The Stunning Style Transformation Of Vanessa Trump

From his daughters, Ivanka Trump and Tiffany Trump, to his wife, Melania Trump, there are quite a few women who are making Donald Trump's life more interesting and way more stylish. One of them is also Vanessa Trump, the ex-wife of the former president's firstborn, Donald Trump Jr. While she hasn't been in the spotlight nearly as much as the aforementioned ladies, Vanessa has been a New York City socialite since the early aughts.

In fact, when Vanessa met the Trumps, she was working as a model; however, her dreams of becoming the next supermodel never came true. Of course, the story of a model becoming the daughter-in-law of a president is definitely intriguing enough for us to take a trip down Vanessa's fashion memory lane. From her stunning maternity looks (and with five kids, there were certainly plenty of baby-bump fashion moments) to toning her style down when Donald became president in 2016, Vanessa's style has certainly transformed over the years.

In the '90s and early aughts, 20-something-year-old Vanessa Haydon (originally Pergolizzi, prior to her mother remarrying Charles Haydon) was signed by Wilhelmina Models, and attending red carpets and entertainment industry events was not something she was a stranger to. At the time, we'd often see her together with her sister Veronika as the two beauties attended all the go-to socialite events in New York City.

Even though Y2K fashion (which had a major resurgence in 2024) was all about mismatched maximalism, Vanessa seemingly wasn't a big fan of that. Instead, she handpicked the trends of the early aughts that she liked, and she ditched the ones she didn't. Her style was youthful and fun, but at its essence, it was timeless and very simple. For dramatic occasions, she'd go for a silk gown in a bright color, and for a more casual look, she'd pair a white tank with a denim skirt. Her accessories were minimal — and if there was a statement piece, she'd always ensure not to overdo the rest of her look. As a model, Vanessa always looked put-together and pretty, and one thing we instantly noticed was that she rarely wore dramatic makeup. Instead, her skin was dewy, and her lips were glossy, serving that off-duty model look.

In 2004, Donald Trump Jr. proposed to Vanessa Haydon in front of a jewelry store that gifted him the $100,000 engagement ring in exchange for his public proposal photographed by the paparazzi. This undoubtedly catapulted Vanessa even higher in the world of New York City's elite. For The New York Times, she revealed that it was actually at a fashion show that the two had met. "I'm at this fashion show," she said in 2006. "Donald Trump comes up to me with his son: 'Hi, I'm Donald Trump. I wanted to introduce you to my son, Donald Trump Jr.'" Fast forward six weeks later, and their paths crossed again. "We talked for an hour," she admitted. And by the end of 2005, she swapped her last name for Trump's as the two tied the knot at a wedding ceremony in Palm Beach, Florida.

Between 2004 and 2005, a very subtle change could be noticed in Vanessa's style: The former model began favoring skintight and revealing pieces, often with a deep-V neckline that helped accentuate her incredible figure. One of her most memorable looks from the mid-2000s is undeniably the blue gown that featured a plunging bedazzled neckline, which she wore to a Fashion Group International event in 2005. Her style remained simple, but it certainly seemed as if Vanessa's newfound confidence allowed her to push her style out of her comfort zone even more. With the change in her fashion choices came a change in her hair color, too. Vanessa replaced her light-brown locks with a sun-kissed blond that seemingly gave her permission to play around with her look a lot more.

During the second half of the 2000s, Vanessa Trump became a staple at New York City fashion events, which she was often invited to. Her style steered even further away from the simplistic and neutral aesthetic she rocked prior to meeting Donald Trump Jr., as she was now embracing color for almost every outing. The silhouettes were always flowy and feminine, yet they never failed to accentuate her curves. 

By 2006, Vanessa and her husband were expecting their first child, which, of course, meant that she was giving us quite a few maternity looks. The model's style didn't change much throughout the pregnancy, as deep-V necklines and body-hugging silhouettes still remained common themes toward which she gravitated. Vanessa's hair stayed blond, too; however, instead of pin-straight, she was now more often rocking it in loose waves. Even though her fashion became more adventurous, the makeup she wore was still rather simple and minimal.

