Before Bill Cunningham rode his bicycle around the city taking photos of fashionable New Yorkers for The New York Times, he helped dress some of them as William J., the milliner.
Along with socialites and Old Hollywood stars — Doris Duke, Joan Crawford, Marilyn Monroe and Ginger Rogers among them — his fans included people like Venera Macaluso of Queens, who died in 2018 and went by Netty. Eight of her one-of-a-kind hats designed by Mr. Cunningham are now up for auction as part of a sale ending on March 21.
Styles on the block include a hat resembling a small purple pancake with silk lilies of the valley sprouting from it, a fascinator with stars in gold sequins and black velvet, and a hat with a grasshopper-like bug perched atop flouncy layers of neutral tone silk chiffon.
At the time Mr. Cunningham was making the hats, some sold for $35 and others for $65, he wrote in his memoir, “Fashion Climbing.” Bids at the time of publication ranged from about $150 to $250.
After Mrs. Macaluso died at 93, her son Robert J. Macaluso found the hats on a shelf in her closet. Mr. Macaluso, 72, a retired salesman at the textile house Scalamandré who is now a deacon at Saint Margaret Parish in Madison, Conn., then stored them in tissue paper in his garage.
He explained that his mother’s initial connection to Mr. Cunningham was through her brother-in-law and his wife, who ran in the same social circle as Mr. Cunningham. They invited him to parties and to Sunday dinners at Mr. Macaluso’s grandmother’s house in Queens.
“My grandmother served pasta with veal cutlets,” said Mr. Macaluso, whose father, a New York Times photographic printer from 1965 to 1990, sometimes worked with Mr. Cunningham. “Bill would come over. He was so charming and upbeat.”
Mr. Macaluso said his mother liked to go out with his father or friends to places like Sign of the Dove and Roma di Notte, two Manhattan restaurants that are now closed, as well as to Tavern on the Green and the Plaza Hotel.
“Bill was intrigued with my mother’s sense of fashion,” Mr. Macaluso recalled. “Because of Bill’s enthusiasm, he would sometimes say, ‘Netty, this would look mahvelous on you.’”
Mr. Macaluso’s cousin Barbara Starace, now 80, who was also Mrs. Macaluso’s goddaughter, said she “always looked like a movie star.”
Ms. Starace recalled Mrs. Macaluso wearing the fascinator with stars designed by Mr. Cunningham one New Year’s Eve. Ms. Starace was given another of Mrs. Macaluso’s William J. hats — a pink velvet corkscrew style — after she died.
“I put it on a stuffed toy pig on my bed,” said Ms. Starace, adding that she had never liked wearing hats. “It reminds me of my Aunt Netty.” Mrs. Macaluso also wore a William J. hat, which was very tall and had feathers, to Ms. Starace’s wedding in 1960.
Of the bunch up for sale, that hat — a 13½-inch-high confection of purple silk velvet topped with rooster feathers — is the favorite of Tanner C. Branson, the head of sale for luxury handbags and couture at Freeman’s Hindman, which is holding the auction. He described it as “quintessential William J.”
Other hats for sale include a black velvet fez with rooster feathers, a space-agey black style with netting and a pink straw hat that also has netting and birds made of feathers facing beak to beak.
“People wearing these are very interested in fashion,” Mr. Branson said. “They are interested in being seen, and make a statement.”
When Mrs. Macaluso’s hats arrived at Freeman’s Hindman in Chicago, he added, it was “a bit like Christmas to a fashion history lover.”
Sometimes, a little rhinestone was embedded as a period on the labels of William J. hats. Other labels were folded down at the corners, Mr. Branson explained, in the style of certain couture garments. “Balenciaga did the same thing,” he said. “Coco Chanel did the same thing.”
Like items by high fashion brands, William J. hats are now owned by museums and other institutions. Those with Mr. Cunningham’s designs in their collections include the New York Historical and the Costume Institute at the Metropolitan Museum.
“He had a sense of perfectionism and sense and style,” said Valerie Paley, a senior vice president and director of the library at the New York Historical, which also has a William J. printing plate and label.
Mr. Cunningham’s hats have also been sold on websites like eBay. The site was where Carol Dietz, a retired New York Times art director who worked closely with him, bought a William J. cloche hat with a grosgrain ribbon bow for $135 in 2020.
Ms. Dietz also has several feathers from a collection kept by Mr. Cunningham. “He loved feathers in hats,” she said. Hers are “wrapped in paper so they don’t crumble,” she added.
Steven Stolman, a fashion designer and author, said that at the height of Mr. Cunningham’s millinery career in the 1950s and ’60s, he had called himself “the mad, mad hatter.”
“Every hat had a little wink,” said Mr. Stolman, who wrote the book “Bill Cunningham Was There” with John Kurdewan, a New York Times production artist who worked closely with Mr. Cunningham. Mr. Stolman, a former president at Scalamandré, had worked with Mr. Macaluso at the textile company and helped facilitate the sale of Mrs. Macaluso’s hats by Freeman’s Hindman.
Mr. Stolman said he could hear Mr. Cunningham, who died in 2016, saying “how mahvelous” it was that some of his hats were up for auction. “But then, in a typical self-deprecating way,” he added, “Bill would say, ‘Who would be interested in a bunch of old hats?’”
