Kimberly Guilfoyle's Revenge Outfits Post Her Breakup With Don Jr.

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Kimberly Guilfoyle attending the first day of the Republican National Convention at the Fiserv Forum

Andrew Harnik/Getty Images

It’s no secret that Kimberly Guilfoyle’s had a rough go of it. Amid the very public demise of her relationship with Donald Trump Jr., followed by his ultra-quick (and perhaps even overlapping) romance with Bettina Anderson, ultimately solidifying her rise and fall in Trump Land, no one would blame her for feeling like a scorned woman. But now it appears she’s not getting mad — she’s getting even.

Draw the cat eye, sharp enough to kill a man?! As you may recall, it was rumored that her inappropriate outfits were actually partly to blame for the breakup with Don Jr., and even reportedly landed her on Donald Trump’s bad list. “Don Jr. has been telling people for months that Kim is so uptight and always dresses so professionally in these kinds of dresses and high heels, and never looks relaxed or casual,” a source told People in December 2024. “The tight dresses need to go and she has been told that.” Perhaps that explains her noticeable style change before the bombshell split? Alas, now it seems that Guilfoyle is doubling down and digging her infamous sky-high heels all the way in, most likely in hopes of exacting spiteful revenge on her ex-fiancé.

Did Kimberly Guilfoyle try to beckon Don Jr. back with a poofy purple dress?

As the old saying goes, hindsight is always 20/20. Before Kimberly Guilfoyle and Donald Trump Jr.’s split was official, she seemed to be trying to win him back — sporting dresses that left little to the imagination, as if to remind him what he was walking away from. Case in point: a violet-hued dress that left her bare back on full display. But that’s not all. The dress was adorned with a large-and-in-charge bow, fluffy feathered off-the-shoulder sleeves, and a big ol’ brooch pulling it all together. (Is it your birthday, girl?! ‘Cause you look like a present.)

Guilfoyle posted a pic of herself donning the backless garb to her Instagram Stories on September 17, merely two days after Daily Mail published photos of Don Jr. and Bettina Anderson sharing a meal together in Palm Beach. “They were definitely on a date,” a source told the British tabloid. Unfortunately for Guilfoyle, it doesn’t appear that her come hither frock helped woo Don Jr. back. Womp, womp, womppp.

Business casual takes on a whole new meaning for Kimberly Guilfoyle

Even amid rampant breakup rumors, in the political world, the show must go on! Deep in the throes of a rumored split, it was still business as usual for Kimberly Guilfoyle and Donald Trump Jr. when they embarked on a campaign trip to the Balkans. As one can imagine, however, Guilfoyle worked overtime, seizing the moment to show Don Jr. what he was really missing. On September 25, she posted photos from the trip, wherein she donned (see what we did there?) several skimpy dresses, including a strappy little black number with a seriously plunging neckline, to boot. “Incredible trip to Belgrade, Serbia and Bucharest, Romania with @donaldjtrumpjr,” she penned in part.

Ambassador to Greece but make it cute

Shortly after being shipped off — erm, tapped — as the new ambassador to Greece by her ex-fiancé’s famous father, then-president-elect Donald Trump, Kimberly Guilfoyle once again took an opportunity to flaunt her body in yet another revenge dress. On December 17, 2024, Trump Victory Fellow Sammy Balyasny posted a photo of himself posing with Guilfoyle on Instagram. “America, meet your next Ambassador to #Greece Kimberly Guilfoyle,” he gushed in the caption. As evidenced in the photo, while Guilfoyle was preparing for her ambassador era, she still had time to moonlight as a revenge enthusiast via a navy body-hugging mini dress with a deep neckline. Eat your heart out, Don Jr.!