Ivanka Trump Outfits That Meant More Than We Realized

Ivanka Trump has been First Daughter of the United States twice. She was active in her father's presidency the first time around, but we can't say the same for his second presidency. In a 2022 statement, she said "I love my father very much. This time around, I am choosing to prioritize my young children and the private life we are creating as a family. I do not plan to be involved in politics," per Fox News. 

Now, the former model has pivoted to being active on social media and quiet on the topic of her dad. Through her many phases and career changes, though, Ivanka has been consistent in her love of fashion. And sometimes, her clothing choices speak in ways that she doesn't.

Ivanka has always been deliberate about how she dresses, and it's clear that she focuses on looking good and expressing herself through what she wears. However, some of her outfits over the years may have had special meaning. Consequently, focusing on what she chooses to wear may give more insight into what's going on behind the scenes, and many of her outfits may have had a hidden agenda or a special message.

For many years, Ivanka Trump was known for her wild modeling looks, but that doesn't mean the heiress ever planned to model long-term. As she divulged in an interview for New York Magazine in 2006, fashion was never her deepest passion. "Modeling was never an endgame for me," she said. "It was never what I wanted to do. I just wanted out of boarding school, where I was bored to death." As for her true aspirations, Ivanka said that she hoped to go on to work in the family business. "I've known, basically since I was cognizant, that I would go into real estate. There's never been any ambiguity about that," she added.

Because of this, Ivanka's choice to step out of runway clothing and step into corporate wear in the mid-2000s was a very big deal. It not only marked her commitment to a new career, but also signaled her transformation from model to businesswoman. Reflecting on this change in the same interview, Ivanka noted, "Now that I'm working in this field, there's not much leeway. I dress really conservatively during the week; I have to take it to another level, so every workday I wear a suit." She went on to opine that showing too much skin in the workplace "really just isn't appropriate." In that sense, her wardrobe choice was a carefully considered part of her new professional image. 

On October 25, 2009, Ivanka Trump and Jared Kushner got married. Leading up to the ceremony, Ivanka converted to Kushner's Orthodox Jewish faith. And, as an Orthodox bride, Ivanka hoped to find a wedding dress that revealed as little skin as possible. To make her bridal dream into a reality, she sat down with none other than wedding dress designer, Vera Wang. Wang understood her vision and started sketching.

Reflecting on this project in a conversation with The New York Times, Wang later revealed that Ivanka "was actually very much about being covered and I seized on the chance to do a dress that wasn't naked and very Hollywood." The designer's solution was, ultimately, to model Ivanka's gown off of Grace Kelly's stunning wedding dress. Like the late princess' gown, Ivanka's boasted lace sleeves that hid her shoulders from view. Wang said that she used a trio of laces to perfect the look.

Ultimately, the designer was so pleased with the results that she confessed to hoping that Ivanka's look would become a larger trend. "Nothing would make me happier. I've been doing strapless dresses for 15 years. It's tiring," she told the publication. Ivanka also seemed thrilled with the final product. With the dress hugging her shoulders and loose curls framing her face, the bride looked very glamorous, while embracing the modest type of look encouraged by her new faith.

As a former model and fashion designer, Ivanka Trump's wardrobe was clearly still important to her even when she turned her attention to politics. Of course, what's more important than the inauguration that would kick off the presidency that she would be a part of? It's clear that Ivanka took the inaugural ball seriously — donning a glistening champagne-colored gown by Carolina Herrera.

The choice to be dressed by Herrera was particularly important. The designer has a history of dressing women in politics, and first ladies. She dressed Jackie Kennedy Onassis, her daughter Caroline Kennedy, and Michelle Obama. "It is an honor to dress the first ladies of the country and it's something to do for the United States. It's not for myself. It's for the public," Herrera told the Associated Press (via NBC News).

In an interview with Glossy, Herrera called Ivanka Trump "a very special woman," noting that "she loves fashion" and "everything she wears looks fabulous on her." At the inaugural candlelight dinner, Ivanka continued the tradition of wearing designers that have been known to dress first ladies. She wore Oscar de la Renta, who dressed Nancy Reagan, Laura Bush, and Hillary Clinton.

Ivanka Trump's faith has touched many aspects of her life beyond her wedding day, impacting everything from her private spirituality to her public image. As she told Vogue in 2015 (via ABC News), "We're pretty observant, more than some, less than others. I just feel like it's such an intimate thing for us ... I am very modern, but I'm also a very traditional person ... I really find that with Judaism, it creates an amazing blueprint for family connectivity." 

