Outdated Outfits Kimberly Guilfoyle Never Should Have Worn

Let's face it: Kimberly Guilfoyle isn't known for having the best sense of style. From Kimberly Guilfoyle's inappropriate Hamptons outfit that didn't do her any favors to her super-embellished dresses at political events, the former Fox News host loves to put on a spectacle via her clothing, even if it makes her look sadly outdated. It doesn't help that Donald Trump Jr.'s ex also loves piling on makeup, which dates her even more. Somebody needs to tell her that the natural look is in right now.

Although Kimberly Guilfoyle has had a complete transformation since her days as the first lady of San Francisco, she's stuck in the past when it comes to her wardrobe. Her motto seems to be that more is more, and while we love a good show-stopper, the ambassador to Greece turns heads for all the wrong reasons with some of her looks because of old trends like tight sweater dresses and large '80s shoulders.

Not only did Kimberly Guilfoyle's risqué gala outfit push boundaries (even for her), but it was also horribly outdated. The big, puffy sleeves and excessive lace detailing made the former prosecutor look like she stepped off the set of "Dynasty," and we're not talking about the reboot. The '80s look didn't do Guilfoyle any favors, especially with her smokey eyes and silver platform sandals. Don't even get us started on how inappropriate the peekaboo style was for the annual AmfAR Gala Cannes, which was held in May 2025. We just hope there were no wardrobe malfunctions that night.

Kimberly Guilfoyle sure loves revisiting past trends, including the body-hugging sweater dress she wore to a Daily Mail holiday party in 2019. She looked straight out of the Y2K era, especially with the sparkly fuzzy material enveloping the frock and opaque black tights that were popular during the time. That's not to say that sweater dresses aren't in style in any capacity, but these days, the slouchy look is more on-trend. And you should say "no" to wearing them with tights, of course. Instead, try sheer stockings and chic knee-high boots. 

Kimberly Guilfoyle made another 2000s fashion misstep when she wore low-waisted capris to a Hamptons event in 2018. It looked like she had dug into her Y2K wardrobe and dusted off those pants because no one was wearing low waists at the time. Guilfoyle's outdated 'fit was only highlighted even more by her cropped shirt, which showed off her navel. While the top and bottom were fine separately, together, the whole ensemble was a hot mess and dated.

We often see Kimberly Guilfoyle in out-there outfits studded with sparkles or embroidered lace, often with a low-cut top. That's why it was shocking to see her in a plain white dress with a crew neck and long sleeves at the "Évocateur: The Morton Downey Jr. Movie" premiere in 2013. With the wide black belt and the hemline falling just at her knees, Guilfoyle looked like she pulled out her junior-high dress for picture day. This was before she started dating Donald Trump Jr., so perhaps she hadn't yet been introduced to the art of MAGA dressing just yet.

One would think that wearing a see-through dress to an event filled with world ambassadors would be inappropriate, but Kimberly Guilfoyle obviously did not. The political commentator showed up to The Hellenic Initiative's 9th Annual Gala in October 2025 in a bright-red gown featuring sheer arms and a skirt resembling mesh. While the other attendees were dressed in their best formal wear, Guilfoyle looked like she was ready to boogie down at a beach party. We get that she's only been an ambassador for a short time, but she should take some style cues on what not to wear to a gala with government officials.

Barbiecore fashion took over the world in 2023 when the hit film "Barbie" came out, and all you could see was pink everywhere. We totally leaned into the trend, but when the moment passed, we stashed away our bubblegum-colored 'fits. Unfortunately, it looked like Kimberly Guilfoyle was still living in Barbie's Dreamhouse when she posed with her son in a bright-pink tweed dress for Mother's Day 2025. This look would have been perfect for the movie premiere or a watch party a couple of years ago, but now, it just looks passé.