John Fitzgerald Kennedy will forever secure a place in the legend of the United States as much as he does in its history. The fresh-faced 35th president and scion of the closest thing this country has ever had to a royal family still represents to many the promise of an American optimism, long after being gunned down in what is arguably the most conspiracy-riddled event in our history. He was also the youngest elected president and, with his tousled sandy hair, toothy smile, rugged good looks, easy charm, and calm visage, has come to embody the ideal of classic American style.
Kennedy’s ease of being and comfortable, casual fashion sense left a mark not just on American menswear, but the very office of the president. By being less than formal, he let the public in, made them feel comfortable with him as a human being as well as a world leader. It’s a move still employed today, every time President Obama releases a playlist or frolics in the surf.
As summer winds down, Kennedy’s casual style is a perfect way to beat the day’s heat and segue into cooler evening temps. Think classic New England prep, or, more specifically, preppie’s grown-up version that was once famously known as “Ivy League,” but with a bit of sun bleaching and sand wear at the edges. Comfortable, easy, but classy at the core.
And remember, just because you’re laid back doesn’t mean you have to be complacent.
JFK was hardly ever seen in the sun without his shades, and he knew how to wear them in such a way that they were casual without being too casual. Ray Ban’s Wayfarer Tortoise are pretty much a match, but if you really want to emulate those JFK vibes, then get the exact same model he wore back in the day at a vintage shop.
THE OXFORD SHIRT
So named because of its thread weave, the Oxford shirt is a stylish man’s best friend. From its origins on the rugby pitch, it’s worked its way into an Ivy League staple. Soft enough to be comfortable anywhere, it’s one of a very few dress items that gains character with age and washing. On top of that, it goes with everything. Shorts, jeans, khakis, under a blazer, or over your lady friend, it’s versatile enough to be thrown on for whatever occasion arises. Ralph Lauren makes a modern classic, and Saturdays’ Crosby Oxford is an updated home run of a staple shirt.
No, not the pleated, baggy-thighed behemoths those old men at the auto parts store wear too low for everyone’s comfort level. Straight or slim cut, a little stretch is OK. Forget the pleats, unless you happen to be pairing with a tweed coat and teaching an English lit class. Try tucking your shirt in, but still keeping it chill with a woven belt, and get them taken up—don’t peg them. Bill’s Khakis makes a killer pair right here in the U.S., and if you need them now, your local Banana Republic has some good options as well. Remember, lighter tan in summer, darker as the seasons go on. And don’t be shy about a crease.
…WITH A BLUE BLAZER
Whether you’re partying on your sailboat, chilling by the fire at the beach house, or headed in to a couple meetings before taking off for the weekend, a proper blue blazer paired with khakis will make sure you look up to speed without going off the rails. It’s a look Vineyard Vines has based its whole line around, and one that Brooks Brothers has mastered. Too hot in the sun? Throw it over your shoulder and instantly channel the cover of GQ.
A WHITE T-SHIRT
If you must dress down, do it with a plain white t-shirt. And if you’re going basic, don’t overdo it. All cotton, ring spun soft, the chest pocket is up to you—but definitely don’t put anything in it if you opt for one. Calvin Klein has you covered, but if you want to go above and beyond, try the Welcome Stranger 8 oz Bison tee. You should have one of these on at all times, under that oxford shirt.
PINSTRIPE SUIT, TAILORED
Unlike the frumpy boxes of polyester most politician marinate in, JFK knew that it was important to dress to impress. So when it was go time, he ditched the beachfront casual and slipped into a well-tailored suit, either dark and solid or, from time to time, with a subtle pinstriping. Indochino has an affordable wool option, and JFK himself was famously a Brooks Brothers fan. But if you really want to go for it—and every man should, at least once in his life—get fitted for an Armani, who’s Trader Line Suit would make Jackie O beam with approval. Remember, fit is everything here: no bagginess, no slouching. The pinstripe suit, when worn correctly, is straight gangster, but to do it wrong is just criminal. Don’t forget the pocket square.
AND A SKINNY TIE
There are almost as many bad ties in the world as there are ties. Why is it so hard to get a good one? Who knows. But Kennedy knew that having the perfect tie tied together an already impressive suit which, wielded properly, would help him command a room’s attention without saying a single word. No excessive bottom flare, and with a simple pattern and you’ll be doing fine. J Crew’s Italian silk repp tie is a great choice, or the Brooks Brothers’ BB#4 slim. If you’re feeling extra cocky, show it by going with a bow tie, worn maybe just a little askew. Oh, and no clip-ons, of course—this isn’t the Cub Scouts.
It gets cold at the end of those New England days, and Kennedy knew that the key to stylishly beating the weather is a wool knit sweater. Orvis’s Black Sheep fisherman’s sweater will keep you cozy yet cool in the crispest of evenings, or, if you prefer something a tad less itchy and durable but way softer, Ralph Lauren’s cable knit cashmere will do the trick.
Unless you’re fronting a rock band, you don’t need a lot of accessories. One thing every man needs, however, is a good watch. Understated, tough, and definitely not digital are good rules to live by when shopping for a permanent timepiece. JFK wore an thin, rectangular Omega watch for much of his presidency. If you don’t want to drop several weeks’, or months’, paychecks on a wristwatch, well, we hear you. This is one item, however, where a man deserves to treat himself a little. Will the Timex you copped at the mall work just as well as the Swiss timepiece you saved for? For the most part, yes. But will it add a little swagger to your step? Probably not. To save a little cash, check out Huckberry’s rotating collection of vintage Rolexes, or stay presidentially nostalgic and head to Omega’s own vintage shop.
You can’t always wear dress shoes or boat shoes. Sometimes you have to get sporty, even if you’re wearing a blazer. Yes, JFK rocked sneakers with his suits from time to time. Nothing wrong with it. Stick to a classic profile, like the Converse Chuck Taylor All Star or Tretorn Nylites that Jack himself favored.
Actually, there is no hat. Kennedy’s lack of love for hats has been credited by many with killing the then-booming men’s headwear industry. At the time of his inauguration, you’d have been hard pressed to find a bare man’s head on a busy city street. Soon after JFK started appearing bareheaded daily on television and the front pages of the nation’s newspapers, the men of America soon followed his lead. Coincidence? The internet rumor-debunking site Snopes rules JFK’s assassination of the hat trend as a falsehood, but there has been enough research done by reputable outlets to make the issue worthy of argument. Either way, when was the last time you saw someone wearing a fedora or top hat to the office?