Kimberly Guilfoyle has worn more than her fair share of inappropriate outfits over the years. At one point, rumors even claimed Donald Trump Jr. broke up with her because of them. While that breakup gossip was never confirmed, if it were true, her critics won’t be thrilled to see that her post-Don Jr. wardrobe makes her old looks seem modest. One recent look was so risqué, Guilfoyle didn’t post it to her social media. And we know it wasn’t just an oversight because she shared a heavily cropped, toned-down version of the photo instead.
In May 2025, the former Fox News host visited France for the amfAR Gala, showing up in a fiery red dress that left very little to the imagination. The bodice was almost sheer, stopping just shy of a full nipple reveal. It was designed with only a few embroidered vines pretending to offer coverage, as well as some embellishments. The skirt was floor-length and would have been decent if half of it weren’t made from the same see-through fabric. Guilfoyle paired the look with shiny silver pumps that matched the sparkle of the dress, making the entire look even louder.
Between the risqué cut, the excessive fabric, and the complex paneling, we instantly spotted the work of her go-to designer, Oscar Lopez. She’d actually worn the same dress for Metropolitan Palm Beach magazine. However, when Guilfoyle posted the magazine shots to Instagram, where she credited Lopez, she omitted the sheer skirt and gave a side view with her draped hair covering the full extent of its risquéness. Interestingly, Lopez is behind some of the Trump family’s most controversial fashion moments. He’s the mastermind responsible for Guilfoyle’s cheap-looking yellow dress (which had X in stitches), as well as Lara Trump’s wildly inappropriate 2023 New Year’s outfit. And yet, Guilfoyle remains a loyal fan. Clearly, there’s a market for Lopez’s brand of theatrical, bare-all fashion.
Despite the ever-growing criticism of her fashion sense, Kimberly Guilfoyle’s post-breakup wardrobe shows no signs of change. While her Instagram is now mostly filled with political content, the personal photos she shares double down on her signature style. In March 2025, she celebrated her birthday with a series of Instagram photos in a short, tight gold dress featuring mismatched sleeves, which is a design detail she’s clearly growing fond of. It was skimpy, sparkly, and unmistakably Guilfoyle. Just a month later, she stepped out in another short number at the Impact Wealth Media cover party. This time, the dress was bright pink and barely grazed her mid-thigh: a length that would get most female politicians side-eyes and op-eds.
Still, Guilfoyle seems hell-bent on making one thing clear: She’s not taking fashion advice from anyone who isn’t fully on board with her aesthetic. And while there’s something to be said for her unapologetic commitment to her style, we can’t help but wonder how she’ll navigate the rules that come with her appointment as ambassador to Greece. There’s always room to put your own creative spin on corporate wear, but most official job descriptions involve some guidelines, and ambassadorship is no different.
The official rulebook for U.S. diplomats requires women to wear conservative attire, particularly when abroad in countries with different dress standards than the U.S. That means no short skirts, no low necklines, and no exposed arms. If those three features are off-limits, most of Guilfoyle’s wardrobe doesn’t stand a chance. When she appeared before the Senate in July, she was clearly offering a preview of what she thinks passes for appropriate, with the pantsuit she wore. But old habits die hard, and we wouldn’t be surprised if Guilfoyle ends up making headlines in Greece’s tabloids for all the wrong reasons.
