6 Ivanka Trump Outfits That Completely Missed The Mark

Ivanka Trump works hard to maintain her polished and poised public image, and she rarely puts a stylish foot wrong. However, despite the many ridiculously expensive outfits Ivanka has in her wardrobe of designer duds, she still manages to commit a major fashion felony from time to time.

It has to be said that Ivanka still has a long way to go if she ever stands a chance of beating Kimberly Guilfoyle in the inappropriate outfit stakes. But, in fairness, that's a super high bar, and few mere mortals could compete. Questionable clothing does run in Ivanka's blood, though. Ranking the most tragic Trump family outfits is a challenging task, with so many options to choose from. Her late mother, Ivana Trump, was famed for her glitzy and garish get-ups. Meanwhile, the less said about Donald Trump's voluminous, ill-fitting, baggy, panted suits, the better.

Still, given her modeling and fashion mogul background, you'd think Ivanka would really know better. Her track record proves otherwise, and the former first daughter has rocked some style shockers over the years. From design disasters to frumpy fails to couture catastrophes, we've selected six of Ivanka's outfits that completely missed the mark.

Ivanka Trump was running late for the Guggenheim Museum's Young Collectors Council Artist's Ball in December 2006. So, she quickly slipped into her sateen nightie, grabbed an old net curtain, wrapped it around her arms, and rushed out of the house. Well, that's what it looked like, at least. Apparently, though, her look was by Giorgio Armani — who sponsored the event — proving that even the esteemed Italian designer can commit crimes against couture.

Armani is also not afraid to go against the grain, even if it does ruffle some fashionista feathers. Designers Zac Posen, Christian Siriano, Marc Jacobs, Tom Ford, Phillip Lim, and Derek Lam all balked at dressing Melania Trump when she became first lady. However, Armani had no such reservations. "That's my job; why shouldn't I dress a beautiful woman if she asks me to?" he told WWD in January 2017. "This goes beyond politics."

Meanwhile, Ivanka's love of Armani stretches beyond his fashion line. He's also part of her beauty regimen when attending important events. "For major occasions, I will get my hair and makeup professionally done. I can sit and answer emails and I stand up ready for the night! I like to wear Giorgio Armani's Maestro Fusion Makeup," Ivanka told New Beauty in September 2015, adding she also adds a bit of Tom Ford, Chanel, and Nars.

The Carolina Herrera silver metallic dress Ivanka wore in January 2017 cost a whopping $5,000. Given that it appeared to be made of tin foil, the price tag was pretty eyebrow-raising. It was also controversial, causing a storm of social media backlash.

Ivanka posted a pic of her in the gown on X, formerly Twitter, alongside a tuxedo-clad Jared Kushner. They were heading off to the swanky Alfalfa Club dinner and grinned happily at the camera, seemingly without a care in the world. However, that soon changed as Ivanka's tin foil timing was terrible, to say the least. The photo was shared on the weekend that Donald Trump caused outrage by issuing an executive order barring refugees from entering the U.S. for 120 days and residents from seven predominantly Muslim countries for 90. Chaos broke out at airports, and protests were staged across the U.S., leading to detractors accusing Ivanka of being a modern-day Marie Antoinette and totally out of touch with reality.

"Let them eat cake!" one X user commented on the photo. "@IvankaTrump's tone deaf, heartless tweet as hundreds of thousands take to streets tonight to protect Muslim refugees from deportation," another wrote. "You're a disgrace to humankind. The apple doesn't fall far from the tree," a third raged.

Jared Kushner and Ivanka Trump were hoping for some la dolce vita in the Eternal City in September 2019. "When in Rome," she captioned a photo of them posing on a rooftop. Trump attempted to capture old-school Hollywood glamour. Her set and softly waved hair was totally on point, and her makeup was flawless. However, Trump's beige crepe gown was more caped crusader than Grace Kelly. Oh, and the gold metallic belt could have been stolen straight from Wonder Woman's wardrobe.

Meanwhile, Jared, clad in a tuxedo and bow tie, stood stiffly by his wife's side with a fixed smile in place. All in all, the couple was reminiscent of a Madame Tussauds exhibit.

