Vanessa Trump Has Totally Transformed Over The Years

Somehow, the world simultaneously knows a lot and very little about Vanessa Trump, despite her transforming before our eyes. Although much of her life has been lived in the public eye thanks to her ill-fated marriage to Donald "Don Jr." Trump Jr. ("Extra"'s cameras were on hand when he proposed), the former model has experienced quite the journey, having gone from being a single woman embedded in the New York party scene to a much quieter life in Florida with her five kids. "Vanessa is by nature is a very low-key person," a source told Page Six in 2018.

It makes sense, then, why interviews with Vanessa Trump have been few and far between since she ended her marriage to Don Jr. It's also understandable why her Instagram account mainly contains photos and videos of her eldest daughter Kai Trump showing her golf skills over private, at home moments. But while this elusive star — who Vanity Fair once dubbed "the most sensible Trump" — may now prefer to keep a low profile after years of soaking up the spotlight, there are multiple life events that have hit the headlines and shaped her into the woman she's become.

Vanessa Trump was born Vanessa Pergolizzi and lived a lavish life with her family (including her mom Bonnie Haydon, stepdad Charles Haydon, and sister Veronika Haydon) on New York's Upper East Side. The star likened her upbringing in the wealthy area to her then-future husband Donald Trump Jr.'s privileged childhood. "[We] were raised in high-profile families and learned the value of working hard and giving back," she told PoshCravings.com (via People).

But the upscale Manhattan town house wasn't the family's only residence. "While I was raised in the city, we always had a country home so you had the best of both worlds," Vanessa said. "I feel that it is a fantastic experience to grow up in a city with such culture and diversity." While growing up in the Big Apple, Vanessa got into modeling. Bonnie ran the modeling agency Kay Models and signed Vanessa up as a child.

Despite Vanessa Trump's privileged upbringing, she allegedly had a rebellious streak. Vanessa met Valentin Rivera in the fifth grade, who opened up to Page Six about growing up with the then future star. Rivera claimed he dated Trump in high school and was involved with criminal activity during their relationship. "[Vanessa] was worried in the beginning, but after I guess seeing the power of who I became, she was cool with it," he said. Vanessa's purported ex added, "She was fascinated. We were kids. She liked the street life at the time. She liked that type of environment — being around gang members and stuff." However, GQ reported Vanessa denied having a relationship with Rivera when later asked about it by Donald Trump Jr.

An anonymous former friend of Vanessa even told New York Magazine in 2018 of her supposed rough edges, "Now she's all dolled up and ladylike and s***, but she used to be this hard-rock in leather and baggy jeans. She was a total gangster b****." Another friend purported to GQ that Vanessa adopted a totally different look when she entered the spotlight. "She talked with an urban, gangster accent. She wore big hoop earrings, hair slicked back. She thought she was a gangster," they claimed. "She had a gangster boyfriend, and she acted like a gangster herself. She was somebody who went out of her way to intimidate people by having a scary boyfriend that could hurt people," they added.

Before taking on the Trump last name, Vanessa was called Vanessa Haydon, which was the surname of her stepdad, Charles Haydon. In the wake of her contract with Kay Models, Vanessa was snapped up by the world-famous agency Wilhemina Models and, considering she'd been practicing her runway walk since childhood, it's no surprise she saw a lot of success. The star's career allowed her travel internationally, as she attended fashion events and modeled across the globe, including in New York City and Sydney, Australia.

In 1997, Vanessa (who was a brunette at time) got her foot in the door as a businesswoman. The entrepreneur joined forces with her sister Veronika Haydon to open their own nightclub in Chelsea, New York, called Sessa. "It all puts you in Bali. I've never been there, but I'd like to go," Vanessa told WWD, referring to the club's exotic decor. Sessa would closed its doors in 2004 though amid several noise complaints and police callouts.

Vanessa was clearly running in the right circles as she lived the high life, as she was romantically linked to Leonardo Di Caprio in 1998. A source told Page Six at the time, "The couple could be seen holding hands, kissing and cuddling into the wee hours in a dimly lit corner." Valentin Rivera even accused publicly Vanessa of cheating on him with the "Catch Me If You Can" actor. However, a full-on romance didn't blossom between the two. In fact, an unnamed friend of Vanessa's denied she ever really dated Di Caprio and seemingly accused her of planting the story. "Vanessa played the media really well," they told New York.

