Kimberly Guilfoyle's Rare Makeup-Free Throwback Shows A Natural Beauty
Over time, Kimberly Guilfoyle's signature aesthetic has come to include a mountain of hair extensions and lots of dark eye makeup. Guilfoyle's style transformation to this look accelerated during her relationship with Donald Trump Jr. However, it wasn't always this way. Previously, Guilfoyle's makeup strategy was a lot more understated. Sometimes, she even ditched the products altogether. Every once in a while, Guilfoyle reminds us of her previously more laid-back style, like when she posted a series of vintage pics on Instagram with her son, Ronan Anthony Villency.
Here, Guilfoyle's long hair looks great without the unneeded pouffiness of extensions. Sans makeup, her skin is glowing, and her eyes look amazing. Without a ring of heavy eyeliner, they also look larger. Guilfoyle's Instagram followers were also enthusiastic about her makeup-free face. "You are gorgeous 'au naturel'!!!!" gushed one fan. Guilfoyle was visiting Ronan at summer camp, and her no-fuss beauty regime was a perfect choice. All she needed is a layer of sunscreen to protect her skin as she spent time with her son.
Although Guilfoyle doesn't provide a date for the pics, the photo appears to be from just before a pivotal time in the evolution of her approach to cosmetics. Villency was born in 2006. Based on his height, he's maybe around eight or nine years old, so this photo could be from the mid-2010s. Guilfoyle's makeup style completely changed between 2004 and 2024, and around 2016 she really amped up the amount of products she used.
Plastic surgery may have taken a toll on Guilfoyle's natural face
Beyond the addition of copious amounts of makeup, Kimberly Guilfoyle's long been subject to plastic surgery rumors, with some describing her look as a prime example of the "Mar-a-Lago face" trend. By studying photos of Guilfoyle, some believe these purported procedures interfered with her natural beauty. "Look at this cute, beautiful smile," enthused Dr. Jennifer Armstrong on TikTok, referencing an earlier picture of Guilfoyle with minimal makeup. Armstrong contrasted this look with a photo of Guilfoyle's current, more heavily made-up face. She believed excessive filler changed the appearance of Guilfoyle's lips. In addition, Armstrong felt filler had impacted the corners of Guilfoyle's mouth. "They're pushed up too much, and, like, the whole mouth is going up like the Joker."
However, it's hard to get an apples-to-apples comparison, since