1. Invest in a statement watch.

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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.

JOHN F. KENNEDY PRESIDENTIAL LIBRARY AND MUSEUM

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



3. Master the mismatched suit.

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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.

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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.

JOHN F. KENNEDY PRESIDENTIAL LIBRARY AND MUSEUM

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.

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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 sport coat on hand.

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

8. Wear a bow tie every chance you get.

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

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

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

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

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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.

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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.

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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.

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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.

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

Tucker Westbrook A lot of town and a little bit of country.

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