Kimberly Guilfoyle's Latest 'Fit Channels Would-Be Bridal Vibes In Glimpse At What Could've Been

Kimberly Guilfoyle has gamely carried on with life as a singleton ever since her unfortunate uncoupling from Donald Trump Jr. (which sounds better than saying "she was ditched for his mistress"). Granted, it doesn't hurt that Guilfoyle leads a wildly lavish life in Greece as its new U.S. ambassador. Her Instagram account shows her meeting with the country's top political and religious figures by day and attending glam galas at night (often with inappropriately see-through outfits). Every so often, though, a hint of lingering regret makes its way into the feed, as was the case with her latest post.

Guilfoyle shared a December 12, 2025, Instagram photo from GRACE, a Greek women's fashion and lifestyle magazine. The former Fox News host was almost unrecognizably glammed as the cover subject, "photographed ... for the first time at the ambassador's residence," as the GRACE website boasted. Her simple column gown was a far cry from the tight, low-cut minidresses she favors, and her usual tumbling hair extensions were tamed in a chic updo.

Guilfoyle bore a striking resemblance to the legendary Sophia Loren in her 1960s heyday, and many commenters approved. Adjectives like "stunning," "beautiful," and "Greek goddess" were attributed to Guilfoyle in the comments (perhaps for the first time). One follower put it more bluntly: "Finally elegance instead of Frederick's of Hollywood! She looks so much better with her hair up and her skirt at a more ladylike length and her breasts covered."

Other users were fooled by the color and long shoulder cape of her white dress. "Is she getting married?" asked one commenter, with another adding, "Ooooh I thought it was a wedding announcement!" In truth, they weren't wrong, and it's hard not to wonder whether Guilfoyle herself was thinking the same thing.

How time flies. It seems like only yesterday that Kimberly Guilfoyle was showing off her enormous engagement ring from Donald Trump Jr. on his New Year's Eve birthday in 2021. This officialized the relationship status they'd kept secret for months, reportedly wanting to keep the news quiet until they and their children had settled into their new Florida life. However, year after year passed without any sign that the couple was actually altar-bound. Some speculated they were too busy stumping for Don Jr.'s dad, and that they would tie the knot after the 2024 presidential campaign. Yet by the time the election results were in, Don Jr. and Guilfoyle were already finished, and his affair was making the tabloids.

The jilted fiancée quietly stepped aside and was soon shipped off to Greece for a new life and career. Yet for some months, Guilfoyle still wore her engagement ring publicly, giving unhinged ex-girlfriend vibes until she finally let her left hand go bare. She has yet to give any statements about the breakup, which may be out of respect, privacy, or a nondisclosure agreement.

Guilfoyle's Greek magazine cover brought the situation back into sad focus, though; her surprisingly lovely bridal style would certainly have suited a White House wedding. Maybe it would have been the perfect event to launch the opening of President Donald Trump's $300 million ballroom. Now, Guilfoyle is thousands of miles from D.C., while Don Jr. and Bettina Anderson giddily flaunt their romance. With Christmas coming up — a time when girlfriends may expect a new sparkler under the tree — Guilfoyle's holiday may be more blue than white.