Soon after her first pregnancy, Vanessa Trump was once again a regular on red carpets, often accompanying her husband Donald Trump Jr. One thing we noticed by taking a look at her best fashion moments in 2008 is that motherhood absolutely hadn't changed the trajectory of her style as Vanessa decided to keep her fashion as fun and as eye-catching as possible. In fact, not many new moms would dare to rock the silver minidress with a bedazzled bustier, which Vanessa wore to the Operation Smile Gala in 2008 — and for that, we applaud her. Yes, she was now a mother, but she wasn't going to allow that to stifle her inner fashionista.

In 2008, Vanessa got pregnant again, and in early 2009, she welcomed the couple's second child. Just like throughout her first pregnancy, the model ensured her maternity looks remained fun and stylish, refusing to play into the narrative that pregnancy fashion is boring. One dramatic change that we did notice Vanessa went for was brown-ombré hair, which was much closer to her natural hair color.

At the beginning of the 2010s, Vanessa Trump was all about maxi gowns. The mother of two still kept her look youthful, but her style drastically changed from her early Y2K looks. For the 2010 Operation Smile Annual Gala, Vanessa decided to wear a stunning ombré blue gown, which she paired with statement jewelry — a chunky diamond necklace and dangly earrings — and a fun blue clutch. Even though the silhouette of the dress is timeless, it was the color choice that ensured this look was modern and fun.

In 2011, Vanessa was going through her third pregnancy, and this time around, she was a professional in maternity fashion. She and her baby bump attended another Operation Smile event in a glamorous black look that featured a cropped fur jacket, statement jewelry, and a funky animal-print clutch. In fact, we applaud her decision to incorporate animal print (which became the new "neutral" tone in 2023) into a glamorous outfit. While the former model had her brief moment with brown-ombré hair, as the 2010s kicked off she decided that being blond is her calling as she went back to her signature sun-kissed hair color.

Vanessa and Donald Trump Jr. welcomed their fourth child in 2012, and this time around, Vanessa's pregnancy was all about rocking bright and fun colors. Now in her mid-30s, Vanessa — who always exuded confidence — somehow seemed even more sure about her style choices. And while we love her shift toward bright colors, there is no denying that her confidence was what made her fashion choices stand out. Her fourth pregnancy came with more daring and bold looks, showing that Vanessa was enjoying having fun with her styling.

Now, remember the animal-print clutch Vanessa rocked to the 2011 Operation Smile event? We spotted her grabbing it quite a few more times between 2011 and 2012. The former model was clearly very fond of it, and we can't deny that it is indeed a perfect addition to a coral or blue dress. While most would opt for a classic choice like a black clutch, the animal print adds some very necessary texture to a monochromatic outfit.

While Vanessa remained loyal to her long blond locks, she did explore a bit more with her makeup, often going for a slightly more dramatic look than what we were used to seeing her wear. The lip color was just a tad more pink, the bronzer was more dramatic, and her eyes were often accentuated with eyeliner, eyeshadow, and even false lashes. Even though her makeup wasn't overly heavy, she certainly wasn't going for the no-makeup makeup look anymore. And we have to admit, her new makeup look definitely suited her colorful style.

We adored Vanessa Trump's maternity style during her fourth pregnancy, but for her fifth one, the former model decided to tone things down. Vanessa was pregnant during the first half of 2014, and most of the looks we've seen her in were pretty neutral and classic. Of course, her fashion choices were by no means bad; they were just rather bland and boring compared to what we were used to from the former model.

In June 2015, Donald Trump Sr. announced his run for president, and with that, Vanessa's style became even more simple and classic. Of course, having somebody from her family run for the highest and most influential position in the country was no joke, and Vanessa knew that the attention she was getting from the public thus far was nothing in comparison to what was coming. As if she wanted to play it safe and appeal to a wider crowd, she seemingly toned down the affinity for color and revealing cuts we've seen her rock in prior years. Now, Vanessa was all about looking the part of a soon-to-be president's daughter-in-law.