Ivanka wore her Orthodox Jewish beliefs on her sleeve in 2017 when she and her father, President Donald Trump, embarked on a diplomatic trip to Israel. During the state visit, Ivanka put her faith front and center via her wardrobe. Dressed in a long navy dress and a small fascinator, Ivanka engaged in the Orthodox tradition of Tzniut, or modesty. The combination of a head covering and a long billowy dress allowed Ivanka to embrace her religious beliefs for all to see.

Interestingly, though, this public display of religion marked a significant departure from the private way that Ivanka has approached conversations around her faith in the past. Previously, she has refused to discuss Judaism with media outlets like CNN, feeling that the topic was too personal. On this trip, however, she posted a photo of herself praying on Instagram. "I am grateful ... to leave a private note of prayer," Ivanka wrote in the caption.

Just because Ivanka Trump practices Orthodox Judaism does not mean she ignores the protocols of other religions. On a 2017 visit to the Vatican, the first daughter wore a long-sleeved black dress and a lacy black veil. Although not everybody understood this choice of attire, it's believed that Ivanka was just trying to follow the Vatican's strict rules around clothing. As Stephanie Grisham — Melania Trump's then-communications director — told CNN at the time, "Per Vatican protocol, women who have an audience with the Pope are required to wear long sleeves, formal black clothing, and a veil to cover the head."

Melania, who was also present at the visit, made headlines with her iconic black Dolce & Gabbana long-sleeved dress and dramatic black gown. Apparently, the first lady was particularly enthused about the visit. Per Grisham's conversation with CNN, "She personally wrote a letter to the Pope asking to go. Princess Diana and Mother Teresa have both visited as well." 

Although it's unclear whether Ivanka also reached out to Pope Francis personally, she did make an effort to respect the head of the Catholic Church during her time at the Vatican. This sets her apart from Cherie Blair, former U.K. Prime Minister Tony Blair's wife, who dramatically broke protocol by wearing white on a 2006 visit with Pope Benedict XVI.

In 2019, Ivanka Trump traveled to Morocco to promote the Women's Global Development and Prosperity Initiative. There, she met with Princess Lalla Meryem, Foreign Minister Nasser Bourita, and others to discuss women's economic empowerment. During the visit, she wore different conservative outfits, including a light grey jacket and pants set, which featured intricate embroidery. 

The then-White House specialty media director, Carolina Hurley, shared the special significance of Ivanka Trump's outfit on X, formerly known as Twitter, (via Express) writing, "Fun fact: the designer of Ivanka Trump's outfit yesterday, Fadila el Gadi, runs an institute in Morocco that teaches underprivileged children the art of embroidery."

A year earlier, in an interview with Al Jazeera, el Gadi said, "Opening a school that teaches embroidery was not only my dream but also a necessity given how this art is dying. ... This not only helps conserve the tradition but also gives these kids a hope for the future because otherwise they had nothing to look forward to." Surely, choosing to work with this particular designer was Ivanka Trump's subtle nod to the initiative on which she was working.

On February 2, 2023, Ivanka Trump shared a photo of herself dressed for a 1920s party on Instagram. Wearing a white, Bob Mackie fringe dress, she looked as glamorous as any flapper. However, what only Ivanka's biggest fans noticed was that her dress of choice was not just any random piece. In fact, it had previously belonged to Ivanka's mother, Ivana Trump, who had died seven months before.

Ivana had once worn the fun white dress to a Studio 54 party, which she had actually attended with Ivanka. Photos of the event show the mother-daughter duo smiling and giggling together as they enjoyed their evening out. With this in mind, it's possible that Ivanka donned the dress in order to recall a happier time when Ivana was still alive. At the very least, it was a spectacular tribute to someone who Ivanka loved and admired deeply.

Indeed, Ivanka's posts on social media show that Ivana Trump's death was heartbreaking. In December 2022, the first daughter reflected on her mother's death in an emotional Instagram carousel of Christmases past. "The loss of a parent is one of life's very painful passages for which one is never fully prepared. It hits at the very core of your being. And it takes a good amount of time to emerge from how it dislocates you," Ivanka wrote. 

While Ivanka Trump acted as an advisor to Donald Trump during his first time as president, she took a hard turn when he decided to run again. Speaking exclusively to The List in March 2024, political science professor at Occidental College Caroline Heldman explained that Ivanka's pivot to social media influencer was likely an attempt to fix bridges she had burned by being so closely associated with her dad and his politics. She called Ivanka's carefully curated social media presence "her own campaign to re-enter high society." According to Heldman, "Her social media frames her as a spirited family woman, curated to reach a wide audience across the political spectrum."

