You Won’t Believe How Much Ivanka Trump Has Changed

With her buttery blonde hair, rosy-nude makeup, and Ballet Slippers manicure carefully calculated for her powerful, unelected White House position, it's hard to imagine a time when Ivanka Trump didn't look like, well, Ivanka Trump. In her two years now as an advisor to the President of the United States (slash dad), she's perfected her image as a glamorous yet professional government official — though her credentials and actual work in the White House still raise questions. As does the fact that her longtime makeup artist is a Mexican immigrant, in spite of the family's policies and demeaning rhetoric directed at the country.

But Ivanka wasn't always trying to craft such a political image. After her living her entire life in the spotlight, first appearing on red carpets when her age was still in the single digits, Ivanka has tried it all: messy updos, ultra-smoky eyes, and glitter lipgloss with eyeshadow to match. There was even a time when (*gasp*) she wasn't a blonde and loved a bright orange lip. And of course, who can forget her infamous "punk phase?"

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As she remains in the public eye, we're taking a look back at Ivanka's own beauty evolution — from the daughter of a businessman-turned-reality TV-star to a first daughter working in the White House — and what it all really means.

Photo: Ron Galella/WireImage.
1991

When you were 10 years old, your typical Tuesday nights were probably spent watching SpongeBob SquarePants and sneaking some Fruit Roll-Ups before dinner. But for Ivanka, hers involved going to galas at the Plaza Hotel. In her first real red carpet moment, Trump attends the Maybelline Awards in New York City — in Chanel, of course.

It's hard to tell if she's wearing a ton of blush, or if those Glossier-worthy rosy cheeks come courtesy of just being a 10-year-old. Honestly, we're interested in that tiny bag more than anything.
Photo: Mitchell Gerber/Corbis/VCG/Getty Images.
1993

Not even Ivanka Trump could dodge the inevitable braces stage of American adolescence. With her naturally straight hair now parted down the middle, the 11-year-old was already on-trend for 2018.
Photo: Ron Galella/WireImage.
1994

At 12 years old, Ivanka (or her parents) finally decided that she was ready for makeup. Here with her mother, Ivana Trump, and future stepfather Riccardo Mazzucchelli, Ivanka arrived at a charity benefit in very 1994 berry lipstick, a subtle hint of brown eyeliner, and one especially cool layered choker.
Photo: Ron Galella/WireImage.
1996

For her father's 50th birthday, Ivanka, now 14 years old, matched every other freshman high schooler with shimmery eyeshadow, a bit of lipgloss, and what appears to be either a fresh Florida tan or a few sweeps of bronzer on her cheeks.
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Photo: Mitchell Gerber/Corbis/VCG/Getty Images.
1997

When she was in her late teens, Ivanka began a short-lived career as a fashion model, walking on fashion runways across New York City. Here, at a Marc Bouwer show in 1997, the young Trump got the punk makeover of her dreams, with wild exaggerated red eyeliner, bright red lips, and red highlights in her teased hair. (When Ivanka tried to make this a permanent lifestyle by dyeing her hair blue, her mother intervened with a box of blonde Nice 'n Easy.)
Photo: Ron Galella/WireImage.
1998

Since that punk aesthetic wasn't a fit (for the family, not Ivanka), she channeled Old Hollywood glam for this Valentine's Day party in 1998. This also appears to be the first time Ivanka got ahold of tweezers; no one was immune to the thin brows of the decade.
Tony Barson Archive/WireImage
2001

After years of embracing her natural blonde color, Ivanka did a little risk-taking in 2001, dyeing her hair a light brown shade before a Red Cross gala in Monaco, which she attended alongside her mom.
Photo: Stephen Lovekin/FilmMagic.
2003

That brunette phase turned out to be just that — a phase — with Ivanka going back to her blonde roots quickly thereafter. For a film screening in New York in 2003, she tried a rare messy updo, and also experimented with heavier, darker eyeliner for a bit of an edgier look.
Photo: Dimitrios Kambouris/WireImage.
2004

Starting in 2004, Ivanka started to wear her hair in romantic curls, rocking this updo to the Met Gala that year. To match her champagne dress, she wore shimmery peach makeup on the apples of her cheeks, her eyes, and her lips. Matchy makeup had met its match.
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Photo: Michael Loccisano/FilmMagic.
2005

Behold: The one time Ivanka wore a short bob. At the 2005 Met Gala, she arrived in a choppy, short bob that hit just below her ears. In another (maybe future) life, this would fit a Fox & Friends hosting gig perfectly.
Photo: Chris Weeks/WireImage.
2006

For her 25th birthday party, Ivanka tried on a '60s look, pulling her voluminous hair back with a thick black feather headband — and finishing with quintessential cat eyes.
Photo: Patrick McMullan/Getty Images.
2007

Even though this image of Ivanka is from 2007, it really could pass for a picture taken, like, yesterday. This is when she started to craft a look of her own, with her hair styled sleek and straight alongside slightly flushed cheeks, a bit of light pink lipgloss, and just the slightest hint of eyeliner and mascara.
Photo: Andrew H. Walker/Getty Images.
2009

Channeling ballerina beauty at a gala at the Metropolitan Opera House in 2009, Ivanka wore her hair parted down the middle and pulled back into a low bun, with heavy black eyeliner and plenty of lashes for a dramatic effect.
Photo: Dimitrios Kambouris/FilmMagic.
2010

It was all about the glow for Ivanka at the 2010 Met Gala, which celebrated American women in fashion (which, at the time, included her). With her hair styled up in those romantic ringlets she loves, Ivanka kept the focus of her makeup on the eyes, with bronze eyeshadow and plenty of mascara.
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Photo: Peter Kramer/NBC/NBC NewsWire/Getty Images.
2012

A departure from her typical sleek, straight hair and curly updos, Ivanka tried messier waves on for size while promoting The Apprentice on The Today Show.
Photo: Rob Kim/FilmMagic.
2013

Ivanka put her own twist on retro beauty for the launch of her very own fragrance at Macy's in 2013, wearing her hair in Old Hollywood waves and a rare bright-orange lip.
Photo: Larry Busacca/Getty Images.
2014

Ivanka continued to play with lip colors into the next year, including at the 2014 Met Gala, which she attended with her husband, Jared Kushner. Her cherry red pout contrasted sharply with her green gown — but, let's be real, all eyes were really on that giant donut bun.
Photo: Debra L Rothenberg/FilmMagic.
2015

When not at Met Galas during this era, Ivanka mostly relied on her signature hair and makeup moves, like sculpted bronzed cheeks, a brown smoky eye, and slightly wavy hair pulled back into a loose bun.
Photo: Mark Reinstein/Corbis/Getty Images.
2016

By 2016, Ivanka Trump was now a political figure as she traveled around the country campaigning for her father, including here at the 2016 Republican National Convention. During this time, Ivanka tended to wear consistent hair and makeup looks — a calculated move she shares with her stepmother Melania.
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Photo: Win McNamee/Getty Images.
2017

Now officially a first child and advisor to the president, Ivanka stuck to her tried-and-true uniform in 2017, wearing long, straight hair parted down the middle, neutral makeup, and an everything-is-fine-we-swear smile.
Photo: Alex Wong/Getty Images.
2018

Trump's second year in the White House has seen her ever-so-slightly evolving her look, adding more styles like retro waves, loose buns, and extensions for extra volume. This year she's also had a bit more fun with makeup, easing into things like red lipstick, peach lipgloss, and a smokier eye. Compared to everything else going on at the White House, a little makeup experimentation seems relatively low risk.
Photo: Remo Casilli/REUTERS.
2019

After cutting her hair into a dramatic bob in early September, Trump arrived at the Misha Nonoo wedding in Rome — which had people like Meghan Markle and Katy Perry also in attendance — with her short hair styled in Grace Kelly-esque soft waves.

Though the bob may be a departure from her usual beauty profile, clearly Trump's still got a thing for a little retro flair.
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