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On a Monday in early February, Michael Salem was considering some silicone breast enhancers at a booth at the Jacob K. Javits Convention Center in Midtown Manhattan. Part of the location had recently been taken over by Curve New York, a lingerie fair.

The fake breasts were from Nood, a so-called Solutionwear brand that, according to promotional materials, offers products intended “to make all women feel seen.” With a softly feminine design, the enhancers were a modern and subtler version of the bulky breast prostheses that Mr. Salem sold for decades as a retailer largely catering to men who identify as transvestites and wear women’s clothing.

After examining the amps, Mr. Salem, an 82-year-old with a booming voice and a penchant for self-promotion, began giving an Emergency representative unsolicited advice on how to attract customers like his. The company should make its enhancers even bigger, he said, and add nipples to their smooth surfaces.

“Look at the Breast Form Store,” he said, referring to an e-commerce company that sells products similar to those he offers 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 views on sexual and gender identity have evolved, are now used far more often than they were between the early 1970s and the mid-1990s. , when Mr. Salem’s business was in its heyday.

After finishing Nood, Mr. Salem moved to a booth selling Playboy lingerie. He co-led the fair with two home health aides, Barbara Ward, 67, and Rock Corner, 64, whom he treated like friends.

While looking at the Playboy undergarments, Mr. Salem grumbled about his past grudge against Hugh Hefner, which Mr. Salem said began 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 always carries, looking for a photo of an event he had organized at an old Playboy club in New York. He wanted to show it to the employee at the stand.

Mr. Salem opened his eponymous store in 1969 after, as he put it, growing up on the sales floor of his father’s Salem Hosiery in New York, which sold stockings, underwear and accessories like breast pads to society types. Mr. Salem, hoping to attract a younger and more adventurous audience, stocked his own store with racist lingerie and products such as custom breast prostheses made of rubber and later silicone.

After his store opened, Mr. Salem said, it steadily began to attract a certain type of male customer that he had first encountered in his father’s store. These men, he said, told him they were looking for lingerie for their wives, but left with items of clothing in sizes that led Mr. Salem to 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 tall, size 12.’” He said his cousin Harvey Milk, the gay San Francisco politician who was 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 stayed at hotels such as the Waldorf Astoria and the InterContinental New York Barclay. Transvestites until early 2010 could be arrested in New York State for impersonating a woman.

Because Mr. Salem was for decades a rare seller of high heels, lingerie and plus-size dresses, his customers included transgender women, many of whom exercised similar discretion because they also risked discrimination and arrest.

Serving transvestites 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 eponymous talk show. The retailer has also worked with clients on films such as “To Wong Foo, Thanks for Everything! Julie Newmar.”

At its height, the Michael Salem Boutique had locations near New York’s Times Square and in other cities such as Philadelphia and Baltimore. Mr. Salem claimed that the company’s mailing list grew to hundreds of thousands of names.

The store space has since shrunk to a website, but “people keep calling,” Salem said. In addition to breast prostheses, he sells prosthetic vaginas, synthetic wigs, lingerie, heels up to size 16 and clevises to minimize bulges below the waist.

He said certain recent cultural shifts have made it harder for his company to survive: an increase in genderless clothing; clothing and lingerie brands are starting to offer more sizes; the takeover of e-commerce by companies like Amazon. This also applies to his health, which deteriorates as he ages.

Mr. Salem has also generally become less enthusiastic about trends in the lingerie industry. During the Curve show, he walked past stands selling minimalist underwear and eco-friendly stockings. He was also unimpressed by products from a gender-inclusive French supplier to whom he was referred by a Curve representative. “Everyone had pretty much the same things,” he said.

His mood brightened as he approached a booth at Rago, a company that has been making girdles and corsets in Queens since 1945. His father had sold the items at Salem Hosiery. Mr. Salem stopped to talk to Steve Chernoff, who bought Rago in 1997, about long-defunct underwear brands and a possible return of hemmed hosiery.

“A lot of my customers want things from the 1950s,” Mr. Salem said after visiting the stand. ‘Stocks with seams, corsets. They don’t always want to dive into new things.”

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