What Ivanka Trump Was Really Like In High School

Long before she was an adviser to the President of the United States, Ivanka Trump was just your average teenage daughter of a billionaire, attending an elite East Coast boarding school. Although the Trumps are not necessarily known for their modest taste, a teenaged Ivanka actually seemed pretty normal, as depicted in a feature in Seventeen magazine from more than 20 years ago.
In the late nineties, conspicuous consumption wasn’t really a thing for the teenagers in the largely white suburban enclaves of New England. We walked on the backs of our oversized corduroy pants, chewing up the hems and if you were lucky enough to have a Patagonia fleece vest, it wasn’t unusual for it to be puckered here and there with cigarette burns. We probably thought we didn’t “care” about the way things looked, but really we didn’t understand the value of our clothing. Most had never gone without — without food, without security, without a steady supply of mail order fashion from J Crew, and LL Bean and everywhere else I was sure “rich kids” got regular delivery from.
And at Choate, I’m told, Ivanka was not much different. Boarding school in a small Connecticut town meant a carefully cultivated uniform of low-key but high end sweatpants, wool cardigans, and hiking boots. To be flashy would have been to expose yourself as different, and different was the very last thing any of the Choate students wanted to be. This was a place Ivanka could fit in. There were scholarship students for sure, but most everyone was wealthy and a lot of kids were VERY wealthy (Carl Icahn’s daughter was there the same time as Ivanka) and flaunting that would be tacky. Better to dress like at any moment you might be spending a few hours in the parking lot of a Dave Matthews concert or as if you were on your way from Spanish class to lacrosse practice (which you were).
The January 1998 piece, first reposted by the Instagram account @thankyouatoosa, run by Casey Lewis, profiles a 16-year-old Ivanka in her dorm room at Choate Rosemary Hall in Connecticut, which she shared with two other girls. "Some people might be surprised I'm a normal teenager," Ivanka, who is pictured striking a very '90s cool-girl pose on a small wooden chair, told the magazine. The 15-by-11 feet room is normal: Her wall is adorned with string lights, photographs of friends and family, and a poster of Marilyn Monroe's iconic skirt-flying-up photo. "There's a lot of random themes from movies," she said. There's a black-and-white Robert Doisneau poster, which she purchased on the street in France, above her bed.
Still, according to a classmate, while Ivanka’s clothes were mostly fleece and flannel, there were things about her that stood out. Ivanka had one of the original black, box-shaped Prada bags that would serve as an inspiration for Kate Spade and become so ubiquitous. Ivanka was nice. She had plenty of friends. She was a regular teenager, but still it seemed she believed she was exceptional. As in, an exception to the rules. She had a cell phone at a time when only movie stars had cell phones. And she had a car on campus, something literally no other student had. She and her parents had apparently argued that it was necessary for her to have the car because in addition to being a student at Choate, Ivanka also had a modeling career.
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Sometimes she would argue with her dad on the cell phone. He wanted her to go to Wharton, as he did. She wanted to go to Georgetown to be with her boyfriend. In the end, Ivanka would spend a year at Georgetown before transferring to her father’s alma mater. Also — in what was surely a source of soul crushing embarrassment to teenage Ivanka — her father showed up to graduation in limo, greeting other students and parents as if any of them actually cared that he was Donald Trump, which meant something very different than what it does now.
It’s an interesting note that one of the most prominent photos adorning the walls is one of an 11-year-old Ivanka and her dad, President Donald Trump. He has his arms protectively on her shoulders as they both look off in the same direction. "That was the first night I met my agent," Ivanka, who at the time was a part-time model, said of the photo. "She asked me to stop by the agency in a few years." There's a mirror hanging on the wall, which Ivanka noted she has to "crouch" to see her face in since she's so tall.
And she made other concessions to her modeling career and her exceptionalism. Once after a holiday break, she returned to campus with a bruised and swollen face. For a week she wore her hair covering her face and told everyone she'd had her wisdom teeth removed. Whether this is a clue that Ivanka got cosmetic surgery in high school or she just had some severely impacted wisdom teeth is anyone’s guess, but the former would not be unusual for a rich prep school teen in the 90s — especially an exceptional one with a modeling career.
Although the room seems no different than that of any American teenage girl at the time, one can glean some insights into future Ivanka. Ivanka's image, much like a magazine spread, is perfectly curated. She grew up with unimaginable wealth, but her public persona (like her dorm) is that of a person who is almost implausibly down-to-earth. She wears immaculate designer clothes, but is never gaudy. She speaks with authority, but maintains a soft tone. She's an adviser to one of the most powerful — and divisive — men in the world, but still wants to be seen as relatable.
Ivanka, who grew up shuttling between multiple luxury residences, told Seventeen her unassuming dorm, with its austere furniture and plain, white walls, "probably expresses me best." It was a blank canvas, away from a demanding Dad, but in it she created a place where she blended seamlessly with the rest of the student body.
She added: "It's an atmosphere I created." But, it's more of a vacuum.

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