On a Monday in early February, Michael Salem was contemplating some silicone breast enhancers at a booth inside the Jacob K. Javits Convention Center in Midtown Manhattan. A section of the venue had recently been taken over by Curve New York, a lingerie trade show.
The fake breasts were from Nood, a so-called solutionwear brand that, according to promotional material, offers products intended “to make all women feel seen.” With a soft feminine design, the enhancers were a modern and more subtle version of the ponderous breast forms Mr. Salem has sold for decades as a merchant who has catered largely to men who identify as cross-dressers and wear women’s clothing.
After examining the enhancers, Mr. Salem, an 82-year-old with a booming voice and a penchant for self-promotion, began giving a Nood representative unsolicited advice about how to attract customers like his. The company should make its enhancers even bigger, he said, and add nipples to their smooth surfaces.
“Take a look at Breast Form Store,” he said, referring to an e-commerce business that sells products similar to those he offers and that younger brands like Nood have tried to modernize. Many items at the Curve show were marketed as tasteful, inclusive, aspirational and “sex-positive” — words that, as notions of sexual and gender identity have evolved, are now used far more than they were between the early 1970s and mid-1990s, when Mr. Salem’s business had its heyday.
After wrapping up with Nood, Mr. Salem moved to a booth showcasing Playboy lingerie. He navigated the trade show alongside two home health aides, Barbara Ward, 67, and Rock Corner, 64, whom he treated like friends.
While eyeing the Playboy undergarments, Mr. Salem grumbled about his past grudge against Hugh Hefner, which Mr. Salem said started because Mr. Hefner, who died in 2017, refused to run ads for Michael Salem Boutique in Playboy magazine.
Then Mr. Salem spent several minutes searching one of the three Android phones he has at all times for a photo from an event he had hosted at an old Playboy club in New York. He wanted to show it to the employee at the booth.
Mr. Salem opened his namesake store in 1969 after growing up, as he put it, on the sales floor of his father’s, Salem Hosiery in New York, which sold stockings, undergarments and accessories like breast pads to society types. Mr. Salem, hoping to attract a younger and more adventurous crowd, stocked his own store with racier lingerie and products like custom breast forms made of rubber and, later, silicone.
After his store opened, Mr. Salem said, it started to steadily attract a certain type of male customer that he had first encountered at his father’s store. These men, he said, would tell him that they were looking for lingerie for their wives but would leave with garments in sizes that made Mr. Salem suspect the items were actually for themselves.
“We did everything clandestinely,” Mr. Salem said of conversations he had with such customers. “You know, ‘What size stocking would you like for your wife?’ ‘Super long, size 12.’” He said that his cousin Harvey Milk, the gay San Francisco politician fatally shot in 1978, told him that these customers were most likely straight men who found a sexual thrill in dressing as women.
Many did so in secret and “would have separate apartments for their cross-dressing,” Mr. Salem said, or would stay at hotels like the Waldorf Astoria and the InterContinental New York Barclay. Until the early 2010s, cross-dressers could be arrested in New York State for impersonating a woman.
Because Mr. Salem was a rare seller of high heels, lingerie and dresses in larger sizes for decades, his customers have also included transgender women, he said, many of whom practiced similar discretion because they also risked discrimination and arrest.
Catering to cross-dressers and transgender customers earned his business attention in tabloids and from television hosts like Phil Donahue, who had Mr. Salem as a guest on his namesake talk show. The merchant has also worked with costumers for films like “To Wong Foo, Thanks for Everything! Julie Newmar.”
At its peak, the Michael Salem Boutique had locations near Times Square in New York and in other cities like Philadelphia and Baltimore. Mr. Salem claimed the business’s mailing list grew to include hundreds of thousands of names.
Its retail footprint has since shrunk to a website, but “people keep calling,” Mr. Salem said. In addition to breast forms, he sells prosthetic vaginas, synthetic wigs, lingerie, heels up to a size 16 and gaffs for minimizing below-the-waist bulges.
He said certain recent cultural shifts have made it harder for his business to survive: a rise in genderless attire; clothing and lingerie brands’ starting to offer more sizes; the takeover of e-commerce by companies like Amazon. So has his health, which has declined as he has aged.
Mr. Salem has also become generally less excited by lingerie-industry trends. At the Curve show, he walked right past booths displaying minimalist undergarments and eco-friendly stockings. He was equally unimpressed with products from a gender-inclusive French vendor he was directed to by a Curve representative. “Everybody had sort of the same things,” he said.
His mood brightened as he approached a booth for Rago, a company that has been making girdles and corsets in Queens since 1945. His father had sold its items at Salem Hosiery. Mr. Salem stopped to chat with Steve Chernoff, who bought Rago in 1997, about long-defunct undergarment brands and a possible return of seamed stockings.
“Plenty of my customers want things from the 1950s,” Mr. Salem said after visiting the booth. “Seamed stockings, corsets. They don’t always want to get into the new things.”
