Trump's Cringiest Comments About The Women In His Orbit (So Far)

U.S. President Donald Trump has made many comments about women over the years. The image he projects of himself is that of a very masculine man, which for him also seems to involve keeping a lot of women around him in his inner circle at all times. From the numerous women who've worked for him to all the wives he's had, Trump is no stranger to women and makes his feelings about them known — whether the words he chooses to express them are appropriate or not.

During a March 2026 speech, the president made a cringey statement about a female colleague when he waxed poetic about Kellyanne Conway, the infamous political advisor to President Trump during his first term as the 45th President of the United States. In a video shared to X, Trump gave a shoutout to Conway, saying that "she's fantastic, she's in there fighting" ... all while seemingly forgetting that Conway hadn't worked for him in years. Which begs the question: Does Trump see all the women in his life as separate people, or simply a roving workforce of blond-haired, MAGA-fashioned shapes that all morph into one singular blob eventually? If his other comments about the women in his orbit are anything to go on, that may well be the case.

There's acknowledging your children are beautiful, and then there's the comments Donald Trump has made about his eldest daughter, Ivanka Trump, whom he had with his first wife, Ivana Trump. In 2004, Donald appeared on a radio show with veteran host Howard Stern, who described a 22-year-old Ivanka as "a piece of a**" (via CNN). Most fathers probably would have been repulsed at that statement, but not Donald. Instead, he agreed wholeheartedly with Stern's words. Of course, this isn't the only time Donald has commented on Ivanka's appearance in a way that seems a little odd for a father-daughter relationship.

When asked if Ivanka had undergone a breast augmentation during a different interview with Stern in 2006, Donald uttered the words: "Why, did she look a little more stacked?" (via Politico). The public, press, and even body language experts have weighed in on Donald and Ivanka Trump's relationship and the inappropriate nature in which this father talks about his daughter, but that hasn't stopped the president from making more crude remarks.

Donald Trump has made his feelings about Ivanka's beauty clear on several more occasions, such as on "The View" in 2006 when he said if he weren't her father, "perhaps I'd be dating her" (via YouTube). That's an icky comment to make about any much younger woman, but to make it about your own daughter is so far beyond the pale it almost makes the Earth change rotation. Considering what we know about Donald's long-term, close friendship with unsavory characters who also have a penchant for much younger women, these comments might not be so surprising — but that doesn't stop them from being both incredibly gross and cringeworthy to make in the first place.

Donald Trump serves a lot of "word salads" where no one knows what he's talking about, and his comments can definitely come across as more stream-of-consciousness than something with actual planning behind it. Yet, he somehow manages to make surprising comments even despite that, including his remarks during a speech where he not only praised White House Press Secretary Karoline Leavitt's beauty and called her a superstar, but said "those lips that don't stop — bop, bop, bop — like a little machine gun" (via The Economic Times).

Commenting on the appearance of a woman who not only works at the same place as you, but actively works for you, is a big no-no in any universe. It's clearly something that women who work for Trump have become used to, but most would agree that it's still iffy even if people are used to it. 

The specifics of Trump's comments are definitely a head-scratcher — what exactly does it mean to have lips like a machine gun? Does that mean they're very strong, or is it something to do with the shape of them? Does it mean Karoline Leavitt is an impressive talker, who says strong words? Does it mean she talks quickly? Or is it truly purely an aesthetic comment that means something only to Donald Trump and the logic in his own brain? We may never know, mostly because Trump isn't a man who tends to explain exactly what he means in an easy-to-follow manner.

Marjorie Taylor Greene and Donald Trump's friendship fallout has been both explosive and well-documented. Before she resigned in January 2026, MTG served as a congresswoman for Georgia and was well known as one of the most highly-valued, outspoken women who worked for Trump. However, things can change quickly in the world of politics.

Since her resignation and condemnation of Trump's administration, the president has made it clear he won't be accepting any calls or other correspondence from MTG — if there's one thing Trump knows it's how to hold a grudge. Even with that, there's been some truly choice comments from Trump about MTG since their feud began. 

At a rally in North Carolina at the end of 2025 (via The Economic Times), Trump referred to the former congresswoman as "Marjorie Traitor Brown," and called her "highly neurotic," making it clear there really is no love lost between him and someone who used to be known as one of his closest allies. Having fallen out over issues with foreign affairs, disagreements over Republican leadership, and the full release of the Epstein files, Trump also referred to MTG as a "rotten apple" on Truth Social.

Despite being a fan at one point, Donald Trump has made several offensive comments about Megyn Kelly — previously one of Fox News' most well-known anchors until she left the channel in 2017. While she's a divisive figure, there are certain things Kelly does consider important that clearly clash with Trump, such as her work investigating sexual misconduct, and her clear break with the Republican administration in March 2026 over the war with Iran.

With these clashes in mind, it's probably not surprising that over the years Trump has referred to Megyn Kelly as a "bimbo" many times, even tweeting it in 2016. After the Republican presidential primary debate in 2015, Trump spoke to Don Lemon for CNN about Kelly's questions as debate moderator, saying, "You could see there was blood coming out of her eyes, blood coming out of her wherever." Public uproar ensued over the comment, which resulted in Trump's political advisor, Roger Stone, leaving his job. Moreover, the conservative outlet RedState uninvited Trump as a speaker at one of their upcoming forums over the sexist remark.

Melania Trump has transformed a lot over the years, from an immigrant model and Donald Trump's third wife to the first lady of the United States. But not all is rosy in the presidential suite, as infidelity rumors have plagued Donald and Melania for years. Furthermore, the president has made inappropriate public comments about his marriage that lead us to believe his union is not so strong.

