The alum of Oscar de la Renta and Carolina Herrera designed Melania Trump’s inauguration dress and has regularly styled the first lady, whose wardrobe choices have been a constant source of controversy since her husband President Donald Trump entered the White House.

For instance, Trump drew criticism for the neon pink Delpozo frock featuring especially voluminous sleeves that she wore to deliver her speech to the United Nations on Tuesday. The dress retails for about $3,000, and Trump wore it as she told world leaders that “no child should ever feel hungry.” Then there were the sky-high stilettos that Trump wore as she boarded a flight to hurricane-ravaged Texas. The footwear choice was seen by some as insensitive since the trip was aimed at comforting those who’d just lost house and home. Plus, a string of high-profile fashion designers have vowed not to work with the Trump administration.

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Pierre didn’t necessarily style Trump’s most polarizing looks, but they show what he’s up against; a highly-charged political climate where the first lady’s fashion decisions are picked apart by her own critics and those of the president.

In a new interview with The New York Times, Pierre talked for the first time about dressing his most notable client and acknowledged the political minefield that is the first lady’s closet.

“What interests me in this relationship is not just finding pretty clothes—a lot of people can do that,” he told the Times. “It’s more about the legacy of this woman. Everybody has a different reaction to what she’s wearing.”

Pierre—who dressed past first ladies Hillary Clinton, Laura Bush, and Michelle Obama in his previous roles at Herrera and de la Renta—seems to revel in the high stakes.

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“Even if I’m not creating the clothes,” he says, “it is very creative to consider how it’s going to be perceived. And when you decide, you divide. I’m not always right. I make mistakes, and same for her. There’s no ‘How to Be the Perfect First Lady’ book. You learn on the spot.”

Then there’s the question of where Pierre shops for Trump—Bergdorf, Saks, Michael Kors, Dior, he says.

And that comes with a whole new set of hurdles.

“What is challenging is when I cannot say what it is for,” he told the Times. “I always ask: ‘Was it already on the red carpet? Did somebody already wear it?’ Because I don’t want her to be on the ‘Who Wore It Better’ list.”