Ivanka Trump's Most Embarrassing Wardrobe Malfunctions Of All Time

The Trump family's outdated fashion trends have been fodder for some style-starved internet users looking for closet-filling inspiration. Well, they won't find much there, since most of Trump's inner circle looks like they've been styled personally by the president of SHEIN. Take Ivanka Trump, for example. While she used to make headlines for flashing skin in weird peekaboo midriff little black dresses — that even her killer figure couldn't distract from — Ivanka has tried and failed at professional attire. Dare we say, she's even teetering on grandma-core in a May 2025 dress, embellished with gaudy, floral accents.

It seems like the first daughter has always given us a reason to doubt her fashion sense. There's even cause to assume that Ivanka doesn't look in the mirror before stepping out in one of her wardrobe pieces. That's practically backed by evidence, seeing as Ivanka, on multiple occasions, has been called out for her severe, public wardrobe malfunctions.

It looks like her tailor forgot to stitch the final seams into Ivanka Trump's dress, because her army green cap sleeves were flying about during a 2019 visit to Colombia. Some photos revealed how ridiculously large the sleeves were. When the wind lifted the fabric in the air, Ivanka was centered between two green saucers. One X (formerly Twitter) user shared a photo of Ivanka on the platform, amusing: "It has been reported that Ivanka trump fell into a pond full of lily-pads and had to fight her way out in [Colombia] today!"

It must have been cold in the United Nations' General Assembly hall, because Ivanka Trump couldn't hide her reaction under her blouse. At the 2019 UN General Assembly, the daughter of Donald Trump suffered a major wardrobe malfunction, seemingly forgetting to wear anything under her thin, satin button-down shirt and revealing her nipples to the entire room. Social media users didn't let her forget, either. "I guess she was trying to make a couple of points very clear," one X user joked. Another quipped: "Ivanka is abreast of the situation ... " Some have started to believe she is rivaling Melania Trump in the most inappropriate outfit for a professional setting competition.

Ivanka Trump arrived at the 2020 White House Summit on Human Trafficking: The 20th Anniversary of the Trafficking Victims Protection Act of 2000 event in a more conservative wardrobe piece than at the UN General Assembly, but still did not bring her A-game. The former senior advisor to the president donned a white wrap dress that resembled a hotel bathrobe more than formal attire — the brooch didn't do her outfit any justice. One wrong move and the belt could've come loose, likely revealing pajamas underneath. 

While some can only dream of Ivanka Trumps lengthy stems, her towering height sometimes doesn't do her any favors. For example, Ivanka's pastel yellow dress at the 2024 Miami Open quarterfinals was clearly not green lit by her stylist. The pockets seemed awkwardly placed and her sleeves were much too small for her long arms. The whole tailoring of the outfit was off, indicating that Ivanka probably snagged it from the back of her closet, where she keeps the rest of her 2010s wardrobe relics. 

During her father's 2025 presidential inauguration, Ivanka Trump made an accidental political statement with her outfit choice. If you thought Melania Trump's weird twist on her black and white aesthetic was character-esque (think "Spy vs. Spy") that day, just take a gander at Ivanka's look. The businesswoman was at the center of another social media attack; this time, people on X compared her muted teal ensemble to that of the signature uniform worn by the merciless Serena Joy Waterford in the Hulu drama "The Handmaid's Tale." Even sans the social commentary, we think Ivanka could've lost the hat. Not to mention, her daughter Arabella's coat dress looked eerily similar to the coats worn by the wives and the handmaids on the show, which makes the whole family's ensemble just a little too designer dystopian for our liking.