Ivanka Trump Outfits That Were Full Of Hidden Meaning

Ivanka Trump makes more statements with her fashion than people might initially realize. In fact, the former first daughter is often donning outfits that are full of hidden meanings. From her early days as a model to working with her dad, President Donald Trump, to her relationship with now-husband Jared Kushner, to her time in the White House, serving as an advisor to the president, or her post-political days, Ivanka is always telling some kind of story through her clothes. Each of these eras was a unique moment for Ivanka sartorially, with marked style shifts. 

Perhaps no era has been so markedly different — and more loaded with meaning — than Ivanka's departure from the White House following her father's first term as president. Once she and Jared left to return to private life and shed their political identities, Ivanka's outfits drastically changed and sent out a new message. Gone were the prim and proper fits; Ivanka was embarking on a much sexier version of herself, and one that was more carefree. It was as if she was daring the public to criticize her for showing leg or for being more risqué. This came with its own message; she was separating herself from the politics (and scandal) of her father. While this is arguably the most interesting of all of Ivanka's eras, each chapter is worth looking at. 

Though Melania Trump was once a supermodel herself, she isn't the only one in the family to get their start that way. Ivanka Trump began modeling in 1997 in a turn of events that would make her even more famous than she already was. In 1998, she walked the Marc Bouwer show at just 17, wearing a dramatic, black dress featuring sequins and a scarf attached to her waist. It was a pivotal moment for her, one in which she was exerting independence from her famous family, about to embark on adulthood. The dark, merlot lipstick and the stony pose, in addition to the very grown-up dress, were her way of saying that she was no longer a kid.

But modeling wasn't something Ivanka intended to do forever. "It's as ruthless an industry as real estate. I used it as an excuse to travel," she told Marie Claire in 2007. "I used it as a way to break up the monotony. I want to be a little bit more serious than that, ha ha!" The era was a significant one for Ivanka, and she spoke out loud and clear through her wardrobe.

Ivanka Trump launched her eponymous fashion line in 2014, starting first with shoes and later moving on to clothing and accessories. On May 29, 2014, she attended the DuJour Magazine's "An Evening Of Glamour" event at the Couture Jewelry Show inside the Tryst nightclub at Wynn Las Vegas. It was a perfect fit, since Ivanka's line included fine jewelry, and she was there to promote her own brand. Ivanka wore a high-collar, burnt orange sleeveless dress with sky-high heels. The outfit marked a new moment for Ivanka, showing her effort at becoming a more professional person, with workwear attire appropriate for corporate women, which was undoubtedly how she saw herself. She had moved beyond the modeling world and was taking herself more seriously. Ivanka had to close the brand in July 2018 due to a conflict of interest after her father, Donald Trump, became president.

While there are some red flags in Ivanka Trump and Jared Kushner's relationship, the couple has been together for a long time. The two married on October 25, 2009,after Ivanka converted to Judaism for Kushner. Her custom-made Vera Wang wedding dress was loaded with special meaning. It was inspired by Princess Grace Kelly, showing that Ivanka was leaning into a traditional, historic look. The gown was also very modest with handmade lace sleeves, giving a nod to her new, conservative faith. But, there was also no shortage of bling in Ivanka's wedding outfit; she wore over $220,000 worth of diamonds from the Ivanka Trump Collection, cementing her image as a rich, fabulous new wife.

In June 2018, Ivanka Trump strolled the White House lawn in a white Emilia Wickstead dress that embodied a new era for her. The midi dress was conservative and modest. It buttoned all the way up to her throat, and Ivanka looked both demure and sophisticated. The dress created an awkward moment for her, though. She and her husband, Jared Kushner, were at the White House to promote an event for American working families, but the dress that she chose to wear cost $2,110. The event was meant to highlight the hardships that working families faced, all while Ivanka wore something prohibitively expensive. 

Ivanka was under much more scrutiny at this point in her life, and her outfits revealed a desperate attempt to fit into the political landscape. She dressed with caution, though not as much as she should have, perhaps. Ivanka did get called out for some scandalous outfits during that era, so there were a few blunders. She worked hard to cultivate a more conservative style, but it was clear that she wasn't interested in making it permanent. Once Donald Trump ended his first term, Ivanka showed no interest in returning to politics.

Ivanka Trump embraced her party girl side after leaving the White House, and showed this loud and clear by rocking a Clio Peppiatt minidress in navy with a corset-style top. Ivanka exhibited this stunning dress while out on the town with husband Jared Kushner in Miami at the American Express Presents Carbone Beach. Ivanka had a big message with this little dress; she was no longer inhabiting the political space. Gone were the conservative midi-dresses and pant suits. She was strutting her stuff in mini dresses, showing off legs and serving big-time party girl vibes. Ivanka was telling everyone through her carefree looks that she wasn't in the Oval Office anymore.

Ivanka Trump sent a confusing message on the night of Donald Trump's second election win in November 2024 by wearing a velvet, blue suit. It was bizarre because traditionally, Republicans opt for red as a party color, while Democrats wear blue. Ivanka's suit reflected a strange sartorial allegiance, sparking curiosity about where her own political feelings landed. At the very least, she may have been trying to come off as bipartisan following the huge hit to her popularity after her involvement in her father's first term as president.

For the Inaugural Ball in January 2025, Ivanka Trump wore a black and white Givenchy gown that had originally been created for Audrey Hepburn in 1954. She was hoping to look more timeless and classic in an effort to rise above the divisiveness of politics, particularly after her and Jared Kushner's unpopular first stint in the White House. The dress garnered so much attention that Hepburn's son, Sean Hepburn Ferrer, spoke to the Daily Mail about Ivanka's dress choice. "It is no wonder that growing up in a family which knew our mother as a household name, she chose to draw inspiration from her, to seek the ultimate elegance and class reference, for an occasion such as this one," he said. Clearly, Ivanka wanted to give the vibe of timeless elegance. 

Ivanka Trump wore an elaborate dress when she attended Jeff Bezos and Lauren Sánchez's wedding in Venice in June 2025. She stepped out with Jared Kushner wearing a pink, strapless Tony Ward gown, and wasn't a bit shy about flaunting her attendance at the controversial wedding. The attention-grabbing dress featured embellished beading in floral shapes with a thigh-high slit, and served to tell a story: Ivanka's message was that she was proud to be affiliated with the world's elites. She's moved beyond the White House, but she's still surrounded by some of the most powerful people in the world.