How to Dress Like John F. Kennedy

jfk wearing a blue polo shirt and white chinos on a boat
How to Dress like John F. Kennedy - PHOTO CREDIT: Pinterest

John F. Kennedy was one of the most stylish presidents that ever stood in office, and here at The Idle Man we think that you could all learn a little from the man himself.

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When it comes to wanting to model yourself on someone who had unwavering amounts of sophistication, an understated style and a discreet arrogance, then JFK is your man. Always well presented, always in-line with fashions and always low key but powerful in his appearance, he continues to be a style icon for many.

To start with, you need to look at JFK’s wardrobe as a whole and not just the one that was in-keeping with his presidential duties. Kennedy would always achieve his confident and relaxed style in all areas of his life, from work commitments to family holidays, and we’ve collaborated a list of top styles that Kennedy fashioned.

Mis-matching Your Suit

For the less formal of occasions, Kennedy would often team a pair of trousers with a different coloured jacket, giving him a more down to earth style for everyday duties. Something like a pair of light chinos or trousers with a darker jacket is ideal, and great for smart-casual and work events.

Try wearing this grey tweed blazer from The Idle Man, a classic piece to own in your wardrobe arsenal. Slim fitting and classically cut, it will make the perfect accompaniment to these straight legged chinos. Team these with a classic boat shoe to top off the look, or, maybe even a loafer.

jfk mis matching trousers and jacket
SHOP: The Idle Man Tweed Blazer | Dickies Slim Straight Work Pant

Keeping it Cool on the Beach

On family holidays, JFK wouldn’t always be pictured chilling out on the beach in a white t-shirt. Instead, to keep his dapper look alive, he chose a white oxford or linen shirt to do the trick. Giving him a sophisticated edge and one that doesn’t look out of place with some tailored shorts; this is the ideal getup when you’re wanting to look a little smarter on holiday.

Try wearing a crisp, classic white button down shirt. This one from yours truly, The Idle Man, is spot on for creating a summer casual look. Teamed with a pair of twill shorts from ourselves as well to heighten the look and keep it casual.

jfk white shirt and shorts outfit grid
SHOP: The Idle Man Smart Shirt White | The Idle Man Twill Shorts Grey

Don’t be Afraid of Trainers

When he was out and about John F. Kennedy wasn’t afraid to wear some smart chinos with a pair of retro trainers, and a simple shirt and jumper. It offered an understated and casual style but without him losing any of his sophistication.

You may not own a yacht, but your footwear can certainly make people think otherwise. JFK was often spotted manning his boats in a pair of white plimsolls, for grip and comfort I should think. So, why not try emulating this by wearing this pair of white plimsolls from Vans, perfect for those casual days out, or, maybe even manning a boat of your own.

jfk white trainers outfit grid
SHOP: Vans Authentic Plimsolls White | Superga 2750 Cotu Classic Plimsolls White

Know How to Rock Sunglasses

Another iconic accessory that you’d often see JFK wearing was his sunglasses. Always suited to his face, these accessories added to his refined appearance and they are also great for making you look confident when you might not necessarily feel it!

Sunglasses are the perfect way to heighten any look, formal or casual, and no man did it better than JFK himself. Try wearing a pair of classic Ray-Ban‘s in black, the perfect pair of sunnies for any man. Or, if you’re after something a little bit different then why not try wearing a pair in tortoiseshell. This pair from Persol are spot on

jfk sunglasses outfit grid
SHOP: Ray-Ban Wayfarer Leather Sunglasses with Polarised Lenses | Persol Folding Crystal Lense Sunglasses PO0714 | Ray-Ban Clubmaster Sunglasses

Bow Ties

When you do have to attend a formal event, don’t be afraid of the bow tie. It’s a classic winner and really adds to that air of self-assurance that you’ll need to adopt to get across the true character of JFK.

the idle man black bow tie
SHOP: The Idle Man Bow Tie Black

The Long Overcoat

Finally, if you want a piece of clothing that’s going to make you look important no matter what it is you’re doing, then you need to invest in the long overcoat. Paired with an outfit of your choice (as long as it’s not your pyjamas or slacks) it instantly provides that confident edge to your outfit.

And, if you opt for a black one, you’ll know it’ll go with almost any outfit and is the true classic colour, making it ideal for work and social. This one from Selected is spot on, classically designed so it hugs your body and you know it will go with pretty much anything and everything in your wardrobe.

jfk black coat outfit grid
SHOP: Religion Blanc Crombie Coat Black | Selected Brook Coat Black

And On That Note

To achieve the look and style of JFK, you’re going to need to make sure your wardrobe oozes sophistication and that you bring confidence to the clothes you’re wearing. Pick out the sharp shirts, the tailored trousers and the designer sunglasses and put on your ‘I’m serious but still fun’ face and you’re bound to rock John F. Kennedy’s style, and rock it well.

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