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Three years ago, Chloe Stead and Vanessa Wildenstein decided to organize a ladies’ dinner at the European Fine Art Foundation fair in Maastricht, the prestigious annual showcase of antique works of art. The Old Master category, of course, is a particularly clubby market that can be hard for newcomers to break into. Of the 54 exhibitors in the paintings section of the fair this year, at least half are second-, third-, even sixth-generation dealers. Two-thirds of their galleries were founded before 2000, and 50 of them—over 90 percent—are male-only proprietorships.