Tiffany Trump's Complete Style Transformation

Melania Trump's numerous great fashion moments over the years, Ivanka Trump's (now-shuttered) clothing and shoe brands, and her stepmother's experience as a model prior to marrying her famous husband, have easily made them the most prominent members of the Trump family when it comes to style. But there's actually a third fashion girlie in the family: Tiffany Trump. The only daughter of Donald Trump and his second wife Marla Maples, Tiffany shied away from the limelight for much of her life — until her father's presidential campaign thrust her into the public eye, that is. Still, her reputation as the so-called "forgotten daughter" persisted due to Tiffany's comparatively smaller role in her dad's campaign and subsequent presidency, so the proud college grad's style was never as widely covered as that of Ivanka and Melania.

However, over the years, Tiffany has been slowly but surely developing her fashion know-how and finding her own sense of style. Having been raised by a mother who worked extensively as both a model and actor, she was likely exposed to all kinds of fancy clothing and shoe brands growing up, igniting an interest in fashion that continued to grow during her adult years. Tiffany got to learn more about the ins and outs of the fashion industry by working as an intern for Vogue in 2011 — an opportunity she landed with the help of Ivanka — before following in her mom's footsteps and making her runway debut at New York Fashion Week just five years later.

While she didn't end up pursuing a career in either fashion or modeling, focusing on getting her degree from Georgetown Law School instead, she frequently attends fashion shows and supports her favorite designers, all while blossoming into a bonafide fashionista in her own right. Suffice it to say that Tiffany Trump's style has had a truly stunning transformation.

Based on the small amount of public appearances she made with her mother as a child, Tiffany Trump clearly took style cues from Marla Maples. The adorable duo both sported straight-leg jeans and strappy sandals for the 2004 premiere of "Little Black Book" in New York City, though Maples paired hers with a sheer top while Tiffany opted for a striped blouse that was more appropriate for a then-11-year-old. They also wore similar jacket-and-pants outfits for a pre-Golden Globe awards style retreat and twinned in T-shirts, jackets, bootcut jeans, boots, and scarves for an outing in NYC, both in 2006.

While there was no clear sign yet of the style star Tiffany would grow up to be, her outfits were a reflection of her simple upbringing and her close bond with Maples, who raised her daughter by herself in California following the model's divorce from Donald Trump in 1999. "We were always together. She gave me the chance to have a normal childhood," Tiffany gushed in a joint 2016 interview with People, of her sweet relationship with Maples.

Tiffany Trump's teenage years brought forth a new chapter in her fashion journey, and it was likely entitled, "Out with the Jeans and in with the LBDs." At least, when it came to red carpet events anyway. Beginning in 2008, when she was 15, Tiffany began rocking little black dresses for most of her major appearances, such as the 2008 premiere of "The Hottie & The Nottie," starring Paris Hilton, and the Young Hollywood Awards in 2010. But though the teenager was often seen in these safe choices during this period, her style did evolve bit by bit as Tiffany grew up. 

For instance, she donned a simple style ideal for an 18-year-old for a "Love, Loss & What I Wore" event in 2011 but went for an elegant sleeveless design with a slit while attending the 2nd Annual Millennial Ball 2.0 two years later. Tiffany's hair and makeup also went through a visible upgrade. Up until 2011, she'd sported the same hairdo and glam for most appearances: Long, straight locks with a side part and side-swept bangs paired with peachy-toned makeup with heavily lined eyes. But once she turned 20, Tiffany finally switched things up and began appearing on red carpets with a middle part, bouncy blowouts, soft waves, and red lipstick.

The year 2017 was a significant one for the Trump family. Patriarch Donald Trump was sworn in and took office as the 45th president, which marked the start of what would become a yearslong obsession with the controversial leader and his family. And, for Tiffany Trump, 2017 was a breakout year for her style-wise too. By January, the then-23-year-old had already interned for Vogue and tried her hand at modeling but still had nobody to help her prepare for her father's inauguration and other events she would now be attending as a prominent first daughter. Enter Phillip Bloch, celebrity stylist and a close pal of her mom, who began working with Tiffany, telling CNN that his "goal is to make her a style star."

While she wasn't promoted to fashion icon status immediately, Tiffany scored several style hits, including the cream-colored gown embellished with crystal detailing that she wore to the candlelight dinner on the eve of Donald's inauguration and the edgy blue and black look (pictured above) that she rocked to a Philipp Plein fashion show that same February. Tiffany also looked effortlessly elegant in a white dress and light pink coat when she took in the runway show of one of her favorite designers, Taoray Wang, at New York Fashion Week, while her tweed jacket and LBD at a Just Drew event just screamed Blair Waldorf. 

However, a number of Tiffany's other outfits missed the mark or were just straight up inappropriate, such as the super short minidress with cutouts on the sleeves that she donned for a Philipp Plein runway show that September. Thus, Tiffany still had a long way to go before she and Bloch achieved his goal.

During the 2020 Republican National Convention, Tiffany Trump delivered an address in support of her father's reelection campaign. At that point, she already had four years of experience dressing for the part of first daughter, and it certainly showed. Tiffany looked radiant in a powder blue pantsuit featuring a double-breasted jacket and bell-bottomed pants that had a fun, dark blue twist in the pleats. She paired the suit with a rhinestone-covered top that complemented her glow-y, glossy glam. What elevated the look even further was Tiffany's visible confidence as she listed the many reasons why she believed Donald Trump should be voted back into the White House.

While he ultimately lost to Joe Biden, the divisive politician's youngest daughter won in the fashion department when she donned a powder blue peplum top and matching skirt for the 2020 State of the Union address and rocked an elegant pearl-studded jumpsuit to a White House event the following September. 

All of these super chic outfits proved how far she'd come from the mismatched bodycon dress and blazer combo as well as the confusing layered coat look that Tiffany wore during the early days of her dad's campaign and even his presidency too.

Tiffany Trump welcomed 2024 with a bang by posting a stunning photo of herself on Instagram. She showed off her figure in a backless, halter-neck silk gown. It was perhaps the most glamorous Tiffany had ever looked, save for her wedding — where she wore not one but three gorgeous gowns. Just a few weeks before that post, the Georgetown grad reminded followers again about some of the incredible looks she wore when Tiffany tied the knot with her billionaire heir husband, Michael Boulos, in November 2022, by sharing some throwback photos to celebrate their first wedding anniversary. Tiffany notably got married in a sparkly Elie Saab piece featuring long sleeves and a square neckline and later changed into a body-hugging satin gown by the same designer for the reception.

The proud first daughter had made just a few public appearances at the time and rarely posted on social media for much of 2024, but for the handful of looks we got from her, she kept it safe and simple, such as her two white outfits for the 2024 Republican National Convention, likely because Tiffany's appearances were mostly related to her dad's third presidential run. But Tiffany slayed the non-campaign outfit she showed off on her Instagram Stories in October 2024: A tiny black strapless dress with a flared skirt and a pair of stunning pumps. It was unclear when exactly the photo was taken, but it was shared just days after her father, Donald Trump, spoiled that Tiffany was pregnant with her and Boulos' first baby — possibly a signal that fans will soon be in for some interesting maternity looks.