The fashion designer and budding hotelier may be the embodiment of American style, but his outlook is entirely global.

Tommy Hilfiger portrait
Credit: Susan Pittard

Uniform: When I travel, my navy blazer is my briefcase. I put everything in the pockets: my passport, wallet, cell phone, chargers, and business cards. I get custom suits made at Eredi Chiarini, in Florence.

Carry-on: My memoir, American Dreamer (Random House), comes out next March. Every time I flew, I would take a hundred pages or so with me to edit on the plane. It occupied a lot of time; I definitely didn’t sleep as much as I should have!

Art fix: I met Andy Warhol when I moved to New York in the late 1970s, and have always been attracted to his work. I have a deep understanding of it, because I was very entrenched in that pop-culture scene. My favorite piece is Grace Kelly; it reminds me of my wife, Dee.

Check-in: When the opportunity arose to buy the Raleigh hotel (doubles from $350) in Miami Beach, I jumped at it. The property is landmarked, so it still has this incredible charm. We plan to renovate and bring it back to its original state, which was so fantastic and unique.

Raleigh Hotel
Credit: Heather Smith Macisaac

Comfort food: Whenever I’m in L.A., I love to eat at Madeo Ristorante (310-859-4903; entrées $30–$45), which is a great old-school Italian eatery. There’s nothing better than pizza and pasta—real carb-heavy dishes—but I also like grilled branzino with a fresh salad.

Dream trip: Last year I traveled to New Delhi, where we marked a decade of the Tommy Hilfiger brand’s presence in India with a big event at the Leela Palace (doubles from $375). Everything in that country is so inspiring—the people, the food, the smells, the colors. I want to return to Jaipur and Bangalore.

The show goes on: To celebrate our 30th anniversary and our largest store opening in China, we re-created the Fall 2015 runway show from New York Fashion Week in Beijing. It took place in a full-size mocked-up stadium, complete with Astroturf, a scoreboard, and a Jumbotron. I think for an American designer to put on a spectacle like that really struck a chord with the Chinese. It was pure entertainment.