Kimberly Guilfoyle's Tacky Flapper Dress Steals The Spotlight For All The Wrong Reasons

Kimberly Guilfoyle has taken her one-woman "Frocky Horror Show" on the road again. This time, she gave a notable performance at Donald Trump's pre-inauguration celebration in Washington, D.C., on January 19. Guilfoyle's many fashion fails are pretty legendary at this point, making her a frequent flyer on the worst-dressed lists. And the shimmery beaded fringe floor-length flapper dress she slipped into for the glitzy event is guaranteed to land her a top spot. Guilfoyle's ensemble was made all the more memorable by the giant crystal-studded crucifix she draped around her neck. Moreover, the former Fox News host topped the whole look off with her trademark Elvira-style heavy black eye makeup.

"With our new ambassador to Greece! Beautiful and lovely @kimberlyguilfoyle," Simona Mangiante captioned a photo on Instagram showing Guilfoyle sandwiched between her and her husband, George Demetrios Papadopoulos. Guilfoyle is likely still stinging over her messy breakup from Donald Trump Jr.; however, she managed to put on a brave face, smiling widely for the camera as if she didn't have a care in the world.

Guilfoyle's outrageous and often tacky outfits and questionable style reportedly played a significant role in her former fiancé's decision to end their relationship. "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 dished to People in December 2024. "The tight dresses need to go, and she has been told that." Sadly, the staunch Trump loyalist clearly failed to heed the warning.

Kimberly Guilfoyle has a very distinctive style, and love it or loathe it, you have to give her props for sticking with it come hell or high water. Her tacky fringed flapper dress was ripped straight from the pages of the Guilfoyle Gowns 101 book, and all credit to her; she rocked the fashion felony in her own indomitable way, not caring what the critics thought of it. Her love of skin-tight, revealing dresses and sky-high heels was reportedly the humiliating reason Donald Trump Jr. ditched Guilfoyle for his alleged mistress, Bettina Anderson (in addition to his never-ending quest to please his father Donald Trump, of course). 

"Don Jr. has always wanted to look good in his father's eyes," People's source claimed. "Someone like Bettina, who is and has been a model and is in Waspy circles of Palm Beach, is something that would impress him." The red flags in Don Jr. and Guilfoyle's relationship were glaring and plentiful. So, it was little surprise that, according to Page Six, their split was a long time coming. "Don and Kimberly haven't been getting along over the past year," a source divulged in December 2024. "They get argumentative at Mar-a-Lago in front of people. Nothing crazy, but you know when a couple is fighting. They bicker in public."