One way to reach more folks across the political spectrum is to appear more worldly, experienced, and open-minded than her father does. In March 2024, Ivanka shared a series of photos of her in traditional Indian attire on Instagram at the famed wedding of Anant Ambani and Radhika Merchant in India. Of course, wearing this attire was appropriate for the occasion, but the notion that Ivanka is trying to portray a version of herself on social media that is very different from anything associated with her father does suggest that there may have been a deeper meaning to sharing so many photos of this ensemble.

Throughout the 2024 presidential election, Ivanka Trump carefully avoided the campaign trail and most events related to Donald Trump's presidency. She did, however, make an exception for the Republican National Convention. Just days after the assassination attempt against her father at a campaign rally, Ivanka attended the RNC and stood alongside her sister, Tiffany Trump. Donald's two daughters stood behind him, both wearing white suits. The image was striking and a clearly deliberate choice on Ivanka and Tiffany's part. 

The sisters were dressed in a color that represented peace and provided a contrast to the violence that was central to the election at that time. Furthermore, some people believed that the choice of white suits was actually meant to coordinate with Donald's white bandage, covering his wound on his ear from the assassination attempt. Their presence in the matching hue did draw more attention to the bandage, which was surely positive in the eyes of Donald's campaign. 

When Ivanka Trump attended the fête at Donald Trump's campaign headquarters on election night, her ensemble for the special occasion caused quite a stir. She wore a velvet blue suit, a choice that many people believe put Ivanka Trump's true feelings about Donald Trump on blast. 

Donald is known for wearing a red tie, the color that is synonymous with the Republican party. Blue is the color typically associated with the Democratic party. Commenters on X were quick to point this out. "'Blue' represents the Democrat Party. Perhaps she was sending a secret message that she voted for Kamala [Harris]!" one tweet read. "Why is [I]vanka Trump wearing a democrat shade of blue? And she's standing well away from Trump and the rest of her family," wrote another X user.

Ivanka's choice to wear blue may have felt like it wasn't important. However, she clearly puts plenty of thought into her outfits. It seems like an obvious choice not to wear blue on election night if you're rooting for a Republican. Since Ivanka was absent for nearly all of the campaign trail, this was quite a noteworthy ensemble.

In 2017, Ivanka Trump surely didn't anticipate that she'd be picking out another outfit for her dad's inauguration eight years later. Yet, when Donald Trump's second inauguration rolled around in 2025, many drew comparisons between Ivanka Trump and Princess Catherine of Wales because of the first daughter's head-to-toe green ensemble. Ivanka wore Dior — specifically, a duplicate of a Christian Dior Bar suit from the 1940s. The skirt suit with a matching hat and black gloves certainly looked vintage, and perhaps that was the goal — a "Make Fashion Great Again" kind of thing. But even when they were first popular, the world was on the heels of World War II, and this over-the-top look was viewed as out-of-touch by many. Incidentally, Ivanka herself is also viewed as out-of-touch by many.

There's no question that Ivanka knew what she was doing in choosing a vintage-inspired ensemble that looked plucked out of history books. For others, though, this style felt like it was plucked out of a different book: "The Handmaid's Tale," to be exact. Plenty of people on social media compared this look to what Yvonne Strahovski wore as Serena Joy on "The Handmaid's Tale" series. In fact, many found the resemblance so uncanny that they insisted it was deliberate. "She has to be doing this on purpose right?" one Instagram user asked. "It's 100% intentional" said another. It's unclear whether this was, in fact, intentional, but if not, it was definitely a misstep.

For the 2025 Liberty Inaugural Ball, Ivanka Trump wore a white strapless gown with black embroidery that she paired with black gloves. The dress was inspired by the one worn by Audrey Hepburn in the 1954 film "Sabrina." The choice to pay homage to the late actress in this way was reportedly important to Ivanka.

"Audrey Hepburn has long been a personal inspiration to Ivanka," the first daughter's representative told Page Six. "She views it as a great privilege to honor her legacy in this way and is incredibly grateful to the team at Givenchy for bringing this moment to life." 

Stars are often not exactly pleased to be associated with the Trump family. In this case, Audrey Hepburn's son spoke out about Ivanka Trump's controversial inaugural ball gown and stayed fairly neutral while honoring his mother. "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 — the inauguration and the 32nd anniversary of our mother's passing and, most of all, Martin Luther King's day," Sean Hepburn Ferrer told the Daily Mail.