What Kimberly Guilfoyle Looks Like Without Makeup

If there's one thing we know for sure about Kimberly Guilfoyle, it's that she loves her glam. Heck, she loves it so much we may as well call her Kimberly Glamfoyle. That's because she's proven she's certainly not afraid to wear eye-catching makeup and clothing — even at the most inappropriate moments. The political figure, who is engaged to Donald Trump Jr., is rarely seen without a full face of makeup, including her signature heavily lined eyes and glossy nude lips. And there's absolutely nothing wrong with that if it's what makes her feel confident. 

In fact, Guilfoyle is such a fan of being made up that a source claimed to the Daily Beast in 2019 that she supposedly asked the hair and makeup team at her former Fox News gig to do her glam for events outside of the network. But, seeing as we're so used to seeing her all dolled up, we can't help but wonder what she really looks like when she wakes up in the morning before hitting the makeup chair.

Luckily though, we don't have to wonder. Though the former advisor to Donald Trump clearly isn't a fan of being spotted sans makeup, we have seen her a few times without her signature smokey eye and full-coverage foundation — and we have the photos to prove it. It turns out Guilfoyle is just as stunning without the cosmetics because her makeup-free snaps show she's a natural beauty born with clear skin and a cheek contour to die for.

Back in 2017, we got a surprising rare sighting of Kimberly Guilfoyle without makeup. Even more surprising? She actually shared the photo online herself. The makeup-free snap was posted to Guilfoyle's Facebook page and showed her sitting with her son Ronan Villency at the airport. The candid upload featured the two waiting for a flight to Virginia. Guilfoyle captioned it: "En route to emcee the 5th Annual Purple & Gold Gala @ the Army Navy Country Club in VA! God bless our Veterans." Even totally casual and without rocking her usual vampy style though, Guilfoyle still looked stunning. She wore her long brunette hair down and sported a more understated outfit, choosing to dress all in black for her travel day seemingly without so much as a little lipgloss.

Hopping on a jet bare-faced doesn't seem to have become a habit for Guilfoyle, though. Well, at least not after she began dating her now fiancé Donald Trump Jr. in 2018. That's because as a Trump family member, she started taking a much more prestigious approach to travel. In 2021, she was seen disembarking from Air Force One in Florida while arm in arm with her partner — and a full face of makeup.

When Mother's Day 2024 rolled around, Kimberly Guilfoyle shocked her Instagram followers with a photo showing her looking more natural than most fans had ever seen her before. The image was a throwback taken shortly after Ronan's birth in 2006. In the pic, which showed Guilfoyle from the side and seemingly sans hair extensions, Donald Trump's future daughter-in-law wasn't wearing a stitch of makeup as she cuddled her new baby. Her skin glowed without any foundation and the snap also proved she has large, luscious lips even without lipstick, liner, or gloss. 

The snap also made it clear Guilfoyle didn't need concealer under her eyes, as her skin was sans dark circles and eye bags — although that may have changed as she embarked on her motherhood journey! The au natural photo was a world away from her usual heavily made-up (and seemingly airbrushed) Instagram uploads, though it was still sandwiched in between newer photos of her looking more recognizable.

But Guilfoyle's no-makeup throwback didn't mark a permanent change for her Instagram. On May 16, a few days after she shared the batch image upload, she was back to posting super glam pictures and uploaded a photo wearing her signature heavy eyeliner and dark shadow to promote her book, "The Princess & Her Pup." Also in the pic? A dress that maybe wasn't all that appropriate for sharing children's stories.