Ivanka Trump's Most Revealing Outfits Prove She's Not Afraid To Take Risks

Stepping away from politics has been liberating for Ivanka Trump in more ways than one. Aside from not having her every move scrutinized by the media and the public, she's returned to her socialite roots since settling down in Florida, where she's often photographed enjoying leisurely walks and soaking in the Miami sun with her husband, Jared Kushner, and their three children. "She is very happy, living her best life," an insider told People in 2024 of the first daughter's life after the White House. 

Going from a public face of her father Donald Trump's administration to Florida tastemaker also meant that the world is once more her oyster, especially when it comes to fashion. Though Ivanka Trump wore some inappropriate outfits when she was a campaign fixture and White House advisor during her father's first presidency, she limited her wardrobe to mostly modest and professional looks. However, now that her ensembles are no longer being viewed through a political lens, the former fashion designer and model has reached for daring, skin-baring looks as frequently as coatdresses and suits.

Of course, this isn't a case of Ivanka embracing a new style, but rather going back to her old one. Ivanka's pre-White House wardrobe included plenty of outfits that showed off her killer legs and stunning figure — something that her mother, Ivana Trump, had apparently encouraged. As Ivanka shared in her 2022 eulogy for the late fashion icon (via WWD), "[Ivana] would often chide me that my miniskirts weren't mini enough. 'Flaunt them while you've got them,' she would always say." And flaunt them she has. Whether it's 2006 or 2026, Ivanka isn't afraid to take risks, as proven by her most revealing outfits through the years.

Ivanka Trump joined Donald Trump in the reality TV world when she debuted as a judge in the fifth season of "The Apprentice." However, she opted for a look that was a little too revealing to pass for business casual when she attended the show's Season 5 finale event in 2006. Though it had a thin, sheer panel on the bodice, Ivanka's black-and-white frock still looked modest enough from the front. The back, however, was an entirely different matter because it was, well, missing.

Ivanka Trump spent 2006 gearing up to transition from fashion model to designer, but her career wasn't the only area where she took the plunge. That year, she favored looks with bold necklines, and among the most risqué was this brown number that came with a V-neckline that dipped to her waist and turned semi-sheer under the camera flashes at the 2006 Met Gala. Ivanka later debuted an even bustier look on the red carpet of a movie screening: a black-and-green frock with sheer long sleeves and a deep scoop neckline.

Ivanka Trump looked radiant with pregnancy glow on the 2013 Met Gala red carpet, but she also appeared to be one wrong, sudden move away from exposing more than she would have preferred in her interpretation of that year's theme, "Punk: Chaos to Couture." She wore a navy-and-green gown with a slit that came up almost to her waist. She paired the dress with strappy heels, an oversized belt, spiky gold jewelry, and black streaks in her hair, but the clashing elements only resulted in confusion and one of Ivanka's most unimpressive looks ever.

Ivanka Trump revealed in a 2025 interview on "The Skinny Confidential Him & Her" podcast that she works hard at the gym to maintain her jaw-droppingly toned figure, sharing that her fitness secret is "that pairing of protein and resistance training and weight lifting." She showed off the ripped abs she achieved from her strict diet and workout regimen in March 2024 when she attended Anant Ambani and Radhika Merchant's pre-wedding festivities in India, looking elegant in a sparkling beaded crop top and a maxi skirt embroidered with daisies.

Just months before she would join Donald Trump on the campaign trail for his first presidential run, Ivanka Trump was at the top of her game as a New York City socialite when she attended a fundraising gala hosted by the Foundation for AIDS Research, better known as amfAR, at Cipriani Wall Street in February 2015. She could have easily played it safe for the event but instead went for a blue and white color-block gown with a cutout on the bodice and a slit that revealed a tasteful amount of skin.

Though she seems to have barely aged, Ivanka Trump's face indeed transformed over the decade separating these two photos. One thing that didn't change, however, was her love for a unique cutout dress that bares lots of skin. She wore one such look to a 2015 Tribeca Film Festival party, rocking a low-cut black and white frock with an asymmetrical hemline and long cutouts on one side. Fast forward 10 years to 2025, and she donned an LBD with cutouts along the waist that bizarrely resembled a worried-looking pair of eyebrows and eyes.

Ivanka Trump turned the entrance to Carbone into her personal runway when she and her husband, Jared Kushner, were photographed having a romantic date night at the celebrity-loved Miami restaurant in May 2024. The first daughter's toned arms and supermodel legs were on display in her skimpy dark blue satin dress, which featured a corset bodice. Kushner, unfortunately, decided to go for a much more low-effort white T-shirt, dark jacket, and black pants combo for their dinner date, which left him looking like her bodyguard instead of her husband.

Ivanka Trump adhered to a strictly leggy dress code when she and Jared Kushner joined the F1 Miami Grand Prix festivities in May 2025, but not every look was flattering. In the photos she shared on Instagram, she looked like her style inspiration was the Oscars statue in a metallic gold minidress so tight we wouldn't be surprised if she had trouble breathing in it. However, she redeemed herself with her second look: a tan crop top and miniskirt that showed a sliver of toned belly and plenty of leg.

Ivanka Trump and her husband, Jared Kushner, took a break from surfing and riding jet skis in Miami to celebrate his brother Joshua Kushner's milestone 40th birthday at New York City's iconic Katz's Deli back in June 2025. In another fashion choice that showed Ivanka can't be bothered with politics, she slipped into an LBD featuring barely-there straps and a risqué skirt with a fringe hem and sheer panels for the low-key gathering. She completed the simple but sexy look with a pair of sky-high strappy stilettos.

Donald Trump might have co-opted red, but his daughter proved who in the family really owns this color when she stepped out in fiery looks following her White House departure. In a May 2024 Instagram photo, Ivanka Trump was giving real-life Barbie as she showed off her svelte figure and beach tan in a red halter-neck number with butt-skimming hem and a bra cup design at the bust. She also got into the holiday spirit for an outing with her daughter Arabella in December 2025 with a red-hot bodycon dress.