Vanessa Trump's star power grew in the mid-2000s when she began expanding her empire via appearances on the big and small screen. She starred as an unnamed character in Jack Nicholson and the late Diane Keaton's rom-com "Something's Gotta Give." It seems her small acting role failed to set the world alight as the gig marked her first and last movie acting credit. Still, Trump continued to appear on TV screens as herself in the years that followed.

In 2004, she served as a celebrity judge at the "Miss USA" pageant. That was followed by appearances on the likes of the reality show "Bret Michaels: Life As I Know It" in 2010, and, the following year, on "The Oprah Winfrey Show." She also starred alongside her now former father-in-law Donald Trump on "The Apprentice USA."

In 2005, the woman then known as Vanessa Haydon officially got her famous last name. Vanessa (who was then a model with Next Model Management) married Donald Trump Jr. at the notorious Trump family estate Mar-a-Lago in front of a slew of famous names, including Joan Collins and Brittny Gastineau. The two followed up their nuptials by honeymooning in Mexico and Fiji. 

Vanessa was clearly loving living life in the spotlight at the time, as she brought "Extra" along to pick out her wedding dress. She and Don Jr. later invited the entertainment news show's cameras along to record the romantic outdoor ceremony too. And Vanessa was ready for a big family with her new husband. "She told me on her wedding night that she hoped to have five children," Vanessa's ex Elite Model Management agent Christine Schott told People.

The wedding came after the then happy couple met at a fashion show after being introduced (twice!) by Donald Trump. But they didn't keep in touch. Don Jr. told International Herald Tribune (via The Hollywood Reporter) that he and Vanessa then ran into one another for a third time at a birthday party a few weeks later, which is where sparks finally flew. Don Jr. later proposed to Vanessa in front of press and photographers inside a jewelry store at a New Jersey mall, which raised a few eyebrows as New York magazine speculated making the moment so public may have got him the ring for free.

Vanessa Trump and Donald Trump Jr. didn't waste too much time when it came to expanding their family. The newlyweds had big news to share in late 2006 when they told friends and family that they were expecting their first child together, their daughter Kai Trump, who was born the following year. Speaking to PoshCravings.com (via People), Vanessa opened up about her pregnancy and how she stayed healthy. "I worked with a trainer to maintain strength and to ensure a healthy pregnancy. I also tried not to do rigorous routines and to rest during the day," she explained. "Don and I cook a lot and always try to eat healthy, and now that Kai is here, we plan to keep that routine intact. I also have a post-pregnancy fitness trainer who I'm working with to get back in shape," she added. Vanessa also became a decidedly more glam version of herself as a fully fledged member of the Trump clan. Though Vanessa is stunning without makeup, she'd started wearing a little more and had dyed her hair blond. The star also opened up about her plans to raise her daughter in the Big Apple, but revealed she also wanted her to experience life outside the concrete jungle. Also in the native New Yorker's big plans? A return to her career. "I will go back to modeling and acting," she said. 

But Vanessa's focus seemed to be more on motherhood, as she didn't take on another movie role after "Something's Gotta Give." Instead, Vanessa and Don Jr. would go on to welcome four more children together. Donald Trump III was born in 2009, Tristan Milos was born in 2011, Spencer Trump was born in 2012, and they welcomed Chloe Trump in 2014.

In 2011, Vanessa Trump's career went in a new direction when she launched her own collection of handbags called La Poshett. This foray into fashion was publicly supported by her sister-in-law Ivanka Trump, who encouraged fans to check out the company's website and follow the brand on social media in a Facebook post. However, not everyone was so taken with Vanessa's collection. In the comments section for Ivanka's post, some viewers took issue with the price point. "Nice but waaaayyyyy over priced for the average person," one person wrote. Another commented, "Good for her but in my opinion WAY over priced." By 2018, La Poshett was no longer in business and there's little evidence the accessory venture ever left online.

That same year, Vanessa experienced a difficult time in her marriage. Though the claims wouldn't go public until a few years later, Donald Trump Jr. reportedly cheated on her with Danity Kane singer Aubrey O'Day after they met while filming "Celebrity Apprentice." A People source claimed Vanessa found out about her husband's apparent infidelity when she discovered flirty messages from the singer on his phone. A source purported to Page Six that Vanessa actually called O'Day to confront her. "Vanessa went gangster. Aubrey was shocked. Vanessa said some extremely unladylike things to her," they claimed. However, Don Jr. and the singer ended their supposed tryst after Vanessa found out and she seemingly forgave her husband's misdeeds. "Everything seemed to be patched after that as Vanessa had more kids afterwards," People's source noted.

