From High Seas to High Style: VIPs Lose Their Lunch as NYC Sets Sail for Fashion Week

Hilary Swank and Michael Kors.

Hilary Swank and Michael Kors.

Deciding it was time for a break from Arthur Ashe Stadium, Shindigger traded in our tennis racket for mainsails over Labor Day weekend at the Museum of Yachting’s 34th annual Classic Yacht Regatta in Newport, R.I.

It was a Miami-meets-Manhattan crowd aboard Panerai’s VIP spectator ship, where guests such as Alan Zelcer, president of Isaco International, Haute Living CEO Kamal Hotchandani and Alexander McQueen’s Liz Radler, along with husband Robert Souza, were treated to an afternoon on the high seas.

The water was choppy, and the skies were cloudy, but Shindigger had no problem downing two glasses of red before the boat motored past Fort Adams State Park, even as one seasick VIP lost her lunch over the bow.

The small talk ranged from “Where have you summered?” to “Rosé or white?” And one curious Upper East Sider even asked Shindigger where we live.

“Fort Greene, Brooklyn!” we proudly responded, as a dead silence filled the air.

A few hours later, we all repaired to the trendy marina club 41 North for an evening of dinner and dancing. Corporate lawyer Daniel Novela and his wife, Marcella Novela, who sits on Miami Art Museum’s board of trustees, made perfect tablemates.

Shindigger confessed to Ms. Novela we were dreading the fast-approaching onslaught of “fashion month,” as we call it.

“It’s been a very long time since I was at New York Fashion Week,” she replied. “It always conflicts with our European travel plans.”

We noted that Ms. Novela looked right out of a page from Visionaire in her leather harness belt with studs, Margiela suede coat and Halston blouse.

“I love the boat shoes, but I think the women’s outfits could use the most help,” she said about the requisite New England attire. “I sometimes battle with my husband. When I was packing, he said, ‘No, no, no! You have to bring something that’s more preppy.’”

A few chalices of Sangiovese later, Shindigger chatted with Jed Pearsall, son of mid-century furniture designer Adrian Pearsall. He had raced earlier that day and sat across from us with his partner, Bill Doyle.

“A lot of the best sailors in the world are in Newport,” Mr. Pearsall said from behind his cosmo, adding that since this was officially the dénouement of summer sailing, he was ready to move on to autumnal pastimes. “I play polo in Boca Raton.”

As for Fashion Week, “I won’t be going,” he chuckled. “I buy all my clothes at T.J. Maxx or Marshalls.”

How proletarian.

A few days later, at what can only be considered the annual grand début of September’s New York Fashion Week, the Museum at the Fashion Institute of Technology honored Michael Kors with its 2013 Couture Council Award for Artistry of Fashion at a benefit luncheon held in the David H. Koch Theater.

Just as we were about to take a sip of rosé on the outdoor terrace, Shindigger was interrupted. “Excuse me?” Tony winner Nina Arianda said. “Do you know where you’re sitting?”

“It’s on your name card,” we replied.

“Oh, I didn’t get one,” she said, defeated.

Unable to contain ourselves, we gushed, “I absolutely loved you in Venus in Fur!”

“When did you see it?” she asked.

Before you won the Tony,” we replied.

“Oh, good!”

We wanted to inquire how her character had changed, post-Tony, but we were then whisked to our seats, along with the likes of Iris Apfel, Anna Wintour, Doutzen Kroes, Yaz Hernandez, Chanel Iman, Jamee Gregory and Patti Hansen. Shindigger sat with a medley of Palm Beach and Greenwich leading ladies.

“I read The Observer this morning,” one tablemate divulged. “I love that section with the housing. They were too harsh with that Dylan Lauren article.”

Academy Award winner Hilary Swank soon took the podium and delivered a plaque to Mr. Kors, who sported his signature aviator gold-rim glasses.

“He should lose the glasses,” muttered a lady to our right.

After the camera flashes subsided, we caught up with the fashion titan, who had a noticeable glow about him.

“What’s your secret?” we demanded.

“Iced tea, reruns of The Nanny, a secret stash of Doritos and a Thai massage,” he divulged, though he also confessed his stiff neck was the product of a recent trip to the massage parlor.

We pointed out the dozens of fashionable femmes strutting about in Michael Kors designs and asked the man of honor what aspect of his career he was most proud of.

“I’m truly proud of all of it,” Mr. Kors told Shindigger with gusto. “I’ve come a long way since my days at FIT. Everything from being included on the Time 100 and The New York Observer lists to receiving the CFDA Lifetime Achievement Award has been amazing.”

And now he wants to provide similar opportunities for others, like Kim Nguyen, a third-semester fashion design student at FIT, who was named as the first recipient of the Michael Kors Endowed Scholarship (for which he donated $1 million). “Fashion is always about what’s next—and talent. She represents that beautifully.”

As dessert was served, Shindigger skipped the ice cream sundaes and reached instead for a goody bag.

“Oh, sorry! “Press doesn’t get any,” snapped some clueless intern, pouting as though we had broken a rule at preschool.

We nearly decapitated her but decided to just join the stampede for the Koch Theater doors. It was the start of Fashion Week, after all, and everyone was moving on to the next big thing.