Ivanka Took 'Old Money' A Little Too Literally With This Dated Fashion Moment

Ivanka Trump has always lived an insanely lavish life. Thanks in large part to her famous father Donald Trump and mom, former model Ivana Trump, she grew up wearing designer clothing and rubbing elbows with New York City glitterati and Hollywood's rich and famous while attending high-society events. Becoming a first daughter and senior White House adviser didn't stop Ivanka from flaunting her love of luxury clothing and accessories either. In April 2018, she donned a stunning, $12,888 pink Rodarte gown, one of Ivanka's most expensive outfits ever, for a state dinner honoring French President Emmanuel Macron. The following year, she joined her father at a state banquet hosted by Queen Elizabeth II at Buckingham Palace, wearing a Carolina Herrera gown with an eye-watering price tag of $11,600. And it's not just formal events. 

Ivanka has often been photographed rocking pricey everyday wear too, from a chic pair of $1,490 Oscar de la Renta pants to a white, $2,110 Emilia Wickstead midi dress straight off a quiet luxury fashion-themed Pinterest board. But even with the businesswoman's fashion know-how and considerable resources, Ivanka hasn't been able to avoid a problem that has long plagued the Trump family: Wearing outdated trends. The all-blue look, consisting of a velvet pantsuit and silk button-down shirt that she wore on the night of the 2024 election, was a case in point. The ensemble didn't come off as a modern revival of a 1980s favorite but rather made the first daughter seem like she was about to bust a move to a disco hit at any moment. Unfortunately, Ivanka committed the same fashion faux pas when she met up with some pals for dinner just months later. 

Ivanka Trump's style often makes her stand out in a crowd, typically because she's usually one of the best-dressed people in any given situation. However, that wasn't the case during a gathering with her friends. Ivanka shared a photo of herself surrounded by her pals as they posed together at a restaurant on her Instagram Stories, captioning it: "Happy belated birthday dear @flaviettak!" While she indeed stood out, this time around it was because the first daughter was upstaged fashion-wise by everybody else at the table. 

Ivanka was giving total grandma chic in a sleeveless lavender top with dark buttons. The dated top was the kind of thing we wouldn't be surprised to see on Karoline Leavitt, who has sported plenty of outdated looks during her tenure as White House press secretary, but it's rare for Ivanka, whose chic taste in clothing has even drawn favorable comparisons to Kate Middleton. Unfortunately, this wasn't the only time Ivanka's fashion sense failed her since her father was elected president for the second time in November 2024. 

Just days before New Year 2025, Ivanka made a major style blunder when she went for a cowboy chic look for a date night with her husband, Jared Kushner. The mother-of-three sported a long, brown suede dress, matching knee-high leather boots, a tan jacket, and a wide silver-and-turquoise belt while attending a holiday bash thrown by Jeff Bezos in Aspen, Colorado. We're not sure what the dress code was for the party, but considering Kushner wore a blue button-down shirt, white T-shirt, black pants, and matching dress shoes, we can assume guests weren't required to dress like wealthy ranch owners.