For the most part, Ivanka Trump is known as a very fashionable woman. Sure, she had that unfortunate period where she ran around in some unflattering suits as she tried to follow in her father’s footsteps. Other than that, though, most of us remember Ivanka from her days as a fashion model and how her modern wardrobe (think throwback couture meets modern influencer) is quite flattering on her figure.
However, even someone as beautiful and fashionable as Ivanka Trump can make some serious sartorial mistakes. And when someone this chic makes a fashion mistake, it creates some cringeworthy moments to remember. Want to revisit the times that Ivanka’s clothing left us wondering, “what were you thinking?” Keep reading to discover her craziest wardrobe malfunctions!
Dress or political commentary?
Ivanka Trump never seemed that interested in politics. Left to her own devices, she would likely have avoided the White House altogether. But she supported Donald Trump on the campaign trail and accepted his offer to become one of his official advisors. From then on, pretty much anything she said or did had the potential to become a political statement. And that included what she wore, as she belatedly found out in 2025.
By the time of Donald Trump’s 2025 presidential inauguration, Ivanka had signaled that she wanted to focus on her family and avoid politics altogether. She still attended the inauguration, though, and she made the mistake of wearing a green outfit that looked strikingly like the outfit worn by Serena Joy Waterford in Hulu’s The Handmaid’s Tale. That show adapts the original novel and presents a fictional world where men have completely taken over America and reduced women to the status of powerless servants.
Given how many feel about Donald Trump (who has made a number of statements about women that many seem offensive), some felt Ivanka we trying to make a political commentary here. As for us, we just think she was having a bad fashion day…like, she looks like she’s headed to Oz and not an inauguration!
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Sleepy time for Donald Trump’s little girl?
Part of Ivanka Trump’s service as an official presidential advisor was attending a number of major functions. This included the 2020 White House Summit on Human Trafficking: The 20th Anniversary of the Trafficking Victims Protection Act of 2000. She seemed to understand that this was a solemn event and that she should avoid the kinds of flashy clothes she used to wear on the runway. Unfortunately, Ivanka seemingly took the idea of “dressing down” a bit too literally!
You see, she wore a white wrap dress that didn’t really look like a dress. No, it looked for all the world like she was wearing a bathrobe. This made it look like she was attending this major event in the goofiest possible clothing. Plus, we couldn’t help but think that Ivanka looks like she is about to bust right out of these clothes if she moved too quickly, and that might be even more embarrassing than dressing in a would-be bathrobe (albeit an expensive bathrobe) for the whole world to see!
Is that Ivanka Trump or a couple of UFOs?
It’s important to remember that Ivanka Trump used to be a fashion model. As such, she typically has a good eye for clothing and knows when to take a risk on a particularly wild outfit. But even veteran fashion models can’t predict the weather. And on one occasion, the wind turned what would have just been a fun, adventurous little dress into a total wardrobe malfunction.
We’re talking, of course, about the time she wore a green dress with oversized sleeves for her 2019 visit to Colombia. On a normal day, those sleeves might have looked cute, like she wanted to turn her arms into statement pieces. Unfortunately, the wind picked up, and the sleeves were immediately caught in the breeze.
Visually, this made it look like her body was about to be carried away by a couple of UFOs. Alternatively, she looked like a princess so ready to kiss a frog that she brought her own lily pads with her!
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Tall woman, little dress
Pop quiz: How do you define a wardrobe malfunction? It’s not always a matter of wearing a crazy outfit. In some cases, a person might be wearing a really cute outfit, but one that is completely out of proportion with her body. And that’s exactly what Ivanka Trump discovered when she wore a yellow dress to the 2024 Miami Open quarterfinals.
On its own, the dress looks cute, with fashionable pockets and some playfully frilly sleeves. There was just one problem: it was way too small for Ivanka’s tall frame. This, combined with its poor tailoring in general, meant that those cute pockets and other features looked chaotically placed all over her body. Just like that, one of the most fashionable women in the world came across like a child barely able to dress herself!