What It’s Like to Shoot a Fashion Story in Cuba

This story is part of a weeklong Yahoo series marking one year since the opening of relations between the United States and Cuba.

In 1999, Elian Gonzalez was in Miami and I was on my way to Cuba. I was the newly minted fashion director at W, and we were collaborating with the American art photographer Philip-Lorca diCorcia, one of the most influential photographers working today. He’s known for work that bridges documentary and theater, reality and fantasy, and W was all about artists like that. The entire crew was incredible, in fact: Our model was Guinevere Van Seenus, and we had Dick Page on makeup and Serge Normant on hair. One of the images from the now famous shoot ended up hanging on the wall at the Museum of Modern Art in New York — but getting those shots was no easy feat.

Perhaps unexpectedly, the most difficult part was getting there. We applied for journalist visas months in advance and flew through Canada on some crazy chartered airline that was only allowed to fly in and out of Havana. My seat was literally duct-taped together (I’m not kidding). This, I remember thinking, was fashion glamour.

It was a particularly difficult time in Cuba’s history with the United States. Though our shoot had been planned for months, it happened to land just weeks after Elian Gonzalez was found clinging to an inner tube in the Atlantic waters north of Miami. The two countries were fighting over him, which wasn’t surprising given the history of discord between the two, but the conflict made it a horrible time to be an American in Cuba. Philip wanted to shoot there because it was scenic and different, but also because the faded ’50s architecture, crumbling chandeliers, and broken windows created the perfect backdrop for a photo shoot, and he knew it’d only be a matter of time before someone swept in and turned the whole thing into South Beach 2.0.

My job was to make sure we had all the clothes we needed to shoot Guinevere in every possible location. Basically, I had to smuggle them into the country. Normally, my assistants would send dozens of trunks in advance of my landing, so we’d be ready to go upon arrival. For this shoot, however, we had to carry everything we needed in the two suitcases we were allowed to bring.

Once there, we couldn’t walk on the streets without being stopped by Cuban police demanding to see our IDs. The electricity and plumbing at the locations where we were shooting only worked between 7 and 9 in the morning and 5 and 7 at night. The toilets wouldn’t flush. On the third day, we were shooting at a private residence in Havana when we got word that we needed to shut everything down. The government was sending buses to collect all locals to take them downtown for a mandatory anti-American rally.

Things have obviously changed a lot since then. Americans are free to travel to Cuba, fashion’s obsessed with the place, Chanel is even showing their resort collection in Havana next year, and I’m free to think about what I might like to shoot there should I have another chance. Under these very different circumstances, I’d love to pull together something modern, full of contemporary clothes, instead of the dreamy retro look so often associated with the country. Though the Cuban landscape was beautiful, and our resulting photos very arresting, I can’t deny that shooting in a country where even the simple things were often difficult made a photo shoot with so many moving parts all the more trying. I still love that photo shoot more than anything, but I’m ready for round two.

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