Fashion
14 Style Lessons I Learned From JFK
How to dress like the man who mastered relaxed confidence and laid-back sophistication.
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1. Invest in a statement watch.



Once you find a watch you love, you'll feel naked without it. It doesn't necessarily have to be a luxury watch—the simpler, the better when it comes to everyday wear. My go-to watch has a simple gold rectangular case with a dark brown alligator strap.


2. When in doubt, throw on a chunky crew-neck sweater.



A great crew-neck sweater, preferably in neutral tones like oatmeal or camel, is the epitome of casual chic.


3. Master the mismatched suit.



For less formal events and dinners, pair a darker wool or tweed jacket with a crisp pair of lighter slacks. It says, 'I know how to dress, but I don't take myself too seriously.'


4. The white oxford is beach uniform.



Whether on the Atlantic or Pacific, Mediterranean or Baltic, opt for a white oxford or linen button-down rather than a graphic tee or tank top.


5. It's okay to dress down an outfit with sneakers.



I love to dress down an everyday put-together look with a pair of simple sneakers, like these classic Vans from J. Crew.


6. Crease your pants.



Before any event, make sure your pants are creased and your shirts are ironed, preferably at a dry cleaner. People will notice.


7. Always have a wool sports coat on hand.



JFK mastered the Ivy League look. Elevate any outfit with a tailored wool sportcoat.


8. Wear a bow tie every chance you get.



Because every gentleman knows that black tie means black bow tie.


9. Know the right pair of sunglasses for your face.



Invest in the perfect pair of sunglasses, and wear them confidently.

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10. A long overcoat is the best kind of overcoat.



It's time to say adieu to that cropped peacoat you've rocked since you were eight years old. A long wool or cashmere overcoat says, "I'm on my way to a very important meeting"—no matter where you're heading.


11. The oversized sweater is your friend.



Sunday morning? Oversized sweater. Long flight? Oversized sweater. Running late to work? Oversized sweater.


12. The right frames can change your face in a good way.



A friend of mine once told me I look better when I'm wearing my glasses. I didn't know if I should be offended or not; JFK was rarely seen in his round tortoiseshell frames. Either way, the right pair of glasses—for those of us who aren't 20/20 fortunate—can embellish an already-handsome visage.


13. A plain white t-shirt can look put together.



A well-cut tee, like this one from Incotex, coupled with a pair of black jeans or navy chinos, evokes an understated sophistication.


14. A skinny tie with a simple pattern never fails.



A simply patterned necktie adds a fun twist to any plain grey or navy suit.

*This story originally appeared on Townandcountrymag.com
*Minor edits have been made by the Townandcountry.ph editors

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Tucker Westbrook
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