Jeanine Pirro's Biggest Makeup Fails Hint She's Taking Tips From Kimberly Guilfoyle

As someone on television, one of the worst mistakes you can make is getting washed out by lighting. The harsh studio lights above the anchor desk are one of the main reasons newscasters have to pack on as much makeup as they can. But for one prominent anchor, knowing the difference between an elegantly defined face and clown makeup is like treading a tightrope. 

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Co-host of Fox News' "The Five" Jeanine Pirro knows how to put on her face before every live segment, so much so that she is one of the many news anchors who look unrecognizable without their makeup. But even makeup masters like Pirro aren't exempt from a few bad cosmetic days. In one of the biggest news anchor makeup fails of 2024, Pirro shocked the photographers at the 2024 Fox Nation Patriot Awards with her gaudy, black eyeliner. She took the pencil so hard to her face that her eyes looked cartoonish, instead of the doe-eyed look for which she was probably hoping. 

The heaviness of the eyeliner gives us all deja vu to one of the makeup mistakes we're begging Kimberly Guilfoyle to ditch in 2025. In the Instagram launch of her book "The Princess & Her Pup" in May 2024, Guilfoyle sported a wildly bold makeup look, which included a pair of heavily lined raccoon eyes — not to mention her Facetune fail. This cosmetic faux pas is just one instance that makes us believe Pirro is taking makeup tips from caked-face Guilfoyle. 

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They're both buried in false lashes

Jeanine Pirro isn't the expert behind her appearance. The former judge introduced her glam squad on Instagram in February 2025, which included a hairstylist, a makeup artist, and an assistant. "Team work makes the dream work!" Pirro wrote in the caption. It certainly does because it must take a team to glue those false lashes on her eyes daily. Her strip lashes are so long that her eyes disappear behind them when she smiles.

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Pirro might be taking a page out of the MAGA makeup playbook because she's starting to seriously morph into Kimberly Guilfoyle, whose falsies are big enough to sweep up Pirro's Fox dressing room. In a Facebook selfie from 2021 — a great example of the false lashes in question, fans of Guilfoyle tried to give her advice in the comments. "Such a great lady! But I agree with the others to tone down the make up. I've seen older pictures and your natural beauty is just stunning. Let it shine lady!!" one user opined. Maybe that's the uniform for "The Five," since both women have worked on the show, but given Guilfoyle is no longer an employee, we're hoping she gives up the heavy makeup look soon.

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