‘Is That Really Her?’: Donald Trump Jr.’s Ex-Fiancée Turns Heads at Wags to Riches Gala in Mar-a-Lago

| March 26, 2025 | Celebrity | No Comments

The U.S. Ambassador to Greece and former prosecutor made a striking entrance at a high-profile charity event—quickly sparking waves of online buzz and speculation.

Kimberly Guilfoyle stole the spotlight at the 2025 Wags to Riches Gala, held at the Mar-a-Lago Club on Saturday, March 22. Hosted by Furry Friends, a nonprofit based in Jupiter, Florida, the evening supported the rescue and rehabilitation of homeless animals.

A closeup shot of Kimberly Guilfoyle’s black dress from the Wags to Riches Gala, as seen in a video dated March 24, 2025 | Source: Instagram/realoscarlopez

The TV personality and former fiancée of Donald Trump Jr. turned heads in a glamorous black gown, drawing attention from both attendees and social media users.

At 56, Guilfoyle arrived at the event wearing a dramatic floor-length gown that hugged her figure. The design featured a plunging neckline with delicate lace, while black feathers adorned the skirt, creating a bold silhouette. A statement necklace added even more flair to her look.

Kimberly Guilfoyle is seen descending the staircase in a black dress at the Wags to Riches Gala, in a video shared on March 24, 2025 | Source: Instagram/realoscarlopez

Her signature brunette waves flowed over her shoulders, and she exuded confidence as she mingled with guests and took part in the evening’s celebrations.

Fashion designer Oscar Lopez shared a video from the gala on March 24, showcasing the luxe decor, the crowd, and Guilfoyle dancing and socializing—adding to the energy of the night.

During the event, she was presented with the CIGO award for her contributions to animal welfare. Journalist Laura Loomer captured 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 passionate defender of animals and supports many rescues throughout South Florida!”

A video clip showed Guilfoyle accepting the honor and briefly speaking about her dedication to the cause.

The gala also drew celebrities like actor Kelsey Grammer, who wore a maroon-checkered tuxedo jacket and added to the star-studded ambiance.

Still, it was Guilfoyle’s appearance that ignited the most conversation. Many fans commented on her new look—some in admiration, others questioning the changes.

Donald Trump Jr. high fives Kimberly Guilfoyle before speaking at the annual Conservative Political Action Conference (CPAC) at the Gaylord National Resort Hotel And Convention Center on March 3, 2023, in National Harbor, Maryland | Source: Getty Images

“She looks much softer and is absolutely stunning,” one user commented. Another added, “She seems healthier now—thank goodness. Being with Don Jr. was draining her.”

Kimberly Guilfoyle shares her thoughts alongside U.S. President Donald Trump during a Greek Independence Day celebration at the White House on March 24, 2025, in Washington, D.C. | Source: Getty Images

Others were more critical, with remarks such as, “Is that even her?” and “She doesn’t look the same. Way too much work done.”

Some expressed concern: “She was naturally beautiful before,” while another wrote, “Too much Botox and fillers.”

Her appearance comes just months after her split from Donald Trump Jr., with whom she had been engaged since 2020. Their breakup was confirmed in December 2024 after Don Jr. was spotted with socialite Bettina Anderson.

Despite the separation, insiders claim Guilfoyle remains close to the Trump family. “The family still adores her. She’s sharp, loyal, and was connected to them long before she dated Don Jr.,” a source shared. However, they also admitted she can be “strong-willed and direct.”

Soon after the breakup, Guilfoyle made headlines again—this time for her appointment by President Trump as the new U.S. Ambassador to Greece. Trump praised her legal and political experience in a Truth Social post, describing her as “perfectly suited” for the role and praising her intellect and dedication.

Guilfoyle now proudly includes the title “Appointed by President Donald J. Trump as the U.S. Ambassador to Greece” in her Instagram bio.

Before her political chapter, she was widely known for her career on Fox News, where she co-hosted The Five. In 2018, she abruptly departed the network and later joined the Trump campaign trail, taking on a leadership role at America First Policies.

Her presence at the Wags to Riches Gala signaled not just a fashion moment, but a new chapter—one that blends diplomacy, philanthropy, and continued public intrigue.

Donald Jr. and Vanessa Trump at the 102nd White House Correspondents’ Association Dinner on April 30, 2016, in Washington, D.C. | Source: Getty Images

And while Donald Trump Jr. has moved forward with Anderson, Kimberly Guilfoyle remains firmly in the spotlight—proving, once again, that she’s not just part of the narrative, but a force within it.

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