Kimberly Guilfoyle Posts Very Busty Throwback Pic With Mom Of Barron's 'Best Friend'
Since breaking up with Donald Trump Jr., Kimberly Guilfoyle has rocked several revealing dresses while still remaining within the Trump family circle. On January 28, Guilfoyle posted a birthday shoutout to Dr. Gina Gentry Loudon on her Instagram Stories. The post included a photo of Gina and the Rumble media personality, who sported a lavender and white floral-print dress that featured a frilled skirt and plunging sweetheart neckline that put her assets on display. The photo was a throwback from March 2023, when the birthday girl uploaded an Instagram carousel after hosting multiple fundraisers. "Thank you to ... the Trump family for always generously giving of their homes, their time, and their love!" she wrote in the caption. The birthday shoutout appeared to be a ploy by Guilfoyle to remain relevant within the Trump family circle.
Gina has a strong connection to the Trumps — her son is Bo Loudon, who is the self-proclaimed best friend of Barron Trump. Bo is the opposite of Barron, as he prefers to keep a high public profile and is a budding right-wing influencer with a sizeable Instagram following. It likely is not a coincidence that Guilfoyle wanted to post a pic with the mom of Barron's friend, as the former Fox News anchor has been mingling with the Trumps at every opportunity.
Just over a week before the birthday post, Guilfoyle attended Donald Trump's inauguration. A source claimed that she used the occasion to keep tabs on her ex. "Kim is still very fond of Don, and kept a watchful eye out," the insider told People on January 23. Not only was she clocking Junior, but Guilfoyle flaunted her curves in a busty dress.
How Kimberly Guilfoyle is vying for Donald Trump Jr.'s attention
Kimberly Guilfoyle used the inauguration festivities to showcase several busty looks. Perhaps her most revealing outfit was at the Hispanic Inaugural Ball on January 20 — an event that both Donald Trump Jr. and his new girlfriend Bettina Anderson also attended. Guilfoyle wore another floral dress, and it also had an eye-catching plunging neckline that showed off her curves.
It wasn't the only risque inaugural look that Guilfoyle trotted out in front of her ex. For the Starlight Ball, she wore a low-cut blue dress that featured embroidered floral stitching. Par for the course, that number had a V-cut neckline that accentuated her assets. Guilfoyle must have been eager for attention, as she posted multiple snaps in the blue dress to her Instagram Stories — including one alongside Connor McGregor.
It seems that since splitting from Don Jr., Guilfoyle has leaned into wearing spicy outfits, which is semi-ironic considering that her dresses were reportedly a point of contention between the former couple. "Don Jr. has been telling people for months that Kim is so uptight and always dresses so professionally," a source told People in December 2024, shortly after their break up. "The tight dresses need to go and she has been told that," they added. Not only has she been using revealing dresses to get her ex's attention, but she also gave Trump a birthday shoutout. Guilfoyle took to her Instagram Stories on January 2 to upload a photo collage dedicated to her former fiance.