Ivanka Trump's Most Scandalous Outfits Of All Time

Ivanka Trump, while usually polished and stylish, has worn a few shocking and scandalous looks over the years. It's not that she looked bad or that the outfits themselves were ugly, but they definitely made a statement, and some people thought they were inappropriate for the occasion.

Ivanka rocked some of these scandalous get-ups while her dad, Donald Trump, was in the White House, adding an additional element of indiscretion. At other times, Ivanka wore them to parties, and while the world stage wasn't as rocked, the look was scandalous nonetheless.

Ivanka isn't the only Trump woman who has faced heightened scrutiny over her choice in attire. Her sister, Tiffany Trump, has emerged in some outfits that just didn't work. And all of the Trump women, from Melania to Lara, have been guilty of making makeup mistakes. Of course, we're all guilty of that, but when you're on camera as much as this group is, those awkward moments are widely publicized. Likewise, all eyes (and judgements) are on Ivanka when she emerges in something shocking.

To celebrate Tiffany Trump's wedding to Michael Boulos, Ivanka Trump arrived in a pink, two-piece skirt suit. While the outfit itself was lovely, many people thought the combo was a scandalous choice for someone else's wedding celebration, and drew attention away from the bride-to-be. 

"Can you believe Ivanka Trump turned up to poor Tiffany's rehearsal dinner dressed like this??? UGH! I don't know if a dress could show more dislike for a younger sister than this?" one person wrote on X, formerly known as Twitter. Many felt like the fact that Ivanka's shoulders and abs were exposed was too distracting for a family wedding.

In November 2017, Ivanka Trump traveled to Japan and met with then-Prime Minister Shinzo Abe. While speaking about empowerment for women at the World Assembly for Women, Ivanka wore a pink Miu Miu miniskirt and jacket. While the pieces were cute, they were the wrong choice for the occasion, and some were uncomfortable with how short her skirt was. 

"Skirt is [too] short for a meeting with any PM," one person commented on X. "Pretty sure a skirt to at least the knees would actually be appropriate for an international meeting," another noted. In the end, her skirt's length ended up distracting from her message.

There's an old fashion maxim that states that women should choose to emphasize either legs or cleavage, but never both. However, in May 2024, Ivanka Trump attended the Carbone Beach party in Miami Beach and wore a very short, plunging red dress. 

A beach party certainly isn't the worst place to show a little skin, but her dress was considered a tad skimpy to some. "A little short, isn't [it]? Is that your daughter's?" one person commented on Instagram. While the jab might be a mean-spirited, Ivanka clearly chose both legs and cleavage for the Carbone Party. 

In May 2018, Ivanka Trump shared a photo of herself with her son, Theodore, when she was working in the White House as a senior advisor for her father, Donald Trump. She added the caption, "Love it when Theodore comes to visit me at the office." While the sentiment behind the photo was very sweet, some felt her skirt was completely wrong for a professional political work space. 

"Only Ivanka would use her own [kid] to post a picture where she can show off her legs, in a skirt that's much too short for a woman her age," one person wrote. Others noted that it was her place of work, and such a short skirt wouldn't fly in any other office space.

In 2012, Ivanka Trump and Jared Kushner attended the White House Correspondents' dinner together. While Ivanka looked stunning, she had a lot going on with her dress. The beaded ensemble was sheer in areas and featured one of the lowest necklines she's ever worn. This event was before her father's first presidential campaign, and Ivanka and Jared were there as celebrities rather than part of a political family. Nonetheless, the dress was a very sexy choice for the occasion.