8 Times Kimberly Guilfoyle's Outfits Screamed Revenge After Don Jr. Split

Following her 2024 split from Donald Trump Jr., Kimberly Guilfoyle hasn't been shy about letting the people know she's still here. The former Fox news star has been seen out and about wearing several outfits that signal she's out for revenge — or at least ready to make her ex feel some regret. Having dated Trump from 2018 to 2024, it's understandable why. During her time with him, she became a  prominent figure within the MAGA community, having expressed her support for Trump's father, President Donald Trump on multiple occasions. 

Still, not everything is meant to last forever, but in this case, it's fair to assume Guilfoyle may have some lingering feelings. Shortly after their split, it was revealed that Don Jr. had seemingly moved on to socialite Bettina Anderson. Guilfoyle, meanwhile, was named ambassador to Greece by President Trump, and remains deeply involved in the family politics. As such, both she and Don Jr. end up spending time in similar circles. And judging from her outrageous, sensational outfits, it looks like Guilfoyle is serving one revenge dress after another, giving Don Jr. a taste of what he's missing. 

The only problem is that Guilfoyle repeatedly lands on the worst dressed lists. There's one gaudy dress style in particular that Guilfoyle can't seem to let go of, and around the time of Trump's second inauguration in January 2025 — which also happened to be right around her split from Don Jr. – Guilfoyle's inauguration looks were some of her most questionable ones yet. Even Guilfoyle's Grand Prix outfit, which she wore in May 2025, looked like a cheap inspiration from Forever 21. She's clearly dressing for revenge, but whether or not she's getting it is another story. 

While news outlets were buzzing about Donald Trump Jr. and Bettina Anderson becoming a hot, new item, Kimberly Guilfoyle was opting for the color of passion as sweet revenge. She attended the 31st amFAR Gala in Cannes in May 2025 wearing a very sheer, red gown. Half of the gown was covered in satin, while the other half was mesh, save for some strategically placed embroidered flowers and vines.

To commemorate her birthday in March 2025, Kimberly Guilfoyle posted a photo shoot to Instagram of herself posing in a mini, bodycon gold dress with platform sandals and a big, huge blowout. The one-sleeve getup and caption seemed to be a glitzy way of signaling she wasn't ruminating on her and Donald Trump Jr's former relationship. "Here's to new adventures, laughter, and making the most of every moment!" she wrote. Guilfoyle wanted to make it very clear that she wasn't looking back! 

We love a petty queen. Kimberly Guilfoyle seemed to be out for revenge by posting photos of herself to Instagram with two unnamed hunks on March 28, 2025. Don Jr. who? She wore a black gown with a plunging neckline and sheer panelling along the corset-style top. To deflect from the real intention of the post, Guilfoyle commented on the Wags to Riches Gala that she was attending, noting (not so subtly) that she was honored with "Cigo" award for kindness to animals. 

Another day, another dude. Kimberly Guilfoyle posted a photo with author and dermatologist Nicholas Perricone. She held up his book "The Beauty Molecule" and wore a mini, Barbie-pink dress. The fitted number featured long sleeves and highlight her assets, leaving room for her huge hair to steal the show. Unfortunately, the revenge look backfired, as people gave criticism on Instagram. "I would go a little bit more for the natural look, bit less hair and make up," someone wrote. "Beautiful lady, too much hair," another added. "I love, love Kimberley but.... I would love too to see her in more conservative fashion style," a third noted. So it wasn't such a hit. 

To celebrate Cinco de Mayo, Kimberly Guilfoyle posed with friends at a party in May 2025. For the occasion, she wore a red and black lace dress that featured a corset-like top with black heels and a black blazer hung over her shoulders. The lingerie-inspired dress fitted her figure perfectly, flagging to Don Trump Jr. that he was old news. As usual, Guilfoyle sported her signature hairstyle: a larger-than-life blowout worn long in loose curls. It was quintessential Guilfoyle. 

While we'd love to think that anyone can wear anything at any age, Kimberly Guilfoyle's white, summer outfit might be an exception. She posed with her son at the Monaco Grand Prix in June 2025 wearing something that seemed a little too youthful. She wore a white skirt with a floral bra top and an open blazer, along with white, platform sandals. People seemed to recognize immediately that Guilfoyle was flaunting a revenge outfit, as Donald Trump Jr. came up in the comments repeatedly. "Love you Kimberly sorry things didn't work out with Don Jr. but things will get better," one person sympathetically commented, making things even more awkward. "You are gorgeous and smart compared to the cookie cutter blonde Jr. is with now," another wrote, referring to Bettina Anderson. Ugh, it's just so embarrassing. 

Kimberly Guilfoyle posed next to her son, Ronan Anthony Villency, while traveling in Europe in June 2025. The former Fox News anchor, and former fiance of Donald Trump Jr. gave major drama in a satin, pink gown with a tonal, pink fluffy jacket. Guilfoyle looked like a star, and people were sure to let her know. "Beautiful! Don Jr.... You messed up!" someone wrote, giving her ex a shout-out. Someone else pointed out that Guilfoyle was single, saying: "[T]he great thing of having boys is that they are our plus one too." Ronan's presence was clearly much appreciated.

To celebrate Mother's Day in 2025, Kimberly Guilfoyle posted a series of photos with her son, Ronan Anthony Villency, and the pics were a not-so-subtle attempt at showing Donald Trump Jr. what he was missing. She wore a micro pink babydoll dress with a white collar, and people couldn't handle it. "Why are you dressed like an American girl doll???" someone asked, roasting the outfit. "Trying to look young. Lmao," another commented. "Betty Boop... you okay?" a third asked. The babydoll dress might not have been such a great idea.