The U.S. Ambassador to Greece and former prosecutor made a bold entrance at a high-profile event, sparking flurries of reactions and speculation online.
Kimberly Guilfoyle turned heads at the 2025 Wags to Riches Gala, held at Mar-a-Lago Club on Saturday, March 22. The event was organized by Furry Friends, a not-for-profit organization based in Jupiter, Florida, dedicated to rescuing, rehabilitating, and re-homing homeless animals.
The television personality and former fiancée of Donald Trump Jr. made a striking appearance in a dramatic black gown, capturing attention both at the event and on social media.
Guilfoyle, 56, arrived at the high-profile charity event wearing a floor-length black gown that accentuated her figure. The dress featured a plunging neckline with sheer lace details, offering a glimpse of skin.
Its voluminous skirt was covered in black feathers, adding to the dramatic effect. She accessorized with a bold statement necklace that drew attention to the dress’s neckline.
Her long brunette hair was styled in soft waves cascading over her shoulders. She looked confident as she mingled with other guests, appearing to enjoy the evening’s festivities.
A video shared by fashion designer Oscar Lopez on March 24 showcased the luxurious event, highlighting the decor, the guests, and Guilfoyle herself. The clip captured moments of her socializing and dancing, reinforcing the lively atmosphere of the evening.
During the event, Guilfoyle was honored with the CIGO award for her contributions to animal rescue efforts. Investigative journalist Laura Loomer shared the moment on X, writing, “Congratulations to my friend @kimguilfoyle for receiving the CIGO award at the Furry Friends Animal Rescue Gala at Mar a Lago last night! Kimberly is a great defender and supporter of animals and does a lot to help and support local animal rescues in South Florida!”
A video included in Loomer’s post showed Guilfoyle accepting the award onstage and sharing a few words about her dedication to animal welfare.
The gala drew several well-known figures, including actor Kelsey Grammer. The actor, known for his role in “Frasier,” was dressed in a maroon-checkered tuxedo jacket over a white button-down shirt, pairing it with blue trousers and matching sneakers. His presence at the event added to the evening’s star-studded appeal.
Guilfoyle’s appearance at the gala quickly became a topic of discussion online, with many commenting on her new look. Some praised her, while others speculated about possible cosmetic procedures.
One person wrote, “She has a much softer look to her and she is gorgeous.” “I will say she looks much healthier, thank God. Being with Jr was going to kill her [sic],” another added.
One netizen asked, “I’m not a fan of Kim’s, but she sure looks better since her separation from Jr. Is that even her?” Another commented, “Best she’s ever looked.” “She got her face fixed!” someone else noted.
On Facebook, reactions were mixed, with some expressing skepticism about changes to her appearance. One person commented, “Yea she doesn’t look that great. She’s had way to much plastic surgery [sic].”
Another added, “She was beautiful before she had all that work done.” “Too much Botox and injections [sic],” wrote someone else.
Guilfoyle’s appearance at the gala came months after her split from Trump Jr., whom she dated for several years. The two were first linked in 2018, following his divorce from Vanessa Trump.
On May 9, 2018, Page Six reported that a source had revealed, “Don Jr. and Kimberly are seeing each other, and are having a great time. While he wants to respect the privacy of his family, he is getting divorced, and he enjoys Kimberly’s company.”
After dating for nearly three years, the couple got engaged on December 31, 2020 — Trump Jr.’s birthday. However, they kept the news private until January 2022.
That month, Daily Mail confirmed their engagement, citing a source who stated, “Don and Kim got engaged on New Year’s Eve 2020—which is Don’s birthday. They’ve been together for almost four years now and have been friends for 15 years.”
At the time, Guilfoyle shared her excitement in a heartfelt Instagram post on January 1, 2022, writing, “Tonight was extra special celebrating @donaldjtrumpjr’s birthday. Don, you are strong, smart, courageous, funny and the love of my life. I can’t wait to spend the rest of our lives together. Love you.”
She included photos from the celebration, featuring herself with Trump Jr. and Donald Trump, as well as a close-up of her engagement ring.
In late 2024, news broke that Guilfoyle and Trump Jr. had parted ways. Their breakup was confirmed by People on December 12, shortly after Trump Jr. was seen holding hands with Florida socialite Bettina Anderson.
At the time, a source cited by People stated, “It’s an amicable split. It’s not one that is going to blow up, at least at this point.”
Despite the breakup, Guilfoyle reportedly remains on good terms with the Trump family. The source further added, “The Trump family is still enamored with her. She’s very intelligent, very smart, very loyal. Even before she and Don were together, she was close with the family. She knew Donald before she knew Don Jr., and that connection is strong. So nothing has changed.”
However, the source also noted that Guilfoyle’s personality can be strong-willed, noting, “She’s not easy to deal with. She’s very direct, very matter of fact.”
Following her split from Trump Jr., Guilfoyle remained active in politics. On December 11, 2024, President Trump announced her appointment as the U.S. Ambassador to Greece in a post on Truth Social.
“Today, I am very pleased to announce the appointment of Kimberly Guilfoyle as the United States Ambassador to Greece. For many years, Kimberly has been a close friend and ally. Her extensive experience and leadership in law, media, and politics along with her sharp intellect make her supremely qualified to represent the United States, and safeguard its interests abroad,” wrote the 47th U.S. President.
“Kimberly is perfectly suited to foster strong bilateral relations with Greece, advancing our interests on issues ranging from defense cooperation to trade and economic innovation. Congratulations Kimberly!” concluded the POTUS.
Guilfoyle also acknowledged her appointment in her Instagram bio, where she includes the title, “Appointed by President Donald J. Trump as the U.S. Ambassador to Greece.”
Before stepping into the political arena, Guilfoyle was a well-known television host. She worked for Fox News for over a decade, serving as a co-host on “The Five.” However, in July 2018, Fox News confirmed her departure in a brief statement, “Fox News has parted ways with Kimberly Guilfoyle.”
Her exit was abrupt, with no farewell appearance on air. Reports at the time suggested that her relationship with Trump Jr. had created ethical concerns due to her frequent discussions about Donald Trump on the network.
Shortly after leaving Fox News, she joined Trump Jr. on the campaign trail for the 2018 midterm elections and later took on a role at America First Policies, a nonprofit supporting Trump’s agenda.
Guilfoyle’s appearance at the Wags to Riches Gala not only showcased her striking fashion choice but also highlighted her philanthropic efforts, political career, and ongoing public interest following her split from Donald Trump Jr.
As she takes on her new role as U.S. Ambassador to Greece, her influence in both social and political spheres remains a topic of discussion.
Meanwhile, her ex-fiancé Trump Jr. has moved on, sparking fresh speculation about his personal life. His new relationship with Bettina Anderson has drawn attention, with some insiders claiming she has a pattern of dating older, wealthy men.