Vanessa Trump's struggles continued around 2017 when her life changed drastically. She and Donald Trump Jr. were living in New York when Donald Trump won his first election and was sworn in as the 45th president of the United States. Vanessa's father-in-law's controversial move into politics meant the spotlight on the family increased significantly, and multiple reports claimed the mom-of-five struggled with the intensified attention. "She has [been] very stressed ever since the whole presidential election started. She didn't sign up for all of this. It's a life that is not easy to adjust to, especially with five kids," a source told Us Weekly. Page Six shared a similar story, with a source claiming, "She is uncomfortable with the attention her family is getting now the Trumps are on the world stage." The insider also noted Vanessa was particularly worried for her children amid the unwavering public scrutiny against the Trump family, with a People source claiming Vanessa told a friend, "[The security fears are] stifling."

However, on the surface, Vanessa Trump put on a brave face. She didn't say much publicly about her family's major lifestyle change, but attended her then father-in-law's inauguration and took to X to share photos of her children playing on the White House lawn. "We had a fun day visiting Grandpa and First Lady Melania at the White House!" she captioned it.

In 2018, Vanessa Trump and Donald Trump Jr. ended their marriage. The two confirmed the news to The New York Times in a joint statement. "After 12 years of marriage, we have decided to go our separate ways," they said. "We will always have tremendous respect for each other and our families. We have five beautiful children together and they remain our top priority," the former couple continued.

The announcement came amid rampant speculation there had been trouble in paradise between the two for a while, as Don Jr.'s reported affair with Aubrey O'Day going public. The day before the now former couple confirmed their breakup, a source told Page Six, "The problems have been there for a long time, the couple had hoped to stay together during the president's time in office, but it is getting harder to resolve their issues. He's never there." Another source told Page Six that Vanessa had supposedly grown unhappy with their financial situation and claimed Don Jr. oversaw all their money. "Vanessa has had to rely on her mother for financial help for her personal needs," they said.

Vanessa remained dedicated to her and Don Jr.'s five kids amid the upheaval though. "She'll do whatever it takes to make sure the kids are okay and not affected by this," an insider told Us Weekly. "She's been dropping the kids off at school every day still. Vanessa is a great mom and will do anything for her children," they added.

Despite once living a high-flying lifestyle in New York City full of nightclubs and runways (and later enjoying trips to the White House to see her in-laws), Vanessa Trump has embraced a more private lifestyle following her divorce, rarely making public appearances. Though she was once very active on X, as the years went on, her social media presence became more sparse. Previously, she regularly offered followers a behind-the-scenes look at her own life via family photos, but has since become seemingly more selective about the content she shares. Still, the star did share her holiday card for 2019 on X with her followers, as well as a shot of herself and her five children meeting Santa Claus. But, at the time of writing, she hasn't shared holiday snaps with all her kids since 2022.

Though she was clearly still spending time in New York with her kids in tow, Vanessa was also living her life in Florida. New York Post reported in 2021 that she'd been living in Jupiter in Palm Beach County and claimed Donald Trump Jr. and his then-partner Kimberly Guifoyle (who had multiple warning signs they were never going to last) had bought a property nearby.

After a few quieter years, Vanessa Trump had everyone talking in March 2025 when news broke that she was dating Tiger Woods, who lived around 30 minutes away from her in Florida. A source dished on their romance to Daily Mail, claiming they'd been quietly dating since Thanksgiving 2024. "She comes to his place on Jupiter Island. They're not living together. She comes over maybe a few nights a week. They just love hanging out, having dinner and schmoozing together," they said. Amid the gossip column chatter and signs Woods and Vanessa's relationship won't last, their romance became Instagram official with two loved-up photos. "Love is in the air and life is better with you by my side!" Woods captioned the images, in part. By late 2025, Daily Mail reported the two were still going strong. "It's gotten really, really serious," an insider said. 

At the time of writing, Vanessa is yet to feature her new man on her Instagram grid, though she'd clearly learned a lot about Woods' sport. Vanessa often shares photos and videos of daughter Kai Trump golfing as she pursues a golf career. "Congratulations on your first LPGA tournament! Watching you give it your all was inspiring," Vanessa captioned a slideshow of photos supporting Kai on the golf course. "This is just the beginning! I'm very proud of you," she added. 

It's clear that Vanessa has grown up a lot since her days partying and modeling in New York. Side by side pics prove how much, just like her fellow Trump women, she's physically transformed too. But it looks like her next chapter watching her kids grow up, living a quieter life, and falling back in love may be her most transformative era yet.