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The Knowledge

A Modern Dad’s Guide To Dressing His Son

The clothes your child should be wearing this summer – and how to get them into the damn things

Children: you’ve no doubt seen them on your social media feed (perhaps a little more than you’d like). Maybe you’ve even encountered one in person. And sooner or later you might have one of your own – if so, you are going to have to learn how to dress them.

Now, we assume you know how to dress yourself – you’re here on MR PORTER, after all. But the rules that govern your wardrobe work in mysterious ways when scaled down. For starters, gender conventions can prove difficult to swerve: girls often seem to come pre-programmed to adhere to that Frozen princess aesthetic, while for many boys, what they want to wear is merely something that either aids – or at the very least doesn’t impinge on – them destroying everything in a room. With your son particularly, you’ll find it hard not to subconsciously imprint ideas of masculinity onto their style of clothing. “You bring your own sense of what a boy should wear from the dark recesses of your own pathetic caveman mind,” says Mr Alex Bilmes, editor-in-chief of Esquire UK, Style Council Member and father of two, one of each.

To improve the way we dress our children, we sought advice from some style-minded dads. We asked them how the codes of men’s clothing work for young boys, if investment pieces are worthwhile when the wearer will have grown out of them by the following month, and how in the name of all-that-is-holy are you supposed to get poppers to align.

Here then, is everything you need to know about dressing your little man.  

He is his own man (or boy)

When it comes to dressing another male human, the obvious solution is to draw on your knowledge of dressing yourself. But that doesn’t mean you should dress your son exactly like you.

“The ‘mini-me’ look works well for leaders of totalitarian regimes and their children,” says Mr John Brodie, SVP of brand marketing and content at J.Crew (and formerly of this parish). “But for the rest of us, a smarter way to go is to have certain connective element in the way a parent and child dress but stop short of a full replica.

“I like it when I see a floral pattern on a daughter’s dress echoed in the silk of her father’s necktie or a father and son both wearing the same suit, yet while the father wears it with a dress shirt, necktie and brogues, the son wears it with a T-shirt and box-fresh sneakers.”

Something that should also be avoided is what we shall call “Prince George syndrome”; as Mr Bilmes puts it, “the kid with the shirt and tie and the brass-button blazer” – sure, you might think the outfit is cute, but that doesn’t mean your son will. “He just seems all awkward and shy,” Mr Bilmes adds.

The key here is to take what you know, but add what you know boys get up to. “I do dress him like me,” Mr Olie Arnold, Style Director at MR PORTER, says of his four-year-old son. “He has slim jeanshoodies and a MA-1 bomber jacket. But he loves jumping, climbing and playing – and we buy him clothes to suit that. More often than not, he’ll run to the park, take his sweater off, throw it on the floor and leap on it.”

“The father is the classical score and the son should be the slightly mad jazz improvisation,” adds Mr Brodie. The rules are something to play with.

Daddy cool

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Never forget: he is Batman

Mr Matt Coyne is the author of the blog Man Vs Baby and the fatherhood manual Dummy: The Comedy And Chaos Of Real-Life Parenting. He says that you can tell at a glance whether he or his partner dressed his son that morning: if his partner dressed him, his son will look “preppy and smart”; “if I’ve dressed him, he will be dressed as Batman”.

When it comes to clothes for boys, superheroes have become hard to avoid – not that you should necessarily want to. For Mr Coyne, a comic-book fan himself, these super-powered alter egos provide part of his family’s identity. “We’re defining them [the children] as an important member of our tribe and I think that’s a positive thing, rather than something to be discouraged and made to feel a dick about,” Mr Coyne says. “But maybe we also dress our children in things we can’t get away with wearing ourselves.”

Nearly everything Mr Bilmes’ son wears also has a comic-book character plastered over it, and he is cool with that. “When you get to be as boring and old as me, you never wear anything that isn’t navy or grey or at a push a white T-shirt – that’s as adventurous as I get,” he says. “One day, he’ll be like me. I hope not, but like most British men, he’ll probably end up wearing navy blue. I think it’s fantastic he gets his years when he wears yellow or red, Avengers and football tops.”

In fact, the brighter the clothes, the better. Mr Olie Arnold says his son’s bright orange jacket makes him easier to spot in a crowded park. “As soon as your boy starts running about, you’ll turn your back for a second and he will be gone. Your heart goes because you think you’ve lost him – then you see that orange coat.”

So, the Dark Knight is good, but the orange Power Ranger is even better.

