5 Times Kimberly Guilfoyle Went Overboard With Tasteless Makeup & Looked Totally Out Of Place

One thing about Kimberly Guilfoyle is that no matter the time or place, the former Fox News personality will most likely be rocking a full-glam look. She loves being dolled up so much that a source once told The Daily Beast that when she worked for Fox News, Guilfoyle would often use the cable giant's makeup team for personal events, which she wasn't supposed to be doing — but it just goes to show that Guilfoyle loves a full face everywhere she goes. 

While there are times that Guilfoyle has gone without any makeup, it is rare, as she has established a signature look. Her day-to-day makeup is often featured on her social media. In one Instagram post from May 2024, Guilfoyle rocked her usual makeup look for a Truth Social event. The former television personality's typical glam features a dark eyeshadow with lashes, foundation, and some sort of nude or neutral lipstick. Picture after picture, event after event, Guilfoyle will wear this type of makeup, and sometimes, it's not the most appropriate, considering the event. We're used to seeing the public figure sport inappropriate outfits without shame, but she does the same when it comes to her glam, and we are taking a look at some of the moments where she may have gone a bit overboard with her makeup.

We don't know if Kimberly Guilfoyle took inspiration from her book, "The Princess & Her Pup," in an attempt to look like a princess, but her ensemble for her the tome's launch just seemed a bit much. In May 2024, the former television personality posted a photo to Instagram in honor of the work, wearing a white ballgown-styled dress with heavy makeup — and we mean heavy makeup — that distracted from the event. Her eyeshadow was packed on and was so dark that it made her eyes nearly unrecognizable. Still, Guilfoyle smiled wide as she took a photo with the book, writing in her caption, "More and more American families are eager to support the companies that support them. It's why I partnered with Brave Books on 'The Princess & Her Pup,' a wholesome and heartfelt story about the importance of friendship and the value of courage. Together, we can all bring more positivity, joy, and grace into this world." 

Guilfoyle has been on a promotion tour for "The Princess & Her Pup" and has made sure to be glammed any time the book is involved, even if it's in the background. In May 2024, she posted a clip of "The Kimberly Show," where the project stood on a shelf behind her. Of course, she was sporting makeup in the video, but her glam throughout the promotion just seems over the top for a children's book. 

If there is one place you're not expecting someone to turn up in full glam, it's the carnival — aside from maybe the clowns. However, Kimberly Guilfoyle proved that even at family outings, she is going to go out there and rep all the cosmetic products she owns. Guilfoyle and her fiance, Donald Trump Jr., took the kids out for a night of fun and shared pics of their outing to social media. She wrote on Instagram, "Don Jr. and I had an incredible time at the @admiralscovelife carnival last night with our kids! @admiralscovelife, you really outdid yourselves this time. We cannot wait until next year! @donaldjtrumpjr." The photo seemed sweet, but the former Fox News correspondent looked totally out of place and mismatched with Don Jr. and the rest of the family. While the Trump family was makeup-free and in chill outfits, Guilfoyle was the opposite. 

Guilfoyle packed on the foundation, blush, and eyeshadow and tried to outshine the rest of the Trump family, but it just made her look like the odd one out. Not just that, but she also wore a short, long-sleeve mini dress with heels that were unsuitable for a carnival. Even her followers pointed out the difference. One user wrote, "Love it the kids are in normal clothes!" In the end, Guilfoyle's whole look just seemed a bit tasteless for such a chill event. 

We have a bone to pick with one of Kimberly Guilfoyle's bold makeup looks because it just seemed totally unnecessary. The public figure shared a photo introducing a new Trump family member to her followers back in June 2023. She shared, "Introducing Chela Guilfoyle Trump AKA Princess Peach! Thank you Jason Gluck and @furryfriendsjupiter for rescuing the mother and father so that this baby girl could be born! Mario and Luigi love their new baby sister!" In her carousel of photos, every image featuring Guilfoyle and Chela showed the former television personality in her usual dark makeup look. 

Guilfoyle's overuse of cosmetics already seemed strange since they were simply introducing Chela, but what made it even more bizarre was that Don Jr. looked as laid back as could be. The businessman was in one of the photos with the new dog, and he wasn't dressed up, nor did he have any makeup on. Even in a photo from what looks to be a chill day at home, Guilfoyle still had a full beat as she held the new pup close to her chest. 

Months later, she shared a post alongside Chela at a fundraising event for rescue animals. Guilfoyle had once again overdone her makeup, but at least this time, it made a bit more sense, considering it was for a fundraiser and not just introducing a dog to the world of social media.

Kimberly Guilfoyle went all out with her cosmetics for a luncheon fundraiser, but her look just didn't land. In February 2024, she shared photos at an Old Bags Luncheon alongside some of her friends. According to the Old Bags Luncheon website, the purpose of this event is to gather unused handbags donated by individuals with the intention of raising money. While it's not unusual for people to wear makeup at these fundraising events, Guilfoyle's look was totally outdated compared to her peers. 

Guilfoyle's heavily edited makeup made her look like she was stuck in 2016, and hadn't updated her routine since. We know she loves to wear darker eyeshadow, but it doesn't go with the clean girl aesthetic that her friends were going for in the photos she posted to Instagram. She looked like the odd one out with her glam that looked more for a night out than a lunch gathering. Still, despite being the most made-up one there, it didn't get her down. She shared in her caption, "What a fantastic day supporting a great cause at the annual Old Bags Luncheon! Grateful for the opportunity to raise awareness and funds for the Center for Family Services at such a lovely venue. Huge thanks to @oldbagsluncheon for organizing such a wonderful event and for their ongoing commitment to @cfspbc!"

Yes, for Kimberly Guilfoyle she even needs makeup when she is taking part in outdoor activities. While most people would go barefaced for such things, the former correspondent wouldn't be caught without her usual glam. Sharing a selfie after a weekend of recreational activities on Facebook, Guilfoyle wrote, "Great weekend enjoying the outdoors with @donaldjtrumpjr @fieldethosjournal @kuiu_official #outdoors #longrange." The closeup photo gave people a good look at what cosmetic products she used for the day. From the photo, it looked like Guilfoyle had her eyebrows filled in, a heap load of eyeshadow, false lashes, foundation, and so much more.

The public figure's makeup look seemed a bit unfit for all the outdoor activities she took part in, and even her followers took notice. One person shared, "Who camps with all that makeup? That's not you!" The online user was wrong about one thing — it is Guilfoyle! She loves to wear makeup when it doesn't seem appropriate, and this wouldn't be the last time she wears a full face of makeup for outdoor activities.

In August 2023, Guilfoyle shared a carousel of photos of her, Don Jr, and their kids, enjoying a fishing trip. In a selfie with Guilfoyle's son, Ronan, followers could see the former Fox News personality was wearing some sort of makeup, despite trying to hide it behind some big shades. Clearly, she doesn't care what people think about her decision to wear makeup in unfitting situations.