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.