New York-ese.
Everybody loves to be told they’re looking good, and it’s very common to tell someone that. You can’t do it too often or it loses its sound of authenticity.
Even more New York-ese:
You’re looking good. I almost didn’t recognize you.
(Translation: You’re looking good. And I love you.)
People of that age and wealth know a lot of people who have had “work done”.
When they say, “She looks good, she really does,” I take it to mean, she’s had enough work done to still fit in and look as youthful as realistically possible.
Trump’s comment, I think was more an honest reflection about Granny Macron’s weight, which to some appears scrawny, but she’s in The Donald’s approval range.