Even when you imagine Ted Kennedy in his last days, you still have the vision of him with his brothers.  Three handsome guys in the 60’s who had every opportunity in the world.  Three guys who went for it.

But when you look at the Kennedy style, you also notice something effortlessly classy about the gentlemen.  



None of them wears any item that appears to have been ironed that day.  There is no starch in those collars.  These are a group of boys who are going to run around to meetings and lunches, and maybe toss the football around the backyard after work.  

Bobby (middle) looks like he might skip out on his four o’clock and try to get out on the boat.  

Notice how John does something few men do today: he’s actually using his blazer pockets as pockets.  Mens’ suits always come with the pockets stitched up and Mens’ magazines always implore their readers to leave them stitched.  But you can imagine John scoffing at this advice (especially if it came from Bobby), saying – "Hey, it’s a pocket."

John was the leader of the pack after his brother Joseph died in the war.  And it is fitting that John Kennedy was the big brother for an entire generation of men.  John Kennedy showed up to meetings without a hat, and millions of men suddenly decided that their best head covering was a gift from god.

The Kennedys were also in a long line of people that liberated us from the overindulgence in dry cleaning.  Why suck the life out of a shirt and make it look like it should be hanging on a mannequin when you can wear a simple Brooks Brothers slim fit sport shirt?  You can wash it like you would a polo shirt, and then when it’s still damp you hang it up to dry and it ends up wrinkle-free. What you do with it after that is your own business.

Then again, there is a time and a place for everything:

A guide to the Kennedys in four parts:


The Big Brother.

Take a look at this glorious photo of our 35th president.  He’s the leader of the free world, and he’s also the captain of his own ship.  Note that the President skips two things: he doesn’t just dress like "one of the boys", and he doesn’t do himself the indignity of wearing a suit on his free time just to look more presidential.  It get windy out there so he’s keeping warm in the sun with a thin wool sweater and a smart looking pair of Ray Bans Wayfarers.

On a later, sunnier date, John entertains on the boat in a simple collared shirt.  The Wayfarers are with him for glare, but he still wants to enjoy the weather.  Notice how he gingerly keeps a hand on the wheel.  The Kennedys excel at making anything look easy.

Bobby Kennedy

The Gentleman with Dirt under his Fingernails (until right before supper).

Bobby Kennedy was known for getting his hands dirty.  Before his brother became President, Bobby squared off against Teamsters boss Jimmy Hoffa in a bold and daring series of senate meetings.  He also supported unfashionable things like civil rights.

Part of getting dirty is what made Bobby’s short life so worth living.  You can’t imagine Bobby Kennedy sweating over a ketchup stain on the sleeve of his shirt. As attorney general, Bobby kept two things in his desk: a spare shirt and a suit brush.  His father had a suit brush.  His brothers had a suit brush.  A little steam and a little suit brushing takes out anything worth worrying about.  Anything else is not worth worrying about.

The Kennedy grace and charm was strong with Bobby.  At a screening of a film after JFK’s assassination in 1964, Bobby waited for 22 minutes of applause to die down, and when he was asked to say a few words about his departed brother, he read from a passage given to him by Jackie O. from Romeo & Juliet.

and when [he] shall die

Take him and cut him out in little stars,

And he will make the face of heaven so fine

That all the world will be in love with night

And pay no worship to the garish sun.


The Elder Statesman.

In many ways, we have more to learn from Ted Kennedy than any of his brothers.  All of them inhabited their own myth.  Their youthful good looks were their introduction, and their charm their handshake.  Ted had a good run at this, but what we learn from him is how to grow old.

First, when you’re older, you make your own rules.  You’ve lived your life and you’ve done the best you could.  Now you can wear whatever blazer is most comfortable.  You can wear suspenders if you feel like it.

When you get older, you lose your looks but keep your character.  You may lose your eye for fashion but you keep your style.  And, like a robust vocabulary, as you age, you keep growing in grace.  Take this little bit from last year’s New York Times article about Ted:

When Mr. Kennedy learned that former Senator Tom Daschle’s brother was fighting the same type of brain cancer, the senator put him in touch with his doctors and opened his Boston home to him while he received treatment. He also offered assistance to the conservative columnist Robert D. Novak, a fierce critic of his, when Mr. Novak learned last year that he had a similar cancer.


The Matriarch.

But it wasn’t just the boys who had style.  Last month, Vanity Fair ran a cover story about Jackie O., whose influence on style can be seen even now in the work of designers like Christopher Kane, who emulates her grace and color pallette.  This article charmingly points out how Jackie was in a league all her own:

She spoke French to de Gaulle during Kennedy’s triumphant visit to Paris (“I am the man who accompanied Jacqueline Kennedy to Paris, and I have enjoyed it,” he famously remarked)

Now there’s a woman who knows how to make an impression.

She’s also a woman who knows how to grow into maturity and maintain her poise as a mother.  Here she is romping around with the kids with her hair down and a simple short sleeve knit turtleneck.

She held the country together when her husband was assassinated and stood by Vice President Johnson in her blood spattered Chanel suit as he was sworn in.

The only other public figure who has made such a gracious impression at such a young age is the current Queen of England.  If they printed Jackie O’s face on American currency, she would be depicted exactly as she was in Paris almost 40 years ago.