Ivanka Trump Will Never Live Down These Embarrassing Outfits
For a woman in the public eye, fashion is not simply about what she wants to wear. Her clothes, and even hair and makeup, sometimes serve as a nod to her interests, values and ambitions. However, not every stylistic choice is executed perfectly, no matter if it's intentional or unintentional.
Ivanka Trump's insanely lavish life has given her access to plenty of flattering outfits, but like many Republican women, her fashion choices have occasionally missed the mark. While she's not the only member of the Trump family who likes outdated trends, Ivanka's mishaps stand out as one of the younger female relatives. Some of Trump's fashion mistakes are pretty embarrassing, and it seems like she has a lot to learn if she wants to put an end to it.
Her pantsuit's designer is a staunch Trump critic
In April 2020, Donald and Ivanka Trump held an event to inform small businesses about the Paycheck Protection Program. The first daughter wore a blush pink jumpsuit with long sleeves and a thick belt to complement her figure. The only problem is that the jumpsuit's designer, Gabriela Hearst, is not a fan of Donald Trump and has refused to lend anything to Melania. She told The Wall Street Journal, "If they want to wear the clothes, they can buy the clothes." This wasn't the first time Ivanka wore Hearst's clothes in the White House, which is a very strange choice to make as Trump's daughter.
This green dress made her look like an elephant in the wind
In September 2019, Ivanka Trump wore a dark olive-green dress with large, billowing sleeves in Colombia. The figure-hugging dress wasn't an issue to wear indoors, but it became one of Ivanka's most embarrassing wardrobe malfunctions when she stepped outside. As the wind blew, the sleeves went up from her arms in circles around her shoulders. They also bumped into Colombia's vice president on her left and the minister of national defense on her right. One Redditor user compared Trump to lizards in the Disney movie "Holes" and wrote, "When you have work at 8 but have to attack Stanley Yelnats at lunch."
This grand opening dress looked like an unfinished disco ball
The eldest Trump daughter went to the grand opening for the Fontainebleau hotel in December 2023 and looked inspired by its shiny architecture. Ivanka wore a long strapless dress with a black velvet upper half and a shimmery bottom half. The dress is definitely one of Ivanka's more awkward pieces, but the back part not having any silver makes the dress look like an unfinished disco ball.While the dress went well with her makeup and showed off her figure, Ivanka would've been better off wearing a shimmery dress or a dress with a completely shimmery skirt.
Her Western outfit in Wyoming had clashing elements
Ivanka Trump and Jared Kushner enjoyed themselves on a trip to Wyoming in the summer of 2025. Ivanka recapped the trip in an Instagram carousel that included photos of her and her husband embracing and smiling. Trump wore a multi-colored beaded mini skirt with long fringes and a pair of white cowgirl boots. Her long legs looked toned and nicely tanned, but they couldn't distract from the clash between her skirt and boots. While wearing a Western look in Wyoming is a charming idea, Ivanka could have figured out what goes well together.
This Audrey Hepburn-inspired dress lacked Old Hollywood glamor
When her father had his second inauguration ball in 2025, Ivanka Trump wore a replica of the Givenchy dress Audrey Hepburn wore in the 1950s movie "Sabrina." The designs on Trump's dress weren't as intricately detailed as the ones on Hepburn's dress. The president's daughter also wore black velvet gloves, instead of white ones like Hepburn did. Netizens on X were quick to express their disapproval. One user said, "It's look cheap compared to the one worn gracefully by the legendary and beautiful Audrey Hepburn." Another wrote, "The embroidery on Ivanka's dress looks like off-the-rack summer casual wear."
She didn't understand the assignment for Lunar New Year
In February 2026, Ivanka posted about Lunar New Year on X with an image of herself in a white blazer. The large-collared blazer suited her pretty well, but her outfit missed one important detail. Red is commonly worn on the Lunar New Year because of its association with prosperity in Chinese culture, while white symbolizes death. One person on X said, "the way you aren't supposed to wear white on Lunar New Year because it will bring mourning, death, and funerals..." While Ivanka Trump had the right intentions in 2026, she'll hopefully take notes on what colors to wear in the future.