Kimberly Guilfoyle's Most Inappropriate Dress Is A Fashion Disaster She'll Never Live Down

Kimberly Guilfoyle shocked spectators when she stepped out for Zang Toi's fashion show in New York City in February 2019. Guilfoyle wore a sheer black dress with pink butterflies on her left shoulder during New York's Fashion Week, but didn't go with the right undergarments. She appeared to wear nude nipple pasties and nude underwear, but the dress was still surprisingly, even uncomfortably, sheer.

Now, don't get us wrong. We love a good translucent top. There are plenty of ways to ace the sheer clothing trend and still look fabulous. Unfortunately, Guilfoyle's look was not fabulous for so many reasons. For one, she wore the dress in New York in February. For anyone familiar with the region, it is cold as ice that time of year. So her dress, which would be somewhat more acceptable in a tropical locale, was uncomfortably uncovered for such a chilly time of the year. It was completely seasonally inappropriate. 

Secondly, she attended the event with her then-fiance, Don Trump Jr., clearly affiliating herself with the Trump family. There's a certain level of decorum that one expects from a political family and it's politically adjacent members. Even though this was a fashion event, Guilfoyle was still presumably representing a political realm, which made her transparent choice that much more surprising.

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.