Amid the candy-colored Spanish colonial-style facades and vintage cars lining the streets of Old Havana, there is a digital awakening occurring that belies the frozen-in-time appearance of the communist Caribbean island.

Nearly a year ago, one designer found a way to take her hip, local apparel brand—popular with the burgeoning tourist set as well as homegrown residents—worldwide, despite decades of Cuba’s isolation from global markets. In October 2017, Idania del Río’s Clandestina label became the first Cuban brand to sell online—even to the United States.

The move took some finagling, with del Río and co-founder Leire Fernández finding a loophole to sidestep U.S. legislation. Restrictions make the imports from Cuba nearly impossible and very costly, but the duo spent the last several years researching how to get around the embargo. They discovered that the Office of Foreign Assets Control, a U.S. agency that administers and enforces economic and trade sanctions, makes a distinction between the sale of physical products versus services to U.S. customers.

“The law is a little different now, and OFAC allowed some independent Cuban activities—especially ones related to creative industries like design, tech, art… and that’s our gateway,” Fernández says.

The brand’s online products are designed in the Havana studio with digital images uploaded for a manufacturer in South Carolina to screen print on T-shirts from a supplier in Nicaragua. The American manufacturer can then…

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