Kimberly Guilfoyle's Awkward Mini-Dress Clashes With Don Jr.'s London Date Night Attire

You can always count on Kimberly Guilfoyle to cause a stir with her risky fashion choices. From Guilfoyle's vampy look that had her sticking out like a sore thumb at a local fundraiser to her failed attempt at the coquette trend for the former district attorney's son's prom, Guilfoyle has a penchant for wearing the most inappropriate outfits to the extent that even certain Trump supporters have turned against her. In the latest in her string of fashion disasters, the former Fox News host stepped out for a date night with her fiancé, Donald Trump Jr., on June 12, 2024 in London, clad in an awkward mini-dress that screamed the opposite of class and glamour. She was photographed leaving the restaurant in her geometric-print dress, which Guilfoyle paired with matching earrings, white pumps, and her signature smoky eye look. The flashy outfit clashed with Trump Jr.'s more formal attire, consisting of a blue suit, light blue necktie, and a white button-down shirt.

The fashion faux pas comes a little over a week after Guilfoyle was smoked online for butchering Barbiecore in her favorite tragic silhouette, thanks to her ensemble at a fundraiser. Guilfoyle, who served as one of the guest speakers, took to the stage in a pink, Rebecca Vallance dress with puffed sleeves and a cut-out that showed quite a bit of her chest. "Kimberly get a new fashion designer," one fan quipped in response to photos posted on her Instagram. Others didn't appreciate how they could see her cleavage, with another commenter complaining, "I love President Trump but not your boobs hanging out."

Much like the Biebers, soon-to-be-wed Kimberly Guilfoyle and Donald Trump. Jr are making a case for mismatched couple outfits, haters and fashion critics be damned. The two have showcased their opposing styles on several occasions such as in May 2024, when Guilfoyle took to Instagram to honor their anniversary. "What a blessing to celebrate another anniversary with my soul mate and forever best friend," she captioned an image of herself in yet another pink Rebecca Valance piece. Trump Jr., meanwhile, cut a significantly more casual figure in a plaid shirt underneath a blue blazer with gray pants. Likewise, a month prior, Guilfoyle wore a sexy tube dress alongside her fiancé, who looked sharp in his blue suit, matching shirt, and black leather belt. "Ugly," a netizen wrote of Guilfoyle's look on X, formerly known as Twitter. Others described it as reminiscent of a backsplash wall and a bathroom tile. "Studio 54 wants [their] patrons back," another critic joked. 

In May, a fashion expert who exclusively spoke to The List about Guilfoyle suggested that she should trade her trend obsession for a more timeless style. Instead of sparkly dresses and ill-fitted clothes, the former Fox News host should opt for more structured and sophisticated attire, including clothing that hugs her body instead of showcasing too much skin. According to fashion stylist Michelle Washington, "She should continue to wear what makes her feel confident and comfortable, while also being open to exploring new styles and trends that resonate with her personal aesthetic."