If you only know Ivanka Trump as the polished political advisor or the boardroom presence on The Apprentice, seeing her mid-90s runway shots is kinda like finding out your quiet librarian used to play bass in a punk band. It’s jarring. The slicked-back hair, the experimental face paint, and the "too-cool-to-care" teenage pout are worlds away from the curated, soft-glam aesthetic she’s lived in for the last twenty years.
But those early photos aren't just a weird footnote. They were her job.
Most people assume she just walked into a room and was handed a cover because of her dad. Honestly, while the Trump name definitely opened the door—specifically the door to Elite Model Management—the industry in the late '90s was brutal. You can have the biggest name in the world, but if you can't walk a straight line in six-inch heels or look good under harsh fluorescent lights, you're out. Ivanka didn't just linger in the background; she was everywhere for a brief, intense window of time.
Why Ivanka Trump Modeling Photos Still Matter Today
It’s easy to dismiss these images as vintage curiosity. But look closer. These photos capture a specific era of New York fashion where "celebrity offspring" wasn't even a fully formed category yet. Long before Kendall Jenner or Kaia Gerber were household names, Ivanka was the blueprint for the "socialite-turned-model" phenomenon.
She started young. Really young.
At 14, she signed with Elite. By 15, she was on the cover of Seventeen (May 1997). If you find a copy of that issue, she’s wearing a striped shirt and looking like every other suburban teen, except her cheekbones were already doing most of the work. That cover was basically her "hello world" moment.
The Runway Reality
The runway was where things got weird. We’re talking about the 1990s, where designers like Thierry Mugler and Vivienne Westwood were pushing boundaries that would make today’s "quiet luxury" fans faint.
- Thierry Mugler (1998): She walked the Spring/Summer show with bleached eyebrows. Let that sink in. The woman we know for perfectly manicured brows once stood on a Parisian stage looking like a high-fashion alien with icy blue shadow and dramatic, spidery lashes.
- Marc Bouwer (1997): There’s a famous shot of her in head-to-toe fire-engine red. Patent leather boots that went up to her thighs, matching gloves, and even red earmuffs. It’s peak late-90s camp.
- Lolita Lempicka (1998): This one is a favorite for internet deep-dives. She had her hair teased into a massive, bird-nest updo with tufts of neon pink spray.
She wasn't just "playing" model. She was working the circuit. She did the New York, Paris, and Milan rounds, appearing for Paco Rabanne and Tommy Hilfiger.
The "Nepo Baby" Elephant in the Room
Let’s be real for a second. Would Ivanka have been at the top of the Elite board without Donald and Ivana? Probably not. Her mother, Ivana, was a model herself and knew the industry's power players. Her father had long-standing ties with John Casablancas, the founder of Elite.
But here’s the thing: the camera doesn’t care who your dad is.
In those 1997-1999 photos, you see a girl who was nearly 5'11" and had the "look" the industry craved at the time—something between a classic beauty and a moody teen. She once told Inside Edition back then that she didn't "need" to model because her family had money, but she did it because she loved it.
The Quick Exit
By the time she was 20, the modeling photos stopped appearing. The "modeling bubble," as she later called it, burst. She didn't just phase out; she seemingly ran away from it. In a 2007 interview with Marie Claire, she didn't hold back. She described models as "the meanest, cattiest, bitchiest girls on the planet."
She basically compared the fashion industry to real estate, saying both were ruthless, but she found the people in fashion to be "under-educated and pampered." It’s a sharp critique from someone who had been on the inside. She used the career to travel and see the world, then pivoted hard toward Wharton and the family business.
How to Find Authentic Archives
If you’re looking for these photos today, you have to be careful. The internet is full of AI-generated fakes or heavily filtered "reimagined" versions of her past. If you want the real deal, you’ve got to look at the agency archives or verified Getty collections.
- Search by Designer: Look for "Ivanka Trump Marc Bouwer 1997" or "Ivanka Trump Mugler 1999." These are the most documented shows.
- Editorial Credit: She did a lot of work for Elle and Glamour in that era. These shoots are far more "high fashion" than the paparazzi shots you see from her later years.
- The Seventeen Cover: This is the Holy Grail for collectors. It’s the most authentic look at her before the "Trump Organization" polish took over.
What These Photos Tell Us Now
Looking back at these images in 2026, they serve as a reminder that public personas are built, not born. There’s a version of Ivanka Trump in a box somewhere in a photographer's studio—one with pink hair and a Vivienne Westwood corset—that doesn't fit the narrative of the woman we see today.
It’s a lesson in brand management. She took the visibility of the runway and translated it into a business empire (her jewelry and clothing lines, which had their own massive run before closing in 2018).
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What to do next: If you’re researching her career for a project or just curious about 90s fashion, check out the digital archives of Vogue or Harper’s Bazaar. They often feature "Then and Now" retrospectives that include her early runway work alongside peers like Gisele Bündchen, who was starting out at the exact same time. It’s a wild trip down memory lane that proves just how much the fashion world has changed—and how much Ivanka has, too.