"I mean she's a woman and I'm not supposed to say bad things, but really folks, come on. Are we serious?"
HILLARY CLINTON Trump also seized on Clinton's looks throughout the 2016 election and similarly claimed she did not have the right look to be president.
"I just don't think she has a presidential look, and you need a presidential look," he said during a Sept. 6 interview with Lester Holt.
"She doesn't have the stamina," he added.
A month later at a rally in North Carolina, Trump said he "wasn't impressed" when the former Secretary of State walked in front of him during one of their debates.
HEIDI CRUZ Amid the 2016 elections, Trump shared an unflattering photo of Ted Cruz's wife alongside a photo of Melania Trump. "A picture's worth a thousand words," the meme was captioned.
The insulting tweet came on the heels of an anti-Trump ad commissioned by a super PAC -- not affiliated with the Cruz campaign -- which shows the First Lady posing nude in a shoot for GQ magazine.
Cruz slammed Trump's decision to retweet the image, writing "Donald, real men don't attack women. Your wife is lovely, and Heidi is the love of my life."
JESSICA LEEDS Leeds is among several women who have come forward with allegations of sexual misconduct against the President. She claimed Trump groped her in the early 1980s, when they were sitting next to each other on a first-class flight.
"He was like an octopus," she recalled. "It was an assault.
In response, Trump said Leeds, now 74, was not attractive enough for him to grope, as she claims he did.
"Yeah, I'm gonna go after -- believe me, she would not be my first choice, that I can tell you," he said during a 2016 campaign rally.
NATASHA STOYNOFF In the weeks leading up the Presidential election, Stoynoff alleged Trump sexually assaulted her while she was writing a profile on him for People magazine in 2005.
Trump brushed off the allegations as he did with Leeds, encouraging his supporters at 2016 Florida rally to "look at her."
"Look at her, look at her words," he continued. "You tell me what you think, I don't think so."
MIKA BRZEZINSKI In a series of scathing tweets fired off by Trump in June 2017, the President slammed the "Morning Joe" host and mocked the ratings for the MSNBC morning show.
"I heard poorly rated Morning Joe speaks badly of me (don't watch anymore,)" he wrote. "Then how come low I.Q. Crazy Mika, along with Psycho Joe, came to Mar-a-Lago 3 nights in a row around New Year's Eve, and insisted on joining me?
"She was bleeding badly from a face-lift. I said no!"
Her co-host, Joe Scarborough dismissed reports that he partied with Trump on News Years, claiming he and Brzezinski were actually at Mar-a-Lago to set up an interview with the Commander-in-Chief.
Brzezinski has long been vocal critic of Trump -- at the time, she had equated his presidency with a "dictatorship."