President Trump has long defined himself through photographs. But now that he’s in the White House, he’s learning that they can define him too.

As a business executive and later a reality TV star, Trump used carefully staged photographs to define his brand. The cover photo of “The Art of the Deal,” his best-selling book, showed him looking handsome, confident and rich while posing on top of the world in New York City.

In the White House, the trappings of the presidency have given Trump’s images even more power. At the same time, he’s photographed every time he heads out in public, and the results don’t always play to the message he wants to send.

MORE: The Roots of Donald Trump: a Life in Pictures

One photograph of Trump meeting with an all-male group of Republican lawmakers to discuss the health care bill was slammed by critics who noted the changes the White House sought would affect women’s health. It quickly went viral on the Internet and became something of a meme.

Below, TIME looked at photos from the President’s first 100 days in office that showed the power of the image to strengthen — and undermine — Trump’s image.

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