5 Outdated Trends Ivanka Trump Was Caught Wearing

Ivanka Trump has long fit into the world of fashion, whether it was as a fashion week guest, a runway model, or the designer of her now-defunct eponymous brand. Her personal style has hit some highs and a few lows, and some of her looks, though they may not have been particularly cringe-worthy, are notably dated. 

What does it mean to say something looks dated? A few things. For starters, it can practically have a time stamp on it — you can look at an image from a certain time period and know by the outfit when the photo was taken. Or it can mean that the outfit looks like it was from a bygone era and verges on costume-ish. There are a number of examples when the Trump family has chosen outdated styles, and spoiler alert: They involve more than one instance of Ivanka wearing skinny jeans when they were not on trend. Don't get between this girl and her stovepipes. Unfortunately, that's not the only era-inappropriate clothing that Ivanka has rocked before.

Ivanka Trump's November 2024 election night look was controversial for more than just its style. Republicans and supporters of her father, Donald Trump, traditionally wear red or something neutral to support and celebrate their candidates. Really anything goes — except for blue. That's the color for Democrats. But politics and potential messages aside (yes, other Ivanka Trump outfits have had hidden meanings as well), this look raised eyebrows for another reason. It looked like a replica of a suit Gwyneth Paltrow wore to the 1996 MTV Movie Awards (above, right). She wore the Gucci suit, designed by Tom Ford, with a blue button-up shirt underneath.

Actually, Paltrow herself decided the look was so good that she decided to revisit it in 2021, when she wore an updated version, still Gucci, but this time designed by Alessandro Michele.

When Ivanka wore the look, however, it wasn't a cool retro moment; it simply looked like something someone else had done really well. Twice. The look went viral for all the wrong reasons, namely that wearing blue — and a vivid shade no less — had people questioning her loyalty to her father.

Ivanka Trump has a pretty strong hair game. Her stunning hair transformation has evolved over the years, with her dabbling with a short bob and chocolate brown locks. But for the most part, she has stuck to long, blonde-highlighted strands, which she wears either sleek or in loose curls. Except in the '90s, when she briefly dyed her hair blue, as described in her mother Ivana Trump's memoir, "Raising Trump." (Ivana insisted she dye it back to its normal shade immediately.) Ivanka said she was in her "punk phase" and listened to a lot of Nirvana.

The socialite revisited the hairstyle for the 2013 Metropolitan Museum of Art's annual gala, wearing blue streaks as an homage to the theme, Punk: Chaos to Couture. Per the Daily Mail, Twitter users had a field day making fun of Trump's so-called edginess when in reality she comes across as very buttoned-up and strait-laced.

It was 2006, the year Facebook allowed open registration from anyone, "Borat" bowed at the box office, Donald Trump and Rosie O'Donnell's feud began, Shiloh Jolie-Pitt was born, and 24-year-old Ivanka Trump was hitting the town in empire-waist tops and fitted bottoms, an early aughts specialty. The cleavage-baring satin babydoll top reeks of 2006, especially when paired with black pants, which were a going-out staple of the late '90s and early 2000s. 

The gold babydoll lingerie-style top paired with bootcut jeans, as Trump did in 2006 for a party in N.Y.C., is a combination that screams early 2000s. Though bootcut jeans re-emerged in 2024, this look still has a timestamp from decades prior.

The ensembles are a far cry from the more refined, polished styles that she wore when her father was first elected to the White House and she took on the role of advisor, and Ivanka sported them when they were already on the cusp of being outdated.

Crop tops and high-waisted jeans definitely had a moment sometime before the first Donald Trump presidency. But skinny jeans fell out of favor before her dad took his post in the Oval Office, so when Ivanka Trump wore the combination of a striped cropped sweatshirt and high-waisted skinnies to a disaster relief visit in North Carolina in October 2024, the look fell flat and looked passé. While stovepipe styles had a resurgence in fall '24, they looked freshest paired with non-belly baring styles like sophisticated jackets.

And cropped tops, though still widely worn in fall '24, looked best paired with some of the more fashion-forward denim cuts, such as barrel legs or baggy jeans. It's a study in proportions, and unfortunately, Trump didn't get this one right. Also, we have to question whether a belly-baring look is appropriate to wear to a disaster relief effort to show support for those on the ground. 

Pure Nightclub opened in Las Vegas in 2004 in Caesar's Palace, and it was the club in Vegas for celebrities to frequent. Early 2000s notables that went to the club included the ultimate pair of wealthy socialites at the time, Nicky and Paris Hilton. So, it's no surprise that Ivanka Trump chose to host her 25th birthday party at the venue in 2006. 

But what was less on-trend and of-the-moment was Trump's choice of outfit, a '60s-inspired look. For starters, the bouffant-y style hairdo and thick black headband looked like she had images of Brigitte Bardot and Barbarella on her inspiration board. Then there's the short sequin shift dress and pointy-toe knee-high boots, which made her look like a bit of a go-go dancer.

We can't help but feel like she should've been celebrating her youth, not trying to channel a washed-up performer from the '60s.