One comment that feels particularly disloyal is Trump's response to a question about what he would do if Melania — with whom he shares his youngest child, Barron Trump, — were ever to be in a bad car accident and ended up disfigured. Ever sure of his priorities, Donald responded to the 2005 interview with a question: "How do the breasts look?" (via The Week). 

Donald made no comments about his wife's welfare, or what kind of care she might need, just right to the point by asking what her body and general appearance would be like. Granted, Melania Trump's style and looks are one of the most-discussed things about her, but in an ideal world, her husband would care a bit more about her general wellbeing after an event like that.

Even though every parent says they don't have a favorite kid, the favoritism rumors between Donald Trump and his children are rife, with many believing Ivanka Trump takes the top spot. This partisanship didn't help Donald Trump Jr. when he began dating Fox News host Kimberly Guilfoyle — a top figure in Donald Trump's 2024 political campaign.

Allegedly, Donald Trump's rumored distaste for Kimberly Guilfoyle ties back to his rumored favorite child. According to a source who spoke with The Atlantic in 2019, there was tension when Guilfoyle upstaged Ivanka and husband Jared Kushner at a Fourth of July event. Not only that, but in 2021, according to one of Donald Trump's advisors, after finding out that Guilfoyle had decided to back Republican candidate Eric Greitens in Missouri, Trump reportedly asked, "Why the f*** is she working for him?" (via Politico). The source also claimed that Trump thinks "Kim is annoying."

Over the years, Donald Trump has shown that he values Kellyanne Conway — former senior counselor to the president — and still thinks highly of her despite the fact that she no longer works for him. However, he has clashed with her husband, attorney George Conway, who is an outspoken critic of both Trump and his policies. The divide in politics eventually affected the couple, though, and they divorced in 2023.

It's rumored that Kellyanne was one of the few people close to Trump that refused to go along with his narrative that the 2020 election had been "stolen" from him. In fact she wrote about it in her 2022 book, "Here's the Deal," writing that she "may have been the first person Donald Trump trusted in his inner circle who told him that he had come up short this time." Trump was having none of it, and remains firm that he didn't lose the election, but that it was robbed from him.

In response to her book, Trump posted to Truth Social in 2022 saying if she truly admitted that Trump lost the election he "wouldn't have dealt with her any longer" and that she "could go back to her crazy husband." Despite publicly denigrating Kellyanne and taking aim at her then-husband, she and Trump are still close.

Despite Donald Trump's rumored favoritism and the elevated position of Ivanka Trump, she isn't the only Trump daughter. The only child of Donald and his second wife, Marla Maples, Tiffany Trump has had a stunning transformation over the years, but remains less-known than her other siblings. Her parents' relationship was quite a scandal back in the day, with Trump seeing Marla Maples while still married to his first wife, Ivana Trump. Tiffany's birth was also big news at the time.

After she was born, Donald and Maples sat down for an interview with "Lifestyles of the Rich and Famous" in 1994. When asked what traits Tiffany had inherited from him versus her mother, the future president's comments were beyond problematic. While he described Tiffany as a "really beautiful baby," he added that she appeared to have Marla's legs, before motioning two hands to his chest and saying, "We don't know whether or not she's got this part yet, but time will tell" (via Inside Edition). 

Definitely icky to say about your own daughter, and especially icky to openly say you're thinking about the future chest size of a newborn baby, but Donald Trump is well known for his broken-record babbling. Either way, Donald's comments about baby Tiffany should definitely be filed under some of the most grossly cringeworthy comments he's ever said about the women in his life.

Before he was a Republican candidate and the 45th and 47th President of the United States, Donald Trump was known for his appearances on TV and his property empire. Behind the scenes, he enforced odd and exacting standards when it came to his employees. Trump has made it clear that he considers the attractiveness of the women who surround him to be very important, and a reflection on him and his power. 

"We had a big meeting once," a former Trump employee told The New York Times. "I grabbed one of the women in the office and sent her in to get lunch orders. Donald said, 'Not her.' She didn't look great. He got another woman to take the lunch orders. That was purely about looks. He wanted the people in that room to think that all the women who worked for him were beautiful."

That would be problematic enough, but he was also known to keep an unflattering picture of real estate developer and longtime Trump employee Louise Sunshine in his desk to bring out when she did anything he didn't approve of. To make matters worse, Donald referred to this picture as her "fat picture," (via Tampa Bay Times), and actively used it to shame her for not agreeing with him on everything.

Kristi Noem's most inappropriate moments as secretary of homeland security may have contributed to her fall from grace. Her termination from Donald Trump's administration was a spectacular change of heart for a woman who the president was very insistent on giving a job to in the first place. His need for the women representing him to be "beautiful" is well-documented, but in the case of Noem, Trump made his main reason for needing her in his orbit clear: her face.

Having previously done some adverts for the state of South Dakota that featured Mount Rushmore, Noem claimed that Trump urged her to do more adverts about the border, as part of her role as secretary of homeland security. According to The Atlantic, Trump reportedly praised the "beautiful ads" and said, "I want you in the ads. And I want your face in the ads." For Trump, looks are key — especially if you're a woman — and he wanted Noem's looks to sit front and center of his plans for the U.S.-Mexico border and the related immigration policies. Donald has since denied this, but it's not the first time he's explicitly favored a woman just for her appearance, and it's doubtful it will be the last.