Kimberly Guilfoyle's Inappropriate NYFW Dress Will Always Haunt Her
Kimberly Guilfoyle has suffered quite a few fashion mishaps that have left heads turning over the years, which is bound to happen when she clearly dresses to get noticed. Known for wearing boldly colored dresses with plunging necklines, Guilfoyle rarely makes it onto best-dressed lists. One particular fashion fail will never be erased from her sartorial history, and that's the black, see-through Zang Toi dress Guilfoyle wore to the designer's show during New York Fashion Week in February 2019.
What the former prosecutor should have been wearing under her on-trend sheer clothing were appropriate undergarments, but all Guilfoyle had on were a couple of pasties and what looked like nude underwear. Sadly, Donald Trump Jr. must not have given her a once-over before they left the house, or if he did, it was too dark to see how sheer the dress would be under bright lights. If Guilfoyle knew that her dress was so transparent, she didn't let on. Rather, she was captured smiling as she sat in the front row with her then-fiance. Unfortunately, it seems she didn't learn her lesson, as she had another inappropriate moment that was even more scandalous than her fashion-week faux pas a few years later.
Another Kimberly Guilfoyle fashion mistake was worse than the first one
We get that the sheer look is in, but Kimberly Guilfoyle took tacky to the next level with a gauzy dress during a 2024 fundraising event at Mar-a-Lago. The black sheath dress featured gold and silver sequins sewn on the bodice, but they did nothing to cover up the fact that Guilfoyle was clearly not wearing a bra or even a pasty. Perhaps this look would have been appropriate at a nightclub, but for a political gala, the commentator looked ridiculously out of place. It's a good thing Guilfoyle had an in with the Trumps, or she probably would have been turned away at the door. Luckily for her, the dress didn't look as sheer from further away, as seen in the picture above. But up close, it was extremely noticeable.
Kimberly Guilfoyle's outdated eyeliner wasn't the only thing folks noticed about her that night, and for good reason. One X user posted a picture of her cringey outfit and wrote, "Kimberly's not leaving much to the imagination at these Mar-a-Lago fundraisers." Another user commented, "Desperate much?" A third even noticed Tiffany Trump smirking in the background and quipped, "Tiffany isn't impressed." If Guilfoyle wanted attention that night, she sure got it, and tragically, the inappropriate 'fit will live on forever thanks to the internet.