"When I heard that she was doing this", the "Late Show" host said of Melania Trump's unannounced trip to visit migrant children in Texas, "I thought, 'OK, this is what first ladies often do - you go to a troubled area, they see the children, they show that we care. you can't mess that up'".
The president's third wife ditched the $39 coat before getting off the plane in Texas.
When is a jacket not just a jacket?
The first lady herself called for political compromise to end the stripping of children from their parents - the result of the Trump administration's "zero tolerance" policy against illegal border crossings, in effect since May.
The green hooded spring military jacket has the words written graffiti-style on the back. "Do U?" on the back as she returns to Washington from a visit to the U.S. -Mexico border area in Texas at Joint Base Andrews, Maryland, US.
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Trump's decision to head to Texas comes on the heels of a widely-criticized tweet she sent out two days earlier, in which she thanked Queen Letizia of Spain for having tea with her and discussing ways to "positively impact children". The jacket belongs to the Zara's spring-summer 2016 season and is no longer for sale by the company, though a few of the jackets popped up online for resale at a moderate profit for sellers.
She was greeted by Upbring CEO Dr Kirk Senske, who said: "We treat them like our own children".
Her wardrobe touched off an intense media debate as she sported a jacket with the cryptic message, "I really don't care".
"I REALLY DON'T CARE, DO U?" written on the back of Melania's jacket, refers to the Fake News Media.
She visited the Upbring New Hope Children's Center there.
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This is not the first time that Melania Trump and her husband's administration have not appeared on the same page.
But it came after 2,300 children were split from their parents, some in circumstances where border agents informed the parents they were taking the children to get a bath.
"I'd also like to ask you how I can help these children to reunite with their families as quickly as possible", she said.
She later inspected the detention facility's schoolroom and chatted with about 20 young girls and boys who had school folders on their desks.
It's not the first time the first lady's fashion choices have caused a stir.
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However, he made a U-turn yesterday under mounting pressure and when signing the order, Trump said he did it because he "didn't like the sight or the feeling of families being separated". On the wall, was a handpainted American flag signed by the children.