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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.

Stead, the global head of Old Master private sales at Sotheby’s, and Wildenstein, herself a fifth-generation member of a prominent art-dealing family, struck upon the notion of a sort of ladies’ club to counter the old boys’ network. “The purpose is to create an environment of mutual support and exchange,” Stead told me of the dinner, which has since become a yearly event, “and to introduce women working in our field who might not know each other.”

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The original attendees included Laura Kugel, from the sixth generation of the Galerie Kugel antiques dynasty and a member of the TEFAF board of trustees. Over the years, other guests have included Sotheby’s specialist Calvine Harvey; second-generation gallerist Laura de Jonckheere; Valentina Vico, director of the family gallery Benappi; Italian dealer Miriam Di Penta; and Esther Bell, deputy director of the Clark Art Institute in Williamstown. “TEFAF is such a feast for the eyes,” Bell told me, “but it’s also a place for convening.”

While TEFAF has become somewhat less of a boys’ club in recent years, it remains an old-money clique. Last year, the foundation’s board of directors appointed Dominique Savelkoul as managing director, the first woman to serve in that role in a permanent capacity. For Kugel, who joined the board of trustees in 2020, perhaps the most meaningful step forward was the appointment of gallerist Alessandra Di Castro as chair of the antiques section, the largest at the Maastricht fair. “It’s recognition of her expertise and hard work, but also of her leadership capacity,” she told me. The fair, while always celebrating its history, has also made an effort to bring in emerging dealers. In 2008, they added the Showcase section, intended as a launching pad for newer exhibitors to the main part of the fair. Only recently did participants even have to reapply, though it seems to be somewhat of a formality; their past participation is taken into account in the selection process. Many longtime club members have exhibited alongside each other at Maastricht for decades—and sometimes their fathers before them. Jonathan Green now mans the corner booth for the gallery established by his father, Richard Green, one of the founders of TEFAF in the 1980s; likewise David Koetser, whose father was among the fair’s founders. Of course, many of the newer dealers enter the business with advantageous pedigrees. While Di Castro struck out on her own in 2009, she hails from Rome’s most prominent antiquarian family. Francesca Antonacci, who co-founded Antonacci Lapiccirella Fine Art in 2012, is a fourth-generation antiques dealer. Andrea Lullo’s gallery is less than a decade old, but he belongs to the third generation of an Italian art-dealing family. Jorge Coll, who became C.E.O. of Colnaghi after it merged with his gallery, is the son of a Spanish art dealer. Cédric Pelgrims de Bigard’s gallery, started in 2013, is located in his family’s 12th century castle in Belgium. And Sotheby’s Elisabeth Lobkowicz comes from a Czech noble family, one that boasts a collection of 1,500 Old Master paintings housed in a palace in the Prague castle complex.

Indeed, most of the field’s newest entrants cite passion when asked what drew them to Old Master paintings. “There are so many stories in early modern art that remain to be written,” said Bell, who teaches graduate students at Williams College. “There’s steady interest in the field.” Many female scholars are particularly interested in uncovering unknown female artists or finding misattributed works by them—a trend in the marketplace that, one advisor told me, some male dealers are reluctantly embracing in order to make sales.

In any case, the next generation is certainly not going into Old Masters for the promise of riches. The category has shrunk in the past decade, which has made it a lot more competitive for dealers as the number of active buyers has dwindled and more of the best works are placed in museums. Global sales of European Old Masters dropped 54 percent from 2014 to 2024, from $838 million to $384 million, with 95 percent of lots selling for less than $50,000, according to The Art Basel & UBS Art Market Report 2025. By comparison, sales in the global art market overall dropped only 17 percent during that same time period, from $68.2 billion to $57.5 billion. Established dealers have responded to the increasingly constrained inventory by closing ranks: It’s not uncommon for them to purchase paintings together at auction, which allows them to better manage costs. They don’t do this secretly so much as discreetly. They have “affinities,” Kugel told me, to the “detriment of new players.” The Maastricht ladies’ night dinners were conceived, in part, so that a new guard could forge alliances of their own, while also welcoming outsiders into their insular world. “Being women in our 30s and 40s, it’s harder for us to simply absorb the way things have always been done,” Kugel told me, while being self-aware about the advantages of her birthright. “It’s easier for us to do things differently.” Fresh blood, after all, is a key element in the lifecycle of collecting, with young dealers helping to attract new generations of buyers. “Younger modern and contemporary art collectors have a growing interest in Old Masters, as if it completes their collections and their education in the arts,” said Di Penta. “This is very encouraging. Ten years ago we were saying, Who is going to buy our paintings? They’re all dying. We’re not saying that anymore.”