Kimberly Guilfoyle's Spicy Mini Dress Moment Is An Inappropriate Outfit Fail We Can't Forget

Kimberly Guilfoyle's split from Donald Trump Jr. might be her smartest move yet. The former Fox News host is free to enjoy her new post as U.S. Ambassador to Greece. High-profile magazines are reportedly wooing her as a cover profile, which should ease some of the sting of Don Jr.'s girlfriend's humblebrag that Forbes considers her a new style icon. But if Guilfoyle really wants to shine in her next life stage, she could start by revamping her wardrobe. Guilfoyle's history of inappropriate outfits is well known by now.

In March 2024, Guilfoyle attended a fundraiser for Tommy Tuberville, the football coach-turned-senator who plans to run for Alabama governor in 2026. She posted a carousel of pics from the day on her Instagram account. While other women at the event wore longer dresses and blouse-shirt combos, Guilfoyle arrived in an outfit similar to ones she's worn in the past. The hem of her red mini coatdress stopped just short of her upper thighs, and the neckline dipped down far enough to show a decent amount of cleavage. As if the dress weren't eye-catching enough, it also featured three oversized rhinestone buttons shaped like flowers. It would have been perfect for a date night with Don Jr., but not for a sedate afternoon with conservative political supporters. Even her photos sent a mixed message: Along with shots of her with Tuberville and other guests, Guilfoyle put up a solo shot in which she assumed her typical hand-on-hip modeling pose.

Did Kimberly Guilfoyle steal too much Trump thunder?

After nearly five years as an engaged couple, Donald Trump Jr. and Kimberly Guilfoyle called it quits in 2024. The more obvious reason behind the split was Don Jr.'s new girlfriend, Bettina Anderson, but there was apparently more to the breakup, according to a source who spoke to People. Reportedly, the first son was embarrassed by his fiancée's insistence on wearing overtly sexy outfits everywhere from her home kitchen to awards events and photo ops with President Trump. "The tight dresses need to go and she has been told that," said the insider, adding that Anderson's style was a better fit for the family: "Don Jr. has always wanted to look good in his father's eyes." 

But why would a man who owned the Miss Universe Organization — and whose wife is a former model — be concerned about having a daughter-in-law who wears sexy outfits? Could it be that Don Jr. was afraid Guilfoyle would be too much of an attention grab?  Remember, the president goes around with baseball caps saying he was "right about everything" and uses his social media to demand the Nobel Peace Prize. Donald Trump has such a massive ego, he's even been seen wearing a tacky lapel pin with his own likeness. If the marriage had gone through, the newest Mrs. Trump might have been forced to rein in her style to make sure her father-in-law would stay front and center in the public eye. 

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