How to dress like the man who mastered relaxed confidence and laid-back sophistication:
1. Invest in a statement watch.
Once 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.
3. Master the mismatched suit.
4. The white oxford is beach uniform.
5. It’s okay to dress down an outfit with sneakers.
6. Crease your pants.
7. Always have a wool sportcoat on hand.
Because every gentleman knows that black tie means black bow tie.
8. Know the right pair of sunglasses for your face.
9. 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.
10. The oversized sweater is your friend.
11. 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.
12. A plain white t-shirt can look put together.
13. A skinny tie with a simple pattern never fails.