How to dress well in your 40s and 50s: ditch the converse, get a good coat, be careful of roll-necks

Don’t dress for your age; the beauty of ageing is having the confidence to be yourself

Quentin Fottrell in a striking pair of shades.

Quentin Fottrell in a striking pair of shades.

 

My friend Jimmy Kaston is full of wonder. Here are a few words that sum him up. Authentic. Fanciful. Funny. Serious. Colourful. Monochrome. Surprising. Audacious. Inspirational. Classic. Outrageous. Inappropriate. Appropriate. Glamorous. Militaristic. And that, my friends, is just his wardrobe. Shirts and bow ties and waistcoats and cravats are not just clothes for Jimmy. They’re a reminder that you should always be who you are, and not what others expect you to be.

Jimmy works in the antiques business and lives in New York. He is just north of 60 and ageless, at the same time. His wardrobe changes with his mood. One day, you might meet Disco Jimmy. The next, Golden Age of Hollywood Jimmy. He could show up in a white linen suit, a seersucker sports jacket, a long skirt or kilt or a smart leather harness over his shirt. On our last thrift-shopping excursion in the East Village, I bought a “crapulous” gold sparkly jumper for 10 bucks and an orange jacket by Fendi.

“What do you think, Jimmy?” I’ll ask him. Jimmy usually stands back, gives my deliciously ludicrous choice a once-over with a glint in his eye. Then, he answers. My style has evolved as I have matured, but my sense of fun is unchanged. My life and, ergo, my wardrobe sparks joy. I wore a white lace shirt when I was three. Today, I own a Vivienne Westwood rugby shirt, also with a lace collar. “They want us to be invisible,” Jimmy said on our last outrageous excursion. “But we’re not the type.”

He’s not wrong. When you get older, society very slowly and rudely starts to peer over your shoulder. Corporations are obsessed with men and women in their 20s and 30s. If you are in your 40s, 50s, 60s or beyond, the advertising industry does not have the time or money to spend on you, unless it’s selling you prescription medication. So I was perplexed, befuddled and bewildered to read a recent article in The Guardian entitled, “What not to wear if you are a man over 50.” I had one thought: ‘Wow.’

Age appropriate

Fashion editor Adrian Clark recently turned 50, and decided to assess the “age appropriateness” of his wardrobe. “You are forced to make decisions on what you should not, as opposed to should, be wearing,” he wrote. “A lot of men entering their 50s fall into one of two camps (with a minority bridging the divide): those who have given up, and those who don’t know when to give it up.” He regards Converse sneakers as a sign of someone who is “desperately trying to hang onto their youth”.

Ger Philpott, a Dublin-based producer, says he avoids advice on what to wear.
Ger Philpott, a Dublin-based producer, says he avoids advice on what to wear.

Hang onto what, now? Youth is a gift and ageing is something you earn, with a little bit of luck. Here are some of the things I love about being in my 40s: I can dance for hours without the need to have a drink; I endeavour to tell people exactly how I feel in the moment; I happily leave parties before the clock strikes 10; I write “XXX” to my straight male friends; and, if I were to date a man who wanted me to tone down my wardrobe, I would clink my silver cufflinks together three times, and make him disappear.

I asked some men who are all 50-plus what they think of the idea that middle-aged men should start editing what we wear. Women, of course, have been dealing with this brand of sartorial ageism (and sexism) for millennia. Seems only fair it’s our turn to deal with it, and fight back.

“You are never too old to wear a good leather jacket,” says filmmaker Conor Horgan. “As one heads into one’s 50s, it becomes increasingly important to only wear whatever the hell you want, whenever the hell you want to.”

Chef Kevin Thornton has never felt the need to keep up with trends or be restricted by what is considered appropriate for a man who is 50 or, in his case, 60. “Contriving to give off a certain vibe and feeling forced to act in a certain manner all sound like unhealthy states of mind to me,” he says. “I don’t know how I would describe my style. My 25-year-old son and I share a lot of clothes, which I guess isn’t something that’s too common.” He won’t volunteer this, so I will: Thornton is in great shape.

Chef Kevin Thornton has never felt the need to keep up with trends or be restricted by what is considered appropriate for a man who is 50 or, in his case, 60.
Chef Kevin Thornton has never felt the need to keep up with trends or be restricted by what is considered appropriate for a man who is 50 or, in his case, 60.

Since his late 30s, Irish fashion designer Peter O’Brien has stuck to a uniform of navy suits, navy or black knit polo shirts or V-necks, and Church’s Shannon shoes in black or dark brown. “Add a few Victorian diamond pins and that is it,” he says.

“Folk should wear what makes them happy regardless of age, and being over 50 is no reason to own only porridge-coloured shapeless garments. I certainly don’t. What I wear is absolutely informed by my taste and not the date on my birth certificate.”

Body shape

Some men do believe that you do need to be cognisant that your changing body shape informs your clothing choices when you get older. “Roll necks make a 50-year-old look 70 unless they are built like a Helmut Lang mannequin,” says Peter Westcott, a London-based textile designer and property developer. “The same goes for chinos on a flat arse. Knitwear is beautiful, but slightly oversized hoodies hide the gut better and the hood disguises the shortening neck and the beginnings of a stoop.

“I tend to buy sales clothes because if you look too up-to-the-minute you can look desperate,” he adds. “My favourite look is a dark hoody, stretch jeans and Hunter gum boots and some oversized jacket or coat. I’m a hot mess at 60. But I don’t give a toss. If I had the body shape I yearn for, I’d dress differently. But that’s not going to happen. Personally, I never ever wear black shoes or boots. I can’t even walk in them. They are like little hooves or trotters. Dark brown is fine.”

Ger Philpott, a Dublin-based producer, lives in a Ralph Lauren navy pea coat and says he avoids advice on what to wear. That doesn’t mean he doesn’t have opinions on what looks good or not. Some might argue that cargo pants or tracksuits don’t look good on any man, regardless of age. But Philpott says he would never tell someone not to wear something solely because of his age. “The beauty of turning 50, and beyond, is having the confidence to be yourself,” he says. “This gives me joy and freedom.”

Joy and freedom, they are two rewards that should not be underestimated, and are more valuable than any compliment. “Our clothes demonstrate individuality, rebellion or just plain comfort,” says Christopher Shea, a New York-based psychotherapist.

“If certain threads please you, then go for it. It’s not just good fashion, but it’s also good for your mental health. Last year at 53, I bought a pair of camouflaged pants that I won’t give up because they feel great. I’m not hiding or fading into expected norms as I grow older.”

Middle-aged Quentin Fottrell rocking his beehive hat in New York.
Middle-aged Quentin Fottrell rocking his beehive hat in New York.

That’s why Adrian Clark’s wardrobe purge saddens me. Skinny jeans, parkas, baseball caps, Hawaiian shirts and fleece track-tops all make his ditch list. “Make friends with rollneck knits,” he writes. I’ll make friends with my Easter Bonnet, instead. It’s made of straw, and covered in netting and plastic bumble bees. It’s totally bonkers and I love it. If you think I look like I’m one bumble bee short of a hive, tough luck. I wear whatever makes me happy and, when I leave my 40s behind, I will continue to dress for me.

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