Some people look at the presidential advisor and see the family hood ornament; a woman who has overstepped her bounds being the only First Daughter in American history to ever have a West Wing office; perhaps even performing duties usually expected of the First Lady. Others see an entitled New Yorker now making the rounds of Washington D.C.'s elite circles. Others just see a wife and mother who made the best (and most) of the situation she was born into.
Regardless of one's POV, this is the middle child of Ivana and Donald Trump as she is now: a 38-year-old woman, a real estate executive, the better half to media scion Jared Kushner (whose brother, Joshua, is married to model Karlie Kloss), and political public figure speaking behind podiums to world leaders.
But what about back then? For all who never followed the NYC social scene, the veneer that says charmed life perhaps is not all that enviable, maybe even a bit sad and a little off-putting.
15 She Learned Of Her Parents' Divorce From The Tabloids
In the early 1990s, her dad had an affair with 26-year-old Miss Hawaiin Tropic, Marla Maples. Before her parents could break the news, Ivanka saw a newspaper headline trumpeting the divorce, and reporters swarmed her school for the 8-year-old's reaction. "No matter how [our parents] tried to relieve our anxiety and fears, the media undercut that.”
14 She Went To A Private Girls School
What a shock. If you watched Gossip Girl you already have an idea of what the exclusive Chapin School was like. Word has it that she was asked to leave at age 15 because of excessive absences due to her burgeoning modeling career. She kept flying to Mar-a-largo in Florida to shoot fashion photos for her portfolio.
13 Then Boarding School
She referred to the elite Choate Rosemary in Connecticut as "prison-like." Even though classmates described her as "quiet and shy," she stuck out as "new money" in an "old money" environment. The teen tried to fit in by wearing fleece and flannel, yet still sported a Prada bag, had a cell phone before they were ubiquitous, and a car.
12 Then Onto The Ivy League
The class of 2000 high school grad first matriculated at prestigious Georgetown University, then two years later transferred to her father's alma mater the University of Pennsylvania (founded by Benjamin Franklin in 1740) from which she graduated cum laud in 2004 with a bachelor's degree from the world-renowned Wharton Business School.
11 She Was A Teen Model
Guess who led the way for Kendall, Kaia, and Gigi and every other celebrity-daughter- turned-fashion-model? For several years in the late 1990s, the young one-percenter traveled the world walking in shows for the likes of Vivienne Westwood and Thierry Mugler, as well as gracing the cover of fashion glossies.
10 She Flew Coach
On a trip with her mom and brothers, the matriarch made herself comfy in First Class, while the teen celebutante and the boys flew back in coach because mom said they "hadn't earned it." As a little girl, her father fronted her the money to set up a lemonade stand, but she had to pay him back putting the pressure on her to turn a profit.
9 She Had A Kurt Cobain Phase
In her 2017 memoir Raising Trump, Ivanka reminisces about what she describes as her “punk phase,” detailing her love of Nirvana, hence smelling like teen spirit in a wardrobe of flannel shirts, and a questionable decision to dye her hair blue, which her mother made her re-dye blonde with a box of drug store hair color.
8 She Dated High Society
Her dad wanted her to end up with Tom Brady, but her taste seemed to lean in a different direction. Her pre-Jared boyfriends included a college student who's now an investment banker, a New York scion like herself named Bingo, Lance Armstrong, Topher Grace, Pierce Brosnan's son, and the heir to the Dole fruit fortune. Did you expect a plumber?
7 She Went Camping Alone
In an effort to prove she wasn't as soft and prim as was the image of the Upper East Side princess, the single New York gal, took two solo trips: hiking in Chile and then trekking through Patagonia, each for two weeks at a time, armed with a backpack and a tent which she pitched herself and not seeing another person.
6 She's Athletic
According to her mother, the overscheduled child did every after school class one can imagine: "Ivanka went for ballet lessons, painting, and piano classes" to name a few, but because her mother was an alternate on the 1972 Czechoslovak Olympic ski team that is what she learned and excelled at, fully participating in customary and competitive family ski trips.
