Tiffany Trump's Stunning Style Transformation

Tiffany Trump is arguably among the most stylish of Donald Trump's children. Much like her half-sister, Ivanka Trump (who's sported multiple outfits that cost more than the average rent), Tiffany's passion for fashion has been obvious in decades worth of sometimes safe, sometimes daring designer ensembles. But Tiffany isn't just a clothes horse. Despite becoming friendly with a number of big-name designers, she's still blazed her own trail.

"I have to emphasize that Tiffany chooses her own style, rather than Taoray Wang," her friend and designer Taoray Wang told South China Morning Post in 2017. "Tiffany is the kind of a woman who knows what she wants, and is never afraid to express herself," she added. Tiffany proved that when she put the spotlight on Wang by wearing a stunning, white, double-breasted coat from Wang's line to her dad's first inauguration. "She never said to me she is going to wear it that big day. But she did, and showed her admirable elegance and sophistication again with a Taoray Wang," she said. And she wasn't wrong. Tiffany has literally grown up before our eyes, and her stunning style transformation has included some gorgeous looks that took her from cute little girl to a sophisticated woman.

When you're the young daughter of a multi-millionaire business tycoon, chances are you're going to have a pretty impressive wardrobe, and that rang true for Tiffany Trump. The youngster showed her fashion flair early when she was snapped dressed to the nines at several events in 1997. During one, at Donald Trump's notorious Mar-a-Lago resort, Tiffany looked super cute in a red velvet babydoll dress with gold ribbon detailing and small pink flowers. She was also snapped at the Florida compound that year with her mom, Marla Maples, in a ballerina-esque, white satin skater dress with white hosiery and metallic gold Mary Janes.

The adorable dresses were just a taste of the fashionista Tiffany was destined to be. She went on to evolve the super feminine aesthetic her parents chose for her as a child, carving out own chic style in a way that fit the woman she was becoming.

As Tiffany Trump got older, she was all about the trends. During a trip to London in 2014, she was snapped at a restaurant wearing patchwork skinny jeans (which were super popular at the time) with pumps. She added a gold sequin jacket, which tapped into the metallic trend, and carried a trendy quilted bag.

Tiffany also proved she was paying attention to what was hot at Refinery29's Country Club Launch Event. Matching sets were also popular in 2014 and she nailed that look too, proving monochrome dressing isn't just for lazy days in an all-black crop top with high-waisted pants. The ensemble demonstrated how Tiffany was becoming bolder with her wardrobe choices as she neared her 21st birthday, flashing a sliver of her midriff. But the beauty wasn't 100% up to date, as her chunky, platform shoes were on the way out.

Tiffany Trump attended New York Fashion Week in 2017, where she rubbed shoulders with designers and even gave her own style commentary to The Cut when she attended Phillipp Plein's show. "He always has a way to incorporate himself and do what he wants to do, and doesn't succumb to the typical guidelines of what he should do," she said. But, unfortunately, her new fashion connections didn't shield her from a clothing fail. She wore a short LBD by Plein to his show, which featured silver and black rhinestones around her legs over a sheer mesh. Tiffany's outfit just didn't work and looked too tacky for a member of the president's family.

But she redeemed herself after her rare misstep. The beauty also supported Taoray Wang during Fashion Week, attending her show with Marla Maples. Tiffany was every inch a star in a form-fitting white dress with glittery slingback heels and a structured nude and light pink coat draped over her shoulders.

Tiffany Trump combined sophistication and femininity as she settled into life under an intense spotlight. Around 2020, she developed a penchant for pantsuits, ditching her signature dresses for colorful two-pieces to create a flirty corporate aesthetic. That summer, she opted for pale blue flared pants and a matching, fitted blazer set as she spoke to Donald Trump's supporters at the Republican National Convention. Three months later, she shared photos on Instagram in a similar suit, only that time she was a lady in red in a vibrant monochrome two-piece and matching square neck top.

Her newfound clothing confidence continued to develop over the next few years, as she strayed from conservative looks to try bolder outfits. In 2024, Tiffany was effortlessly stylish during a trip to Switzerland. In an Instagram snap, she stayed cozy in a modern, cropped sweater with trumpet sleeves but paired it with unexpected leather-look pants and vintage-esque round sunglasses for an edgy twist on a classic unlike anything we'd seen from her before.

In October 2024, Tiffany Trump confirmed she was expecting her first child with her husband, Michael Boulos. The big life change saw her adapt her new, edgier style to dress her growing bump with elegance and sophistication — plus a fashion-forward twist, of course. In January 2025, Tiffany attended Donald Trump's second inauguration in a classy, navy, velvet belted coat. Underneath, she added a matching collared shirt with a metallic button at the neck, which put her far away from the inauguration's worst dressed list.

A few days later, Tiffany took a big risk that paid off. In an Instagram upload, the mom-to-be stayed warm in a deep red coat that featured a high-fashion cape. Proving she'd come a long way since her patchwork jeans at fancy restaurant days, she paired the structured outerwear with bicep high, black, leather-look gloves, and matching patent boots. "This is the LOOK," one fan commented on her upload alongside a heart eye emoji. "The outfit! just wow!" another wrote. If her pregnancy wardrobe is anything to go by, her ensembles as she enters her mom era are sure to be a sight to behold.