Kimberly Guilfoyle Confuses Charity Event For The Club In Gaudy Mini-Dress
Kimberly Guilfoyle is ready to put herself back on the market following her split from Donald Trump Jr., but it seems she's mistaken the Old Bags Luncheon for a speed dating event. Actress Alana Stewart posted a carousel of photos to Instagram on February 20, 2025, and it's painfully obvious Guilfoyle didn't read the dress code before the event.
The photo Stewart posted with Guilfoyle appears juxtaposed against her photos with the other attendees of the events. Though the two women color-coordinated by rocking blush shades of pink, Guilfoyle's thigh-length dress appears out of place when considering them against the other women's pantsuits. The dress itself was lined with a chain-link overlay and silver trim, and she paired it with a pearl necklace and matching earrings, with a matching acrylic set to correlate with her pink theme.
Guilfoyle is no stranger to having her makeup, fashion, and even plastic surgery called into question, but the smoky eye and excessive skin exposure seem a little over-the-top for a charitable event.
Kimberly Guilfoyle could be trying to get Don Jr.'s attention
Despite Kimberly Guilfoyle and Donald Trump Jr.'s messy split being made public in December 2024, she still maintains close ties with the Trump family, meaning she is well aware of his new budding romance with socialite Bettina Anderson. Could jealousy be what has been motivating her to shed the pounds and wear less clothing, or is she simply trying to move on with her life?
A source told Us Weekly that the two had split back in September 2024 without any bad blood, explaining, "The breakup was amicable and so is their relationship today; they just had different goals." However, she has yet to sell her engagement ring worth hundreds of thousands of dollars, so it seems Guilfoyle is still on her healing journey when it comes to Don Jr. There is certainly an inkling of jealousy in the air, as Don Jr. attended the inauguration hand-in-hand with his new boo, but Guilfoyle was specifically chosen by Donald Trump to be the US Ambassador to Greece. Living out the "Mamma Mia" dream in real life is certainly one way to get over a breakup.