One of the most fun and well-known American hat designers is Benjamin B. Green-Field, AKA Bes-Ben. Born in Chicago in 1898, Green-Field and his sister Bessie (she was the “Bes” and he was the “Ben”) opened their first hat boutique on Chicago’s State Street in 1920, eventually expanding to four more locations in the area. Heralded as “Chicago’s Mad Hatter,” he famously crafted whimsical and elegant hats for women, including such celebrities as Lucille Ball, Marlene Dietrich and Elizabeth Taylor, as well as Chicago socialites.

By the 1940s, the Bes-Ben style had shifted from traditional, stylish hats to surreal and amusing designs. As with many milliners of the time, the rationing of the war years led him to embrace non-traditional materials. His hats were decorated with items such as kitchen utensils and napkin rings and figures such as miniature dogs, cigarette packs, bugs, skyscrapers and doll furniture. The hat that he made for Hedda Hopper to wear to the premiere of the film “The Razor’s Edge” was even topped with actual razors! 

The milliner’s panache extended to his personal style. He was known for his extensive wardrobe and the decorative home items he would collect on his world travels. He loved to dress up and was fond of brocade jackets, cashmere and jewelry. His shop on Michigan Avenue was decorated with pillows that he had brought back from his travels and was a popular social location. 

Green-Field’s sense of humour, combined with his high design skills and use of unique materials, made his work incredibly sought after. During a WWII-era interview, the designer was quoted as saying, “Anything that makes people laugh at this point in world history may be said to have its own excuse for being.” 

He managed his business incredibly well and had a penchant for business. 

“Every summer, he would hold a sale where everything would be $5, an amazing deal considering that most of his hats sold for more than $100,”  said Jessica Pushor, Costume Collection Manager at the Chicago History Museum, in an interview for Classic Chicago Magazine. “People would line up in the middle of the night for a chance to grab a hat flung out to the crowd by Green-Field himself. It would take him an hour and a half to empty his entire store of around 400 hats, and then the shop would close for several weeks for a staff holiday. Green-Field would then leave on one of his famous around-the-world shopping trips; he is said to have been around the world more than fifty times.”

Bes-Ben’s success allowed Green-Field to be a philanthropist. He founded and endowed the Benjamin B. Green-Field Foundation in 1987 in order to improve the quality of life for children and the elderly of his hometown of Chicago.

To this day, Bes-Ben designs are in high demand by collectors. One of his pieces, ‘Independence Day,’ was sold at auction for a record of $18,400. The hat was adorned with an unfurled American flag with red, white and blue firecrackers and stars. 

Over the years, Bes-Ben millinery has been collected and preserved by the Chicago Historical Society. His first exhibit there was a 200-piece showing in 1976. In 1984, they sponsored another exhibition, ‘The Wit and Fantasy of Benjamin Green-Field,’ which displayed his memorable personal wardrobe, home items and hats. When the Historical Society was renovated and expanded in 1988, it included a new Benjamin B. Green-Field Gallery and a collection of his hats are stored in their vaults. The Indianapolis Art Museum also owns a large collection of Bes-Ben hats.