made bespoke for me.

And I won’t leave the house without wearing Tommy Hilfiger boxer shorts. In an ever-changing world, loyalty means something.

Moscot eyewear

IWC Portugieser Yacht Club Chronograph

Buy a nice watch

I got married at the age of 40 and decided it was time to mark both these milestones by investing in a proper watch. After much research online and in-store I opted for a Bremont pilot watch.

It’s the most expensive thing I’ve ever bought and I don’t regret it for one minute. I wear it every day, I still love it and I know I will have it to my dying day. The memories that are attached to it – my wedding day specifically, not turning 40 – make me smile.

Quality, not quantity

There was a time in my early 30s when my wardrobe was stuffed with clothes that I didn’t wear. Opening the doors every morning was overwhelming as I was blinded by a mish-mash of fabrics, colours and cuts.

I owned six pairs of jeans, which is ridiculous – nobody needs six pairs of jeans. I slowly realised that it was time to stop buying from the high street and step up to the next level of menswear store.

Now, my style rule says that, rather than buy three cheap white t-shirts, it makes much more sense to pool that money and buy one fantastic white t-shirt that fits well and has lasting power.

EDGAR editor, Rob Chilton

Comfort is king

For years I would squeeze my feet into shoes that I love – but were too small for me.

I felt guilty about letting them rot in the back of my wardrobe and therefore, every few days I would sigh, reach for the leather torture devices and cram my protesting feet inside, even though I knew that by lunchtime my feet would be red raw and throbbing. Don’t sacrifice pain for style.

Shoes (and clothes) should fit you properly and make you feel confident – nobody enjoys blisters and bunions or a waistband that cuts you in half.

Justin Theroux in Louis Vuitton

Wear it with confidence

The best fashion accessory is not a Tom Ford belt, a pair of Dunhill cufflinks or an IWC Portugieser (although those things would be rather welcome in my wardrobe). No, the best way to finish off an outfit cannot be bought in any store: it’s attitude. So walk tall, put your shoulders back, and smile.

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