$20,000 Pants … and Other Adventures in Men’s Luxury Resale!

In a floor-through loft in SoHo one Friday night in January, Vincent Ferraro was selling luxury clothing. Sort of.

On one side of the room, a tattoo artist covered a young woman’s palm in an illustration of a bankroll. Some people flipped casually through the racks of Chrome Hearts and Enfants Riches Déprimés, but Mr. Ferraro — sinewy, with a shaved head and covered in tattoos — didn’t pay them much mind. Instead, he poured shots of Patrón, posed for Instagram photos and occasionally disappeared with one of the several women who had come to vie for his attention.

On the men’s resale clothing site Grailed, Mr. Ferraro, who before the

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