In 2016 and 2017, Vanessa Trump seemed as happy as ever. As a mother and a wife, she seemed to be thriving, and Donald Trump's daughter Ivanka Trump (who definitely fights her own battles with fashion) even gushed about her sister-in-law to People. "Vanessa is a machine," Ivanka said. "She can take all of [my children] and not even notice. She has five children and she's Wonder Woman to me. She can be taking care of them all simultaneously, each pulling on her and have direct meaningful connections with each of them at one time. It's remarkable."

During the first half of Donald Trump's presidential term, Vanessa and her husband were frequently seen supporting him. And just like in the two years before, Vanessa's style continued to be classy and professional. For the 2016 White House Correspondents' Association Dinner, Vanessa rocked a sleek floor-length white bandeau dress that exuded simplicity and sophistication. On Inauguration Day in 2017, she decided to go with a black dress and a burgundy coat over, showcasing that she could absolutely adapt her fashion to the family's new role. The only unexpected change during this period was that Vanessa decided to go even lighter with her hair, almost entering the sphere of platinum blond.

2018 was a whirlwind of a year for Vanessa Trump, as she filed for divorce from Donald Trump Jr. in March. "She was interviewing divorce lawyers before [Trump's presidency]," an insider revealed to Page Six. "No one thought he'd win. He won and she decided to stay until his term is over. But she just couldn't stand it anymore." What may have been a decision in the making for a long time certainly shocked fans, especially as the parents of five always put on a happy face in public. In early 2019, Vanessa and Donald Trump Jr. revealed that their divorce was finalized. "We finalized our agreement at the end of last year," they said through a joint statement (via Page Six). "We are incredibly lucky to have five amazing children and are committed to raising them together. Our kids and their happiness will always be our first priority."

Getting a divorce with five children involved is undoubtedly very hard, and having to do it so publicly certainly put plenty of additional stress on the former model. Needless to say, fashion was the last of her concerns at the time. For her public appearances, Vanessa kept things simple and easy, often going for outfits that consisted of just a classic dress. The effects of what she was going through could also be seen in her beauty routine, as the now ex-Trump went back to what she knew and trusted the most: warm blond and minimal makeup. In hindsight, it definitely seems as if she stripped back to the basics in all aspects of her look. With the divorce being finalized in 2018, Vanessa slowly withdrew from the public, appearing in front of cameras only when necessary. And with only a couple of photographed moments in 2018 and 2019, it is difficult to assess whether her private style was still more colorful and fun.

By 2020, we were hopeful that we would get to see more of Vanessa Trump's original style, but around this time, it became evident that Vanessa — who was now in her early 40s — had decided to say farewell to having fun with fashion, at least in front of the cameras. "Vanessa is by nature a very low-key person, and she is uncomfortable with the attention her family is getting now the Trumps are on the world stage," an insider had previously told Page Six. Vanessa's early 2020s style definitely reflects this sentiment, as dressing up for the spotlight certainly didn't seem to interest her anymore.

One of the rare instances she was photographed during this period was at the funeral of Ivana Trump in July 2022, which she attended with her ex-husband and their children. Dressed in a navy dress and black blazer, Vanessa paid her final respects to Donald Trump's ex-wife, and the mother of her ex-husband.

When Donald Trump announced he was running for president in the 2024 election, Vanessa Trump began appearing more in public to support him. Even though she was divorced from Donald Trump Jr., it certainly seems as if the two managed to remain friendly in order to co-parent their children. And for Vanessa, this meant that she remained a part of the Trump family, so supporting the Republican candidate by going to the Republican National Conventions in 2024 was a no-brainer.

At the Conventions, we got to see Vanessa wear mostly white outfits, which certainly accentuated her (some might say overly) tanned skin. The former model looked fresh and glowy, and even though she was now in the second half of her 40s, she certainly still resembled that model who was trying to have her breakthrough in the early aughts. In fact, were it not for the completely different style and the dramatic tan, we may have confused her for 20-something-year-old Vanessa Haydon. However, fashion-wise, she seemed to have toned down her looks even more, opting for overly simple ensembles like white-on-white jeans and T-shirts. By comparison, her Y2K fashion, with its bright colors and bedazzled details, was relatively boundary-pushing! 

Now, if you're hungry for more Trump family style, check out what Melania looks like nearly makeup-free (she doesn't let us see it often).