Watch Your Headgear: Ladies Break Out the Big Guns for The Hat Luncheon

Natalie Ross and Michelle-Marie Heinemann.

Natalie Ross and Michelle-Marie Heinemann.

On the first Wednesday in May, a rather large tent pops up behind the Vanderbilt Gate on Fifth Avenue between 104th and 105th Streets with the sole purpose of shielding the over-the-top headgear of 1,300 ladies who lunch, a handful of men and one Martha Stewart from the elements as they duke it out for millinery supremacy at the Frederick Law Olmsted Awards Luncheon—or, as anybody who’s anybody calls it, The Hat Luncheon. At this year’s event, the tent proved unnecessary, as honorees Jenny and John Paulson had pledged a cool $100 million to The Conservancy Fund, the exact dollar figure necessary to ensure perfect weather.

Arriving on the scene, the Transom quickly sussed out an early front-runner in the hat arms race: Carole McDermott, a sprightly darling decked out in heritage pearls and a Chanel suit. She skipped the small-time weaponry and went straight for the nuclear option with a towering scale replica of Central Park strapped to her dome, complete with an adoptable bench.

“I have every year gone a bit bigger, and I’ve never once regretted it,” said Ms. McDermott, who stands at 5-foot-3 sans heels but checked in at close to 7 feet with her choice chapeau, which she said took an estimated three months to put together.

We then found the gorgeous Lizzie Tisch standing contrapposto, surrounded by an iPhoned throng. She was wearing an anatomically correct garden snake made entirely from mother-of-pearl. The “hat” was apparently the handiwork of Aaron Keppel, an artist who, Ms. Tisch was quick to note, is not to be confused with “your grandmother’s milliner,” a sentiment echoed by gal pal Amy Fine Collins, who was wearing a snow-white barn owl on her forehead, precariously perched.

“He’s just the most incredible artist. Look at the detail—the wings were made from tearing up thick stock paper and putting it back together,” Ms. Fine Collins said of Mr. Keppel’s handiwork. “The eyes! Look at the eyes! They’re perfect replicas of the real thing. He even constructs them as they would be found in nature. Breathtaking.”

The Transom had only a moment to acknowledge the breathtakingness of the owl peering over her forehead before Ms. Tisch and Ms. Fine Collins continued almost in unison: “Our park is truly our city’s greatest gift. What better way to tip our hat to it than to literally tip our hats to it?”

Making our way into the tent for lunch, we found Gillian Miniter, former president of the Conservancy’s women’s committee, wearing a fluorescent firecracker above her head. We asked her about the logistics of something so delightfully impractical.

“The real art is getting past your doorman in one of these things without him making some slick remark,” she said, gesturing toward the large group of gathered women who would help raise $3.3 million while nibbling on avocado lobster salad. “People fly in from around the world for this lunch,” she continued. “People slave for months getting their hats ready; people open their checkbooks and really have a chance to make a lasting gesture to the city they love. One hundred percent of the money raised here will go to park programs and initiatives, and I think that’s just great.”

As we eventually teetered out of the tent after one too many white wines, clutching a Tiffany tote bag (the perfect Mother’s Day re-gift) stuffed with Estée Lauder’s finest, the Transom had a hard time disagreeing.