They were in town to attend the wedding of socialite Misha Nonoo and Jared's buddy, über wealthy oil heir Michael Hess. Jared's little bro, Josh Kushner, went to college with Hess, and he was along for the ride, too, with his wife, Karlie Kloss. Rounding out the VIP guests, Prince Harry, Duke of Sussex, and Meghan Markle, Duchess of Sussex, were among the crowd jostling for some champers and cake.

In December 2020, Ivanka Trump, clad in her very best Gilead green, channeled Serena Joy Waterford from "The Handsmaid's Tale." Ivanka's long-sleeved dress was fittingly modest, with a jaunty bow on its high neck. Although, she mixed things up by allowing her hair to hang loose and free. Ivanka's seeming homage to the "traditional values" advocate didn't go unnoticed or unappreciated. "She knows exactly what class she plans on belonging to. That's fun. Best case scenario I'm gonna be a Martha but I will probably just be working cleaning up nuclear waste," a commenter on X wrote.

Serena from the Handmaid's Tale on the left. How Ivanka Trump dressed to visit Bucks County PA today. This is a clear cry for help. pic.twitter.com/3hrHz2CY78

— Benjamin Young Savage (ᐱᓐᒋᐱᓐ)  (@benjancewicz) September 14, 2020

Years later, critics were still drawing stark comparisons between the dystopian novel and the Trump administration's perceived aims. "Haven't you all read Handmaid's Tale (all events based on factual events across world). With it looking like 50-50 men-woman supporting Trump-Harris. If he gets in, I suspect men will get arms to control women. Be afraid, be very afraid America," a doomsayer warned in 2024.

Ivanka was in Chester County, Pennsylvania, for a series of cozy fireside chats. She fielded questions about Donald Trump's response to the COVID-19 pandemic and failed 2016 campaign promises, among other subjects.

Ivanka Trump went all-out "I Dream of Jeannie" in November 2022, giving Barbara Eden a run for her money in a powder pink two-piece with sparkly silver crystalized trim and a mock neck top. Ivanka had popped out of her bottle for the evening to attend her little sister's wedding rehearsal dinner. "Ready to celebrate @tiffanytrump and @michaelboulos !!" Ivanka captioned a photo of her, Jared Kushner, and their three kids, Arabella, Joseph, and Theodore Kushner.

It's safe to say that the social media fashion police were not fans of Ivanka's get-up. "It looks like she made it herself out of a Christmas tree skirt she found at Dollar General," one officer wrote on X. "She has no grace and no taste!!! I mean really, who would of let her leave the house like that!!! It looks like something dragged out of a Salvation Army basement dated 1960 Halloween costumes!!" another opined. "Not sure if I like Pepto Bismol's new fashion line," a third quipped.

Ivanka ditched the pink and plumped for blue to attend the big day. She wore a floaty chiffon number with a long scarf wrapped over one shoulder. Arabella was dressed in a princess dress in a matching hue, and Joseph and Theodore were clad in dark suits and huge blue bowties. Meanwhile, Jared dusted off his trusty old black tux once again.

Ivanka Trump went all-out va-va-voom in May 2024 with a super short and racy, scarlet, satin, baby doll-style dress. Her long, tan legs looked amazing, and Trump undoubtedly has the body to make the dress pop. However, the teen Barbie look was somewhat off-kilter, given that she and Jared Kushner were attending a friend's wedding in Valle de Bravo, Mexico.

Thankfully, Ivanka packed another, more nuptials-suitable dress. Her alternative was a scarlet Cristallini floor-length gown with a plunging split front bodice. "Celebrating love and the magic of Mexico," she captioned a photo of her posing with Jared, who, unsurprisingly, was dressed in his tux.

Ivanka and Jared's Mexican getaway allowed them to enjoy a short break from the rising speculation that she's planning a return to politics and a place by Donald Trump's side if he's voted back into the White House on November 5. "They went on a long-planned weekend celebrating a friend's wedding, far away from the fabricated gossip swirling around of an imminent return to politics in DC," a source told the Daily Mail. Another shared, "The couple remains focused on their family and private lives."