The Wildest Runway Looks Ivanka Trump Wore During Her Modeling Career

Ivanka Trump has pursued a number of career paths, beginning with modeling as a teenager. Other jobs on her resume include jewelry, clothing, and handbag designer; real estate mogul; and author. She also served as an adviser during her father Donald Trump's first White House tour, but for his second round in the Oval Office, Ivanka refrained from stepping back into the political sphere. Instead, she wanted to focus on her three children with her husband, Jared Kushner.

Let's zoom in on Ivanka's career as a model. Her towering height gave her a leg up in the modeling world, as did her famous father's connections. Her first big gig was in 1996 at age 14, modeling for Tommy Hilfiger. The following year marked her catwalk modeling debut. As is the case for any model, you don't always get to choose what you wear. And that was certainly the case for the young Trump, who wore some seriously wild runway looks during her modeling career before it ended in 1999.

In April 1997, Ivanka Trump strode the catwalk for the fall/winter '97 Marc Bouwer show. The South African designer, who rose to fame after working with fashion industry innovator Halston, was known for his skills with draping. Arguably his most famous dress was the white satin halter gown that Angelina Jolie wore to the 2004 Oscars, which Sydney Sweeney famously re-wore for the 2024 Vanity Fair Oscars after party.

Bouwer was also known for using daring proportions and bright colors. Both of those signatures were evident in the look Trump strutted down the runway in. The giant earmuffs and over-the-knee boots were certainly a study in excessive proportion, while the head-to-toe red elements definitely didn't shy away from the vivid shade. Even the makeup, both eyeshadow and lips, were shades of ruby. Though red eye makeup can be daunting for most of us, teenage Trump actually pulled the look off like a pro.

Born in 1949, Jean Charles de Castelbajac has had an illustrious career in fashion spanning decades. He has been the artistic director of Max Mara, Benetton, and Courrèges, and he co-founded the label Iceberg. He's dressed everyone from Elton John to Mick Jagger, Madonna, Katy Perry, Lady Gaga, Farrah Fawcett, and even the Pope. In 2024, the French fashion icon was tasked with dressing the clergy for the re-opening of Notre Dame Cathedral in Paris.

He's known for colorful, cartoon-like elements, which were also on display for his fall/winter 1998 show, held in Paris. Ivanka Trump modeled one such piece, a white gown that had Western-inspired fringe down the front and colorful bird motifs along the train down the back. Trump didn't fare too badly with her makeup. She appeared bare-faced with a red geometric shape around one eye and a light stain on the lips. Other models had colorful shapes etched on their lips, cheeks, and eyebrows, but the placement of Ivanka's combined with her upswept hair brought to mind David Bowie's Aladdin Sane era.

Though French fashion designer Franck Sorbier isn't very well known stateside, he is a well-regarded institution in the French design sphere. Ivanka Trump had the privilege to model for the icon in March 1999 at his Paris pret-a-porter presentation. Sorbier, known for his theatrical presentations, loves to dabble in strong, bold designs that emphasize the female form. Such elements were visible in Trump's wild runway look, which converged a number of themes, including a modern take on masculine dressing — by way of a two-piece suit with very short shorts — and a 1920s vibe with the hair, makeup, and fur stole.

This show was near the end of Trump's short-lived catwalk career. "Modeling was not an endgame for me," she explained to Marie Claire in 2007. Rather, it was a means to make money (she had to pay her own phone bill — cue tiny violin) and a way to see the world.

Along with the above fashion powerhouses, Ivanka Trump also modeled for Versace and Thierry Mugler, both considered provocative, formidable designers in the late '90s. Here she is pictured at two of Mugler's shows: the spring/summer 1999 collection, held in October 1998, and the autumn/winter 1997/'98 haute couture collection, presented in July 1997. She joined a bevy of bold-faced names in the industry that also sashayed down Mugler's catwalks over the years, including Naomi Campbell and Cindy Crawford. 

For these two presentations, it wasn't the fashion that was completely wild; it was the hair and makeup. For the 1999 collection, Trump took on a bride of Frankenstein aesthetic with curls sprayed upward, bleached eyebrows, and pastel green and blue eye makeup. For the 1997 presentation, she had a vampy look (her dark makeup was very of-the-moment in the '90s) with a shiny plum lip and a smokey eye that extended above the eyebrow. Her hair was worn in a futuristic top-knot with face-framing strands. Would we call it one of Trump's best beauty moments? No, we wouldn't.