She wore pieces by the Bronx-born designer to the third and final presidential debate.
So what did Melania - now - Trump reply to that 1999 question?
A foreign-born, former supermodel who married an eccentric billionaire is about to become the United States' next first lady.
Melania, a Slovenian former model, was born in 1970 in communist Yugoslavia.
She always said she wanted to go to (Slovenia's capital) Ljubljana to study at the design school there.
Melania began her modeling career when she was 16, and at the age of 18 signed with a modeling agency in Milan, Italy.
Being that her husband will be spending time with dignitaries from across the globe, Melania's linguistic abilities may come in handy at White House functions and events.
Mrs Trump has her own jewellery and skin care line and speaks five languages - Slovenian, Serbian, English, French and German.
Ivana left Donald in 1991 amid rumours he was having an affair with ex-beauty queen Marla Maples, who he'd met in 1989. "As the future president prepares to hold public office and run the most powerful nation in the world, Barron Trump will enter the spotlight as the first son America has seen in a very long time - 54 years to be exact".
Melania has proven in the a year ago or so that largely she has Trump's back.
There's no question Ivanka Trump, 35, is a family woman.
"I pledge to every citizen of our land that I will be president for all Americans and this is so important to me", he added.
And perhaps one of the most important photos of all, Ivanka proudly showed off her "I voted" sticker on November 8 along with Jared and their daughter.
"I don't know that person that would talk that way and that he would say that kind of stuff", she said, before writing if off as "boy talk". But she said he had been egged on by a TV host who was with him on a bus on which he made the hot mic comments.
That appeared to cost her support among women, young voters and minorities - three groups that are critical for Democrats to win big.
Accompanied by his family, as the new American President gave his victory speech at NY, the serene faced Melania donned a garment that seemed like an extension of her tranquil self. "She was excellent at her job (in the campaign)".
Another photo that also was shared around shows Trump's son, Eric, at the polls, seeming to look over at his wife's ballot as well.
"A very traditional social hostess is something I think she will be comfortable with".