Hats off, Bogie.

The traditional Italian hat maker Borsalino, whose fedora has defined the rough-and-tumble images of Robert Redford, Frank Sinatra and Humphrey Bogart, has a plan to appeal more to women and millennials by pushing into high-end fashion, streetwear and even sportswear.

The recent troubles of the company, which has been rescued financially by a private equity fund, underline the difficulties facing Italian companies seeking scale to stay competitive and grow in the age of globalization.

Entering new markets, targeting new demographics and expanding retail presence all require cash. And even the best-laid business plan can be complicated by a company’s bad baggage, and Borsalino came with plenty of that.

A woman tries a hat inside a Borsalino hat store in downtown Milan, Italy, Wednesday, Jan. 16, 2019. If the traditional Italian hat-maker Borsalino was once synonymous with the fedora, its new private equity owners want to imbue the brand with cachet that extends to couture, sportswear and streetwear for women and Millennials -- without alienating its classic customers and the silhouette that helped shape the rough-and-tumble images of Robert Redford, Frank Sinatra and, perhaps no one more than, Humphrey Bogart. (AP Photo/Antonio Calanni)
A woman tries a hat inside a Borsalino hat store in downtown Milan, Italy, Wednesday, Jan. 16, 2019. If the traditional Italian hat-maker Borsalino was once synonymous with the fedora, its new private equity owners want to imbue the brand with cachet that extends to couture, sportswear and streetwear for women and Millennials — without alienating its classic customers and the silhouette that helped shape the rough-and-tumble images of Robert Redford, Frank Sinatra and, perhaps no one more than, Humphrey Bogart. (AP Photo/Antonio Calanni)
A woman shows a label inside the Borsalino hat factory in Spinetta Marengo, near Alessandria, Italy, Thursday, Jan. (AP Photo/Antonio Calanni)
A woman shows a label inside the Borsalino hat factory in Spinetta Marengo, near Alessandria, Italy, Thursday, Jan. (AP Photo/Antonio Calanni)
A man holds a hat inside the Borsalino hat factory, in Spinetta Marengo, near Alessandria, Italy, Thursday, Jan. (AP Photo/Antonio Calanni)
A man holds a hat inside the Borsalino hat factory, in Spinetta Marengo, near Alessandria, Italy, Thursday, Jan. (AP Photo/Antonio Calanni)

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