Daddy cool

  • Neil Barrett Printed Cotton-Jersey T-Shirt

  • Converse 1970s Chuck Taylor All Star Canvas High-Top Sneakers



Buy smart (and never turn down a hand-me-down)

You won’t be surprised to learn that we at MR PORTER live by the maxim “you get what you pay for”: better-quality clothing might come at a price, but it tends to last longer. But what if an item was unlikely to fit the wearer by next week?

Once on a work trip to Los Angeles, Mr Arnold brought back a Kenzo jumper for his son. “He’d had a growth spurt while I was away,” he says. “I put it on him and it was tight. He maybe wore it twice – I’ve got one picture of him in it.”

Mr Brodie suggests that expensive items should be considered on a case-by-case basis. “Maybe not a Givenchy rottweiler T-shirt,” he says. “But one Christmas, I gave our son a Hackett tweed blazer. I bought it a size too large and he got three seasons out of it.”

“It does pay to go for good-quality clothing that washes better,” says Mr Arnold, pointing out that you will be washing it a lot. “We bought this really nice striped top from COS for our son when he was two. He’s now four and he still wears it. It’s grown with him, weirdly. When you find a brand that works, stick to it.”

But there’s no indignity in hand-me-downs, depending on who you ask. “I’m not precious,” says Mr Bilmes. “We’ve got lots of well-to-do friends with children a little bit older than ours. I’d say about 80 per cent of our son’s stuff has been given to him and he doesn’t make a fuss – or doesn’t know. He might get angry when he finds out.”

(Don’t tell him where his Hulk costume came from, then.)

Daddy cool

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Their bedroom is a battleground

When it comes to physically dressing your child, the first step is to understand who you are dealing with. “A baby can fight being dressed like a cornered, syphilitic badger,” says Mr Coyne. “Sun Tzu once wrote [in The Art Of War]: ‘Know your enemy and you can fight a hundred battles without disaster.’ So studying your own baby’s strategies for avoiding being dressed is absolutely vital.”

Like a Terminator, very young children – or older ones in an apoplectic meltdown – cannot be reasoned with, but later, a combination of bribery, distraction and threats can hold some sway.

“You just tell them that nothing is going to happen today until they put their clothes on,” Mr Bilmes says. “I resort to bribery every minute of every day. I don’t think there’s any shame in it – what else are you going to do?”

There are however easy wins that can help you take a bloodless victory. “You’ve got to have something you can get them in so you can get them out of the door quickly,” says Mr Arnold. “Velcro instead of lacessweatpants – poppers should be avoided as much as possible.”

Poppers or press studs are something you are bound to form an opinion on, and that opinion will mostly likely incorporate swear words. “These simple little inventions are a great idea when there are just a couple of them on a vest,” Mr Coyne says. “But on some garments they are everywhere, thousands of the pissy things. All of which need to be lined up correctly…”

Mr Coyne has a better idea: “If we can make instantly removable, Velcro trousers for male exotic dancers, why can’t we do the same for our babies?”

Daddy cool

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  • Battenwear Active Lazy Linen and Cotton-Blend Shorts



Don’t lose sight of your own style

Whether through the weight of responsibility or sleep deprivation, you might find parenthood impacts on your own wardrobe – even if it is just damage limitation. “I wear a lot more dark clothes,” says Mr Arnold. “Things where you can easily hide stains. I’m a lot better with dirt than I used to be.”

But when in public, there is no excuse to let standards slip, warns Mr Bilmes. “Just because you’ve had a kid doesn’t mean your life is over and you have to turn into a slob who wears tracksuit trousers with bits of pizza stuck to them,” he says.

Then again, don’t go too far in the other direction, believing now you have a child you should dress to impress them – they won’t be. “There are men who maybe dress to make their kids think that they are cool,” Mr Bilmes adds. “Nobody’s kid ever thinks they are cool – it is a waste of time. But that isn’t to say don’t make the effort.”

If – and that’s a big if – you do get some acknowledgement of the lengths you go to just to put some clothes on, embrace it. “If I come home and I’m wearing something a bit fancy, my son might say, ‘Daddy, you look cool today,’” says Mr Arnold. “I know he has no frame of reference, but I’m going to take that.”

And that might be the best compliment you get all year.       

Daddy cool

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Support Father And Son Day

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  • Orlebar Brown Father & Son Printed Cotton-Jersey T-Shirt

  • Orlebar Brown Father & Son Printed Cotton-Jersey T-Shirt