The Striking Style Transformation Of Ivanka Trump

Ivanka Trump was born with a brand name attached to a moniker that evokes affluence and grandeur. It also suits an heiress who grew up ensconced in a gauche imitation of the Palace of Versailles. Although Ivanka's parentage and self-indulgent surroundings seem like a recipe for an indolent nepo baby, she wasn't content to be a stylish socialite. That said, fashion has figured heavily into her life story. Her style has also evolved dramatically over the years.

Ivanka inherited some physical traits from her mother, Czech-American model Ivana Trump, that made it possible for her to follow Ivana's chicly heeled footsteps into the fashion industry. Then there is Ivanka's well-heeled father, Donald Trump, who had the financial means to turn her into a fashion "It" girl, if that was the style of notoriety she wanted to pursue. In 2015, Ivanka's former friend Chelsea Clinton spoke to Vogue about her then-pal's disinterest in being this type of nepo baby. "There's nothing skin-deep about Ivanka, and I think that's a real tribute to her because certainly anyone as gorgeous as she is could have probably gone quite far being skin-deep," she said.

In "Raising Trump," the late Ivana also insists that there's more to her daughter than meets the eye. "People think she's all hard polish and elegance, a control freak and a little princess, but really, she's down-to-earth, empathetic, insightful, and vulnerable at times," she writes. However, Ivanka's style journey did start with some princess-y attire.

Ivanka Trump enjoyed a lavish lifestyle growing up, and she dressed the part of a privileged child surrounded by luxury. In many of the childhood throwbacks she has shared on Instagram, she's all decked out in frills and other trappings of a penthouse princess — she wore a lot of lace, stockings, bows, and bobby socks. In "Raising Trump," Ivana Trump also recalls her daughter being fond of one luxurious fabric. "Ivanka loved those velvet dresses," reads the caption underneath a photo of Ivanka wearing a blue velvet dress with a bib collar.

But by age 8, Ivanka's parents were taking her to fashion shows, and she was no longer dressing like a Victorian-era doll. According to The New York Times, Ivanka got her early style education at runway shows for designers including Todd Oldham and Calvin Klein. She joined her mom at the Chanel Haute Couture fashion show for the luxury label's fall/winter 1992-1993 collection. She wore a black and gold shift dress featuring a flashy Rococo-style pattern. It looked like it was inspired by the interior of her family's Trump Tower penthouse.

While she was exposed to the fashion industry's crème de la crème, one of young Ivanka's biggest style influences was her mother. "I can remember sitting on her dressing room floor before she went out," she told Romy & the Bunnies. "I was always playing with her jewelry and shoes, and she was made up to the nines."

After making her runway debut at age 16, Ivanka Trump became a controversial catwalk regular. While Donald Trump had a close professional relationship with Elite Modeling's president, Monica Pillard, Ivanka insisted that her signing with the modeling agency was unrelated to her famous last name. "People like me for me, not for who my parents are. It is about outer beauty," she told The New York Times. Nevertheless, some industry professionals didn't think the runway was the right fit for her, with one fashion magazine editor telling Spin, "If it wasn't for her dad, she would be at best a B-model trying really hard to get work in Miami." As it turns out, Ivanka wasn't exactly enamored with the fashion world, either. "Modeling was not an endgame for me," she told Marie Claire in 2007. "I didn't particularly enjoy the act of it."

Modeling got her out of boarding school and an opportunity to work with designers such as Thierry Mugler and Betsey Johnson. She also got to wear some wild outfits. For a 1999 Franck Sorbier fashion show, she was dressed like a caricature of a well-to-do woman in black stockings, shorts, and a blazer with a dramatic fur collar.

In her mom's memoir, Ivanka recalls being uncomfortable in her runway attire. It was a million miles from her personal style, which, at the time, was heavily influenced by Nirvana's grunge look. "My wardrobe consisted of ripped corduroy jeans and flannel shirts," she writes. She also confessed to The Wall Street Journal, "I dressed badly. But only in retrospect. At the time, I thought I was the epitome of cool."

In "Raising Trump," Ivanka Trump recalls going through a rebellious phase as a teenager and dyeing her hair blue. Her mother reacted by making her use — gasp! — drugstore hair dye to return her hair color to its original shade. By the 2000s, Ivanka had seemingly decided to stop experimenting with grunge and punk styles. Instead, she embraced some of the biggest mid-aughts fashion trends, such as the long, dressy top (or short dress) over flared jeans and heels.

Ivanka wore the above look to a 2004 screening of Stanley Kubrick's classic "Dr. Strangelove" at Soho House in NYC. While it's not the epitome of style now, her fashion sense was sufficient to get her a job offer at Vogue. She was finishing up her senior year at Wharton School of Finance when she let Vogue editor-in-chief Anna Wintour know that she wasn't interested. "I just wasn't willing to delay my dream of becoming a builder," Ivanka explains in her book "Women Who Work."

Surprisingly, Donald Trump wasn't as keen on Ivanka following him into the real estate biz after she got the job offer. "I always envisioned Ivanka in fashion, heading up Vogue," he told Forbes of his dream of his daughter becoming Wintour's successor.

Anna Wintour also invited Ivanka Trump to the Met Gala for the first time in 2004. Ivanka clearly missed the butterfly train that Mariah Carey was the conductor on in the late '90s, as her satin slip dress with butterfly-shaped lace panels looked like something the diva would have worn during that era. And according to Ivanka, her runway wear wasn't the only area of her style that needed some improvement.

In "Women Who Work," Ivanka reveals that she was taken aback by Donald Trump pushing her to accept the Vogue job offer. It made her worry that he lacked confidence in her ability to work alongside him, and her apprehension was reflected in her apparel. In preparation to join the Trump Organization, she took a job working for developer Bruce Ratner. Of her attire at the time, she told The New York Times, "I think for the first year I wore a black Theory suit." She compared her look to the female professional's go-to uniform of the '80s: the power suit.

This reluctance to break the mold with her workplace wardrobe carried over into her early days working alongside her father in 2005. "I tried to assimilate," she told Forbes. "I wore my hair in a bob. I wore a black pantsuit."

In 2007, Ivanka Trump dipped her toes into the fashion business by starting with accessories. She told The New York Times that she decided to launch her jewelry line when working on a real estate deal with someone who supplied gemstones to Tiffany & Co. In a later interview with Social Miami, she compared her baubles to the coveted pieces sold by Tiffany's, and she revealed that her favorite jewelry from her line was anything with diamonds and tassels.

Ivanka said her love of expensive accessories came from Ivana Trump, joking to Marie Claire that this is "much to the dismay of both my father and my boyfriends." She also divulged that what she was looking for in arm candy was someone like Christian Bale in "American Psycho" (Ivanka married Jared Kushner in 2009; the bride wore Vera Wang).

Starting a business unrelated to anything her dad was doing seemingly did wonders for Ivanka's confidence. "I've never been at a place in my life where I've felt, quite frankly, sexier and more comfortable with my body. ... Generally, my self-esteem on every level is probably at a peak," she told GQ in 2007. This was evident in the way she started dressing. For the launch of the Trump Soho Hotel that year, she wore a slate gray minidress with ruching that made it cling to her body and a hemline that skimmed her upper thighs. Of how her views on professional attire started shifting, she told Redbook, "I realized I could express my abilities just as well in a pink suit."

By the end of the aughts, Ivanka Trump was leaving many potential cross-promotional opportunities on the table. Thanks to her boardroom appearances on "The Apprentice," more women were of her, so it was high time for her to make bigger moves in the fashion space. She started in 2010 with the launch of her shoe line, which she skillfully promoted in a Harper's Bazaar interview by saying, "I haven't purchased a pair of shoes since I started my brand."

Trump held the first runway show for her eponymous clothing label two years later. "I really designed only things that I personally would love to wear," she told Teen Vogue while touting her wares. She also revealed, "My signature color of my brand has always been coral." However, when debuting her brand at Lord & Taylor, the button-down she wore was more of a cantaloupe hue. She paired it with white skinny jeans and metallic peep-toe heels. Ivanka was her own best promotional tool and could often be seen modeling apparel from her clothing line on social media. For one shoot, she also utilized the view at Trump World Tower.

Trump told Redbook that some of her favorite clothing items around that time were little white dresses and cardigans. Flats were also a must. "I'm always running up and down buildings or around 800-acre properties for work — you can't do that in heels or flip-flops!" she explained.

Ivanka Trump and Jared Kushner have three children. They welcomed their daughter, Arabella Kushner, in 2011, followed by sons Joseph Kushner and Theodore Kushner in 2013 and 2016, respectively. While pregnant with Joseph, Trump told The Wall Street Journal she wasn't a fan of clothing designed to be maternity wear. "[It] makes you look much more pregnant than non-maternity wear," she explained.

Trump discovered what worked best for her were blazers and loose blouses tucked into stretchy skirts. If the skirts showed a little leg, even better. "One of the areas you don't gain so much weight is your leg," she explained. She demonstrated this tip's effectiveness in an Instagram photo that shows her sitting on the couch with Arabella. However, she swapped the blazer for a denim jacket and the skirt for a black-and-white shift dress that broke one of her pregnancy style rules. "When you're getting big all over, you might not want to wear a brightly colored or patterned dress," she said.

As for how becoming a mom affected her fashion choices, Ivanka told Romy & the Bunnies there was only one change. "I often find myself being accessorized by Arabella these days," she said. "If you see me wearing a hot pink bow in my hair, that's the work of my little fashionista!"

By 2014, Ivanka Trump had become an aspirational figure for many women, including some celebrities. Future royal Meghan Markle positively gushed over Ivanka on her now-defunct website The Tig, describing her brand as having "every covetable thing one could imagine" (via the Daily Mail). By 2016, Ivanka could boast that her brand was bringing in $100 million annually. But apparently, this wasn't enough.

While Ivanka has worn some ridiculously expensive outfits over the years, to support her father at the 2016 Republican National Convention, she wore a $138 sheath dress. This could have been celebrated as a savvy political ploy to seem more relatable. However, there was one issue: the blush dress was from her clothing line. When she tweeted to encourage her followers to purchase the dress, she was soundly criticized for using a political event for personal gain. After Donald Trump won the presidency, she would become even more shameless in her attempts to profit from her dad's new position of power. 

One of Ivanka's biggest political scandals came shortly after Donald's victory when her company sent a promotional email about a $10,800 bracelet from her jewelry line that she had worn on "60 Minutes." In 2017, when she was serving as one of her father's advisers, The Wall Street Journal found that she toed the ethical line by wearing clothing and accessories from her brand for almost 70% of her public appearances. "Ivanka Trump is testing the boundaries on federal rules that bar government employees from using their position to promote brands that personally enrich them," said University of Virginia associate professor in presidential studies Guian McKee.

In July 2018, Ivanka Trump's fashion label shut down after several stores quit carrying it. However, some sources told CNN its closure was the result of ethics laws that limited Ivanka's involvement in the company. Ivanka offered a slightly different explanation to The Wall Street Journal, saying, "My focus for the foreseeable future will be the work I am doing here in Washington."

A few days after the announcement about her brand's demise, a beaming Ivanka was photographed wearing a red Sandro pantsuit with matching pumps. It's common for the women of the extended MAGA universe — think Kimberly Guilfoyle and Marjorie Taylor Greene — to wear Republican red, but Refinery29 noted that it wasn't a hue Ivanka seemed particularly fond of at the time. It's as if she used her attire to announce she was now 100% dedicated to politics and ready to leave her fashion career behind.

Dawnn Karen, a Fashion Institute of Technology professor who studies fashion psychology, believed Ivanka's vibrant color choice was strategic in another way. "She's usually in these rooms with men so to give her that reassurance, to give her that self-confidence, to give her that boost, wearing red ... it supercharges her to walk in and own it and step into that power," she explained.

Ivanka Trump's clothing took a turn for the clinical during the pandemic. According to The Guardian, when she resumed attending public events, she wore white outfits for almost two months straight. It was, for instance, the color she was wearing in a much-mocked social media photo of her holding up a can of Goya beans like a model in a '60s-era ad being pitched by Don Draper. She was even wearing a style popular around that time: a blouse with bishop sleeves.

Ivanka's tweet included the brand's slogan: "If it's Goya, it has to be good." In response, some experts slammed the former "Celebrity Apprentice" mentor, accusing her of violating ethics laws to promote the Goya brand after its CEO, Robert Unanue, publicly praised Donald Trump.

Other occasions when Ivanka wore white were to distribute supplies in Washington and to attend an American Workforce Policy Advisory Board meeting with her dad, where she showed up in a knee-length white dress with a slash of black on the front. The Guardian suggested Ivanka was trying to evoke cleanliness when many Americans were worried about germs. Or perhaps she wanted to channel the healthcare workers who were being celebrated while her dad was being blasted for his handling of the pandemic.

Ivanka Trump's legs became the focal point of many of her outfits after she stepped away from the political sphere. "I am choosing to prioritize my young children and the private life we are creating as a family. I do not plan to be involved in politics," she said in a 2022 statement (via NBC News). Free from the constraints of dressing to impress foreign dignitaries and political donors, Ivanka began to look more like a young socialite ready for a long night out. She wore a little red Magda Butrym dress for a Miami Grand Prix event at Carbone Beach and a midnight blue Clio Peppiatt minidress for another Miami outing with Jared Kushner.

Ivanka also resumed hanging out with some of her celebrity pals, opting for an ivory, sequined crop top and matching maxi skirt with a high slit for Kim Kardashian's 43rd birthday bash in October 2023. She turned up the loud luxury dial to 11, wearing a silver and gold Manish Malhotra gown that screamed decadence after jetting off to India to attend the extravagant three-day wedding of billionaire Anant Ambani and Radhika Merchant in March 2024. 

But Ivanka chose a controversial outfit for Donald Trump's 2024 victory rally: one with a political silhouette. Her clothing does seem to reflect what's going on with her life, so who knows? Her blue pantsuit could signal an eventual return to working in politics.