The First Lady Wears Naeem Khan at the Cuba State Dinner.

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When President Obama, the first lady and their daughters arrived in Havana on Sunday, it marked the first presidential visit to Cuba since Calvin Coolidge in 1928. Such an occasion demanded diplomacy, behind-the-scenes and publicly (Mr. Obama and Raúl Castro, Cuba’s president, gave a lengthy news conference), sightseeing and a bit of celebration: A state dinner, held at the Palace of the Revolution.

When the important questions of the day — human rights, the future of the American trade embargo, Cuba’s future — were raised (if not settled), a frothier one came to the fore: Cuba was giving a party. What would Michelle Obama wear?

Even well into her husband’s second term, Mrs. Obama’s fashion choices are followed, cataloged and scrutinized, and at state dinners in particular, she has made a habit of her own kind of sartorial diplomacy, often electing designers whose work spans in some way the United States and its guest or host. For a state dinner hosting Canada, she chose the New York-based Canadian-Taiwanese designer Jason Wu; for a China state dinner in 2015, the Chinese-American Vera Wang.

The Obamas arriving in Cuba on Sunday.

Speculation, accordingly, ran to two prominent Cuban-American designers whose work Mrs. Obama has championed: Isabel Toledo, whose canary-yellow dress and coat she wore to her husband’s first inauguration, and Narciso Rodriguez, whom she has worn several times, most recently to the State of the Union address in January.

In the end, Mrs. Obama went with Naeem Khan, the Indian-American designer she has worn often.

“I had sent her a couple of different things,” Mr. Khan said in an interview on Tuesday morning. “I had no idea. You never know what she’s going to wear. I guess I got pretty lucky.”

Mr. Khan is responsible for some of Mrs. Obama’s best looks, including the gown she wore to a state dinner for India in 2009. (Cathy Horyn, then the fashion critic of The New York Times, wrote, “She probably never looked better.”) He has also become something of a family favorite: First daughters Malia and Sasha Obama wore Naeem Khan dresses for their first appearance at a state dinner at the Canada dinner earlier this month. (“I guess they see their mom in all the glam and want to be like her,” Mr. Khan said. “I was very happy when they chose something.”)

The dress Mrs. Obama selected for the Cuban dinner, in a Kashmiri fabric embroidered with an Indian floral motif, is similar to one in the same fabric from the designer’s pre-fall collection. It was a lovely, sprightly choice, less glamorous than what Ms. Obama often selects for such events, but in this case, well suited to the occasion. The dinner’s dress code, Women’s Wear Daily reported, was “casual cocktail,” so Mr. Khan sent cocktail dresses rather than the gowns he is known for. During her Cuban visit, Mrs. Obama has been on a floral kick, selecting a floral Carolina Herrera dress for her arrival in the country.

Mr. Khan does not have a direct connection to Cuba, but he does have an indirect one: He explained that he is in the process of moving his design studio and his production from New York to Miami, where he has a second home. Miami is home to a large Cuban-American population — including the city and county mayors, with whom Mr. Khan is working to set up production facilities and bring jobs.

“This is going to be a game changer for Miami,” Mr. Khan predicted. “After what America has done for me, coming from India, I need to give back to this country.”

About Mrs. Obama, Mr. Khan had nothing but praise.

“She has made my brand and put America back in fashion,” he said. “I would do anything for her.”

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