“Everybody back up!” someone called to a crowd of people surrounding the model and actress Christie Brinkley, who was standing near a neatly trimmed lawn on a sunny and hot Saturday afternoon.

Ms. Brinkley had just arrived at Polo Hamptons, an annual cocktail party and polo match held over two weekends in July on the sprawling, private Fishel estate in Bridgehampton, N.Y.

“I’ve always gone to polo throughout my time out here because it is so East Coast,” said Ms. Brinkley, 69, as she sipped from a small bottle of rosé from Bellissima, her wine label, which people were also drinking nearby. “And there are usually some cute polo players.”

The event on Saturday, which drew more than 900 people, was organized by Social Life magazine, a lifestyle publication based in the Hamptons that was celebrating its 20th anniversary. The afternoon attracted a crowd that included Jean Shafiroff, the philanthropist, Lizzie Asher, the president of Macchu Pisco, a spirits company, and Maria and Kenneth Fishel, who own the estate.

As the match began, spectators sat under the crisp white tents lining the field, watching as horses and riders raced past.

Just beyond the seats, there was a row of new BMWs (the carmaker was a sponsor of the event) and a line of cabanas from brands including Oscar de la Renta, Piaget and Permanent Touch Cosmetics, an anti-aging skin spa advertising various treatments.

“When I pulled up, there was a hat that was bigger than the woman that was wearing it,” Ms. Brinkley said. “It is fun to see all the get-ups.”

What were you thinking about when you got dressed?

“Go big or go home, right?”

Shani Grosz

What were you thinking about when you got dressed?

“Coming to the Polo!”

Andre Blount

Do you usually spend time here with the horses?

“The horses get completely neglected by the fanfare, so for me it is the priority.”

Diana Redruello

Later that evening, about 20 minutes away in East Hampton, young women playing flutes in long white dresses stood along a sandy path leading to a benefit at the LongHouse Reserve. (The theme was “Midsummer Dream.”)

A 16-acre landscape garden featuring sculptures by Sol LeWitt and Willem de Kooning, LongHouse Reserve was founded by Jack Lenor Larsen, a renowned textile designer who died in 2020. Mr. Larsen lived on the property and opened it to the public a few days a week, but it is now open five days a week.

The event included a dinner, an auction and a dance party, and honored the artist Mary Heilmann and the author A.M. Homes. Attendees included Candace Bushnell, Cindy Sherman, Renee Cox, Bill T. Jones and Robert Wilson.

“LongHouse has had a summer gala for over 15 years, but there hasn’t been a dinner since before the pandemic,” said Carrie Rebora Barratt, its director. “Tonight was really a comeback after the pandemic.”

The benefit raised more than $650,000, according to organizers. As attendees were leaving, they were offered gift bags of potted herbs including thyme, peppermint and fennel.

What were you thinking about when you got dressed?

“I was thinking about being really saturated with the color because it is super green here.”

Renee Cox

What were you thinking about when you got dressed?

“Well, of course, everybody thinks I was thinking about Barbie, but that actually was just a coincidence.”

Candace Bushnell

What is your dream in the middle of summer?

“Going to bed when it’s still light outside, so actually being in bed, and seeing the sunset, and the trees, and the colors in the sky.”

A.M. Homes

What were you thinking about when you got dressed?

“I just thought about bringing some color into the world.”

David White

The Most Dressed features great outfits from up, down and all around town.