Angel Lazaro, 29, was hanging out with his friends (who call him Mayito) at Bar Roma, on the rooftop of a 1920s building in Old Havana. Mr. Lazaro hadn’t ended up at the bar from seeing it on the street. There was no sign outside indicating that a ride up in a rickety open-air elevator would lead him to one of the city’s most interesting watering holes.

Inside, the scene consists of creative types mingling with tourists over mojitos and rum cocktails. “To me, that was an indicator that Cuba was changing,” said Rose Cromwell, a photographer who has traveled to Cuba for over 12 years.

When Ms. Cromwell visited the bar, there was no bathroom. The residents living down the hall opened their homes to patrons for a small tip, a transaction in keeping with part of Cuba’s economy; many people run bed-and-breakfasts, restaurants and even clandestine clothing shops out of their houses.

In a country where clothing options are limited by a lack of imports, cultivating a singular style can be challenging. “People will bring clothes in bundles from Miami, Panama or Mexico and sell them up from their homes,” Ms. Cromwell said.