Scout Tips: JFK’s Fresh Code

esquire scout life jfk 01

How to dress like the man who mastered relaxed confidence and laid-back sophistication:

1. Invest in a statement watch.

esquire scout life jfk 02Once you find a watch you love, you’ll feel naked without it. It doesn’t have to be a Rolex or Jaeger-LeCoultre—the simpler, the better. 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.

esquire scout life jfk 03A great crew-neck sweater, preferably in neutral tones like oatmeal or camel, is the epitome of casual chic.

3. Master the mismatched suit.

esquire scout life jfk 04For 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.

esquire scout life jfk 05Whether 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.

esquire scout life jfk 06I 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.

esquire scout life jfk 07Before 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 sportcoat on hand.

esquire scout life jfk 08JFK mastered the Ivy League look. Elevate any outfit with a tailored wool sportcoat.

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

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

esquire scout life jfk 09Invest in the perfect pair of sunglasses, and wear them confidently.

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

esquire scout life jfk 10It’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.

10. The oversized sweater is your friend.

esquire scout life jfk 11Sunday morning? Oversized sweater. Long flight? Oversized sweater. Running late to work? Oversized sweater.

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

esquire scout life jfk 12A 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.

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

esquire scout life jfk 13A well-cut tee, like this one from Alexander Wang, coupled with a pair of black jeans or navy chinos, evokes an understated sophistication.

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

esquire scout life jfk 14A simply patterned necktie adds a fun twist to any plain grey or navy suit.

~Esquire

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