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 on Saturday, March 22. 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, “Looks better when she’s not dating Trump Jr [sic].” Another said, “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.

Despite differing opinions on her appearance, Guilfoyle’s night at Mar-a-Lago was one to remember. Between her glamorous look, her philanthropic recognition, and the star-studded guest list, she remained a central figure at the event.

The buzz surrounding her presence only added to the attention that the gala received, ensuring its place as a talked-about occasion.