Kimberly Guilfoyle’s Unforgettable Fashion Mishap: A Dress She Can’t Forget

Kimberly Guilfoyle’s sheer catastrophe in 2019 was just one of many fashion fails that would continue to haunt her. While this particular instance was uncomfortable because of her choice in undergarments, Guilfoyle often veers into fashion faux pas or gaudy choices. 

In January 2025, Guilfoyle wore an unforgettably tacky dress. In another instance, people shared pictures of her on X wearing a black dress with sheer front and side panels, in which Guilfoyle looked distinctly uncomfortable. She was covering her abdomen with her arms, and it was difficult to tell if Guilfoyle was embarrassed or just cold. Either way, the dress was the problem. 

We feel for Guilfoyle; she can’t seem to get it right. It’s evident that she has a certain aesthetic she’s going for — Guilfoyle obviously wants to appear attractive and vivacious, what with her body-con dresses, heels, and ultra-glam look. However, her efforts often backfire because they go too far. The fact that she’s a poster child of the Mar-A-Lago face plastic surgery trend says it all. Guilfoyle has taken every form of aesthetic improvement to the ultimate limit, and her fashion fails, like that sheer dress fumble, are simply a part of this larger problem.