Maybe you'll be jetting off to Paris or Hong Kong on business, or to the lovely island of Mystique for pleasure. Really, if he wanted to, he could just sit in his superluxe apartment at The Plaza Hotel overlooking Central Park, arranging the dozens of upward facing pencils that sit on his desk in the library.
That's not the Hilfiger way, though. He likes to work. He wants to work.
He's been in the fashion business for more than 40 years, starting at a little denim shop in Elmira, N.Y., and now at the helm of a brand that's one of the most recognizable in the world. This spring, he added "American Idol" style adviser to his resume.
His peers at the Council of Fashion Designers of America honoured him Monday night with a lifetime achievement award.
However, Hilfiger, like previous winners Marc Jacobs last year and Michael Kors in 2010, says he feels a little young for it. "I remember when we were the young guys," he says of himself and fellow honorees. "I thought 'lifetime achievement' was for your 70s."
Yes, he's 61, he acknowledges, but there's a lot more to do. He ended his acceptance speech in front of a crowd that included Jessica Chastain and Kyra Sedgwick from Hollywood, and Anna Wintour and Donna Karan from the fashion world with the words, "Stay tuned."
The Associated Press checked in with Hilfiger several times that day to get a sense of what it's like to live in his shoes. (Black loafers, no socks, by the way.)
"In the shower this morning, I did think, 'Do I pinch myself?'" he says moments after arriving in his chauffeur-driven Bentley to the morning rehearsal of the awards ceremony at Lincoln Center. He's in a crisp navy suit without a tie, and, quite literally, he comes in bouncing despite the rain that's forcing him to carry a tartan plaid umbrella.
Spending more than a few minutes with Hilfiger, one notices he moves quickly and efficiently.
He makes his way through the labyrinth underneath the stage to catch Diane von Furstenberg, president of the CFDA, as she's wrapping up her own practice session. He ignores his iPhone, which makes the sound of waves crashing, while she's speaking, and applauds for her when she's done — the only one in the room who does.
He goes way back with von Furstenberg, Hilfiger explains, and she was the one who sent him the email with news of the CFDA award. "She was congratulating me, but I had to scroll down to find out why!"
He'd do pretty much anything von Furstenberg asked, he says. And she does: She wants him to attend a dinner for a good cause. He will, and then he asks her to do the same.
A lot of successful fashion people have good causes, he says. His include autism awareness and the Martin Luther King Jr. Memorial in Washington.
After a double-cheek kiss for von Furstenberg, Hilfiger gets a sneak peek at what will be included in his award montage and in the CFDA 50th-anniversary display. It has to be, absolutely must be a navy blazer, says a show producer, and the team is looking for an example of his signature madras prints.
That gets swift approval from Hilfiger, but he doesn't like that his head is cut off in a photo. It's taken care of — just like that.
He wants to know if he can hear a preview of the speech that Vogue's editor-in-chief Wintour will give. That's a partial yes: Wintour's stand-in reads a few lines from the teleprompter, but the rest will be kept as a surprise.
Hilfiger goes to the podium afterward and he makes sure among all the friends and family members he acknowledges, he also thanks his customers. Hilfiger has caught flak sometimes for having a more commercial eye than the industry's pure artistes, but not many of them have that idling Bentley outside.
"OK, let's go," he says, and he's on the move back to the car, settling some logistics about the rest of his day, including just where he and wife Dee will sit during the ceremony, and he ponders where he'll keep the trophy. There's a quick conversation with Kenneth Cole — resulting in more future dinner plans.
Next on the agenda, interviews with foreign reporters at his Fifth Avenue store, a meeting with his corporate backers at Phillips-Van Heusen Corp., a consultation with his design team on collections for September's New York Fashion Week and a 45-minute catch-up with his son, who is visiting from California.
He goes back to the Plaza apartment to put on his tux, which he pairs with formal patent-leather lace-up shoes, and plug in his phone. He's going with the pinstripe one instead of plain black because he wanted "a little more fun."
He sits down on the velvet couch that's bookended by animal-print stools and seems like he takes his first big breaths of the day. He points out the congratulatory peonies sent to him by Kors. Equally lovely flowers from Narciso Rodriguez are in the other room. "The flowers are very nice gestures," he says.
Hilfiger gets up again when his wife comes down their grand carpeted staircase in an orange jumpsuit. She jokes that she chose the bright sherbet colour so that he'll be able to find her when he looks out from the stage.
"You can't miss me in this," Dee says.
But Hilfiger did almost miss the red carpet; he was one of the last arrivals. For all his celebrity and efficiency, not even Hilfiger can control Manhattan traffic, especially on a night that President Barack Obama is holding fundraisers.
"I must have been asked 12 times if I am nervous. I'm excited, I'm humbled, I'm honoured, but I don't think nervous. Should I be nervous?" he says just before he gets inside.
He bumps into model Karolina Kurkova, who is wearing a Hilfiger dress. "He's such a nice guy. He wouldn't have lasted this long if he wasn't," Kurkova says.
Hilfiger indulges the last few photographers right outside the door. He gives a big grin. He's enjoying the spotlight — or maybe more like savoring it.
"This is a wonderful moment in time, but it could be dangerous to think this is the ultimate moment," he says. "It is a great nod of respect, but I have to get back to work."
That will have to wait until after a trip to Mystique.