Unfiltered Kimberly Guilfoyle Pics Prove Her Makeup Shouldn't Be Photographed Up Close

No matter what you think of Kimberly Guilfoyle, we can likely all agree on one thing: she knows what she likes. And, through it all, no matter how many of her fashion and makeup mistakes we beg her to ditch, she marches on, seemingly unaffected by the beauty advice she surely gets from others. You don't need to be a beauty expert to know that Guilfoyle's makeup is usually a bit on the heavy side, and we seldom see her any other way. Still, as the U.S. ambassador to Greece, sometimes Guilfoyle finds herself photographed from far away or onstage making a speech. And, as such, we understand that she might sometimes have the impulse to sport stage makeup. The problem with wearing stage makeup all day every day? It doesn't look so good up close.

It's often hard to ignore Guilfoyle's makeup fails –  from the severe shape and color of her eyebrows to dark eyeliner all around her eyes and massive fake eyelashes. Yet, Guilfoyle's preferred beauty routine typically seems to look worse the closer you get. And, over the course of her time in the public eye, there have been more than a few pics snapped of her makeup that make this painfully obvious.

Harsh, high-contrast makeup is something that often looks better from far away than it does close up. At the amfAR Gala in 2025, Kimberly Guilfoyle showed us just how severe this can get. An up-close pic of Guilfoyle's full glam showed extremely dark brows and eyeliner with caked-on eyeshadow, cartoonishly big lashes, and creasing concealer. This intense makeup look may have looked a bit less harsh when viewed at a distance, but close-up pics show just how overwhelmed her face is by too-dark products.

Raccoon eyes are a common side effect of the Republican makeup trend, and this unfortunate makeup mistake can be much more obvious from up close. When it comes to her eye makeup, Kimberly Guilfoyle loves all things dark, and this selfie with a friend shows just how over-the-top that can sometimes look. In this photo, Guilfoyle clearly has thick, smudge-y eyeliner all the way around her eyes, as well as dark eyeshadow. This look is overpowering for Guilfoyle, but it probably looked quite a bit less intense from further away. 

Most of us don't have perfectly symmetrical faces, but that's not exactly something we want our makeup to highlight, and we definitely don't typically want it to make us look even less symmetrical. Yet, that seems to be exactly what happened to Kimberly Guilfoyle in a May 2025 selfie with a friend. Guilfoyle sported her usual all-around eyeliner, dark eye makeup, and intense brows. Up close, though, all of it looked a bit lopsided, which was made worse thanks to the harsh colors and application. 

It's no secret that Kimberly Guilfoyle loves her dark eyeshadow. On the first day of the CPAC conference in 2023, though, she outdid herself. Guilfoyle sported dark grey eyeshadow that didn't appear to be blended, at all. The result looked like makeup she may have applied for a "Beetlejuice" Halloween costume and definitely didn't look like a normal full face of makeup. As is often true with Guilfoyle's beauty routine, her sharp, harsh eyebrows made this look even more drastic and costume-y than it already was.

Unfortunately for Kimberly Guilfoyle, her makeup didn't get much better for the second day of the 2023 CPAC Conference. In fact, it may have actually gotten even worse thanks to her enormous eyelashes. With heavy eye makeup like  Guilfoyle prefers, it's no surprise that she typically opts for big false lashes to balance out the look. Up close, though, these lashes are often so oversized that they look distracting and just plain silly.

When your foundation isn't laying right, harsh lighting and a close-up perspective can take your look from bad to worse. Such was the case for Kimberly Guilfoyle at the Republican National Convention in 2024. Guilfoyle probably gave herself a particularly heavy makeup look to be on camera, but when a pic was snapped up-close, it was clear that none of her makeup was laying smoothly, and it all looked totally cake-y. From her uneven-looking foundation and blush all over her face to her chapped-looking lips, this makeup was a total mess. 

In 2019, Kimberly Guilfoyle sported a glam makeup look for New York Fashion Week. From afar, this makeup look may not have appeared quite as harsh as her usual beauty routine does. Up close, though, it was clear that everything was just a bit too pigmented for her. The pink blush, the lipstick, the dark eyeliner — everything just looked too saturated, and the resulting look reminded us of the makeup a clown might wear.