Kimberly Guilfoyle's Spicy Outfits After Her Breakup Sent A Clear Message To Don Jr.
No one could ignore the red flags in Kimberly Guilfoyle and Donald Trump Jr.'s relationship for long. Despite their efforts to look like a 2Gether 4Ever duo, the distance between the pair became increasingly obvious as they stumped for President Donald Trump's 2024 campaign. Then Don Jr.'s rumored mistress, Bettina Anderson, quickly upgraded from "rumor" status to official new girlfriend by year's end. Guilfoyle was left with nothing to show for her long engagement but some memories, a nice chunk of ice, and a "don't let the door hit you" ticket to Greece.
The lawyer and former Fox News host continues to support the man who might have been her father-in-law. Her Instagram account could easily be mistaken for the official White House feed, with its constant praise for the president and his policies. Yet while Guilfoyle is staying verbally mum on her ex, her outfits are doing plenty of talking. At every event she attends — charity galas, birthday parties, a Mother's Day lunch with her son — she makes sure to show as much cleavage and leg as possible. The message is clear: "Look what Jr. gave up!" Granted, it does smack a bit of desperation (well, maybe more than a bit), but we have to give her credit for not backing down. Here are just a few examples of her fashion-is-the-best-revenge looks.
Guilfoyle began her thirst-trap campaign before the split was official
Even as Kimberly Guilfoyle might have been secretly fuming over Donald Trump Jr.'s affair with Bettina Anderson, she nevertheless kept up appearances during the election season. If anything, she poured on the spice even more liberally, with gravity-defying minidresses and hair extensions that would make Rapunzel envious. It might not have been the most appropriate attire for CPAC rallies in Bible Belt states, but it solidified her image as the first son's arm candy. Sadly, the ploy backfired. Sources have claimed that Don Jr. disapproved of his fiancée's look and tried unsuccessfully to beg her off the sexy ensembles. Anderson, who radiates an old-money society style, is generally regarded as a better match for the Trump family. Much as that must sting, Guilfoyle refuses to switch out her closet for less provocative outfits.
Guilfoyle may be trying to push back against ageism
Proving the double standard is still alive and well, much was made of the fact that Donald Trump Jr. left Kimberly Guilfoyle, the older of the two by nine years, for a much younger woman. Naturally, the implication was that the former first lady of California was past her prime and no longer worthy of her fiancé's love or passions. Nonetheless, Guilfoyle refuses to change up her style for a more Chico's or Lands' End image. It would seem to be her way of telling the world: "Sexiness is ageless!" For her 56th birthday in March 2025, Guilfoyle gave "Golden Girl" a new meaning with the snug minidress and platforms shown here as she partied down with friends. "Feeling grateful for another year of life, growth, and amazing people by my side," she wrote on Instagram. "Here's to new adventures, laughter, and making the most of every moment!"
Ironically, one of the youngest people in President Trump's cabinet wears more mature outfits than his almost-daughter-in-law. White House Press Secretary Karoline Leavitt's fashion fails are almost a daily occurrence, and one of her most common styling blunders is trying to dress older than her years. Leavitt's reliance on grandmotherly sweater sets, pantsuits, and schoolmarmish outfits may aim to give her more gravitas behind the podium, but it doesn't quite work. The two should consult an expert for a makeover that flatters their ages as well as their figures.
Is Kimberly Guilfoyle going too far?
Pouring on the spiciness seems to be Kimberly Guilfoyle's self-care ritual as she moves on with her post-Trumpian life. The skin-baring red dress Guilfoyle wore to the 2025 AmFAR gala was the ultimate middle finger to Donald Trump Jr. But it's been a hot minute since the breakup, and at some point, she's going to have to realize her style choices aren't doing anything either to bring her fiancé back or to entice any new love interests. Even her fans are begging her to tone down the daring outfits and dramatic makeup. When Guilfoyle posted an Instagram pic of herself in a tight pink minidress at a book event, the comments included: "She looks like a Barbie wannabe," "I would love to see her in more conservative fashion," "I would go a little bit more for the natural look, bit less hair and make up," and the brutal: "{A]m I the only one who thinks she dresses like a whore? There's no reason for her to do so. She can just dress her age."
Guilfoyle has undergone a complete style transformation over the years. As an attorney, she wore courtroom-ready suits; then as the supportive spouse of California Governor Gavin Newsom, she upped her look to suit her status as part of the West Coast social scene. Now that she's embarking on her new life as U.S. ambassador to Greece, Guilfoyle could take the opportunity to reinvent herself yet again. Ditching the provocative dresses and platforms for a more subdued and casual Mediterranean wardrobe, putting in some highlights and embracing a shorter 'do, and going less severe on the eye enhancers could bring out her beauty, improve her rep, and perhaps — finally — elicit a bit of regret from Don Jr.