Ivanka Trump's Boldest Fashion Show Looks From Her Modeling Days

There are many ways to describe Ivanka Trump's wardrobe. Her looks are tailored to the nines and ultra-glamorous, with hints of fun and femininity still poking through her regal capes and Washington-ready sheath dresses. But long before she was the first daughter, a presidential advisor, or a household name, she was a model. Gracing runways in the late '90s for designers like Thierry Mugler and Jean-Charles de Castelbajac, Ivanka sported looks that we can't even reconcile with the refined aesthetic she's known for today.

"I just always was around [modeling] I guess," Ivanka revealed in a resurfaced YouTube clip from her runway days. "With my mom [former model Ivana Trump], and then my dad would have interviews and shoots, so I guess as I grew up, I kind of came accustomed to it." Being a professional even at the age of 16, Ivanka wore each look with poise.

The combination of '90s style (some of which seems alien by contemporary standards) and the avant-garde nature of high fashion created the perfect storm: a series of ensembles that can rival even Ivanka Trump's most head-turning looks of 2025. It wasn't just the daring outfits the designers put her in that have left us speechless, but also the big, loud, and boundary-pushing beauty styling, galaxies away from the so-called "Republican hair" and soft makeup we now associate with Ivanka. From pink hairspray and red face paint to thigh-high boots and metallic minis, these looks from Ivanka's modeling days left our jaws on the floor.

A decade after the original "Beetlejuice" was released, Ivanka Trump walked for Lolita Lempicka and seemed to take style cues from Michael Keaton's namesake character from the movie. The clothing here isn't overly shocking — we've seen worse than a pistachio-hued dress with metallic embroidery and an embellished coat with huge lapels, even though this was definitely an Ivanka Trump outfit that didn't impress. But we never thought we'd be seeing this hair, teased into an updo with tufts sprayed pink, on Ivanka. 

Ivanka Trump is almost unrecognizable with her natural hair color, and even more so in this look from a 1998 Jean-Charles de Castelbajac show, which was wild by her standards. Compared to some of the well-known runway makeup looks by legendary artist Pat McGrath, the single half-diamond outside her left eye is actually pretty tame, but something tells us we won't catch the first daughter in similar graphic makeup anytime soon. Now, the strapless, curtain-like dress, we could see her updating for 2025 since she loves a fringe moment.

In 1999, Ivanka Trump walked for Franck Sorbier, leading to a moment that would foreshadow a trend. The first daughter seems to be a fur fan, both when it comes to faux and the real deal, and has even gotten herself in trouble with PETA upon occasion. She's been seen in chinchilla coats, fur-trimmed outerwear, and even fur stoles, but it all began with what appears to be a fur-lined blazer with a plunging neckline, which she wore with short-shorts and sheer tights, which were popular in the '90s. The lived-in smokey eye makes messy glamorous here, but we're not quite sure what's going on with her hair.

The bleached-brow trend has come and gone over the years, reaching its height at the 2022 Met Gala. But over two decades before, Ivanka Trump achieved a very out-there look partially due to this creative beauty move. While part of the Thierry Mugler Spring 1999 Ready To Wear Collection show, she joined several other models in experimental looks. Along with the bleached brows, Ivanka wore graphic eye makeup with icy-blue and lime shadow, brought together with a wing and dramatic lower lashes. Even with the missing brows and the bold eyes, this look was taken to new heights, literally, with styling that looked like it was carried out by Edward Scissorhands.

We don't know for sure whether Ivanka Trump will ever return to modeling in a professional capacity, but we can say with 100% certainty that this was the last time we saw her in red thigh-high patent-leather boots — at least for now. The year was 1997, the show was Marc Bouwer, and Ivanka was put in head-to-toe fire-truck red. This look was finished with latex-looking gloves and earmuffs, so, at the very least, she would have been ready for winter. All that said, monochrome can be a good way to pull off your favorite over-the-knee boots.

Thierry Mugler, a frequent dresser of Kim Kardashian, is known for pushing fashion boundaries, so we're not surprised by this look. While walking in Mugler's "La Chimère" Haute Couture Parisian fashion show in 1997, Ivanka Trump rocked a furry look again, this time juxtaposed with shiny leather. But once more, it's the hair and makeup that made us do a double take to check whether this really is the same person who wore an Audrey Hepburn-inspired Givenchy ball gown to the 2025 inaugural ball. Grungy burgundy lips, smokey-green shadow, and a looped bedhead top knot certainly made for a head-turning look.

Having grown up in New York, Ivanka Trump nails Manhattan's Upper-East-Side aesthetic to the point where she fit right in as a one-time "Gossip Girl" guest star. But back in Marc Bouwer's Fall '98 show, she channeled the city in a different way: by looking like she was imitating the Statue of Liberty. Between the steel metallic tones, draping material on the bottom of the dress, and statuesque pose, it's difficult not to draw comparisons. Without the sheer navy sash at the hip, this dress would be a cute addition to Ivanka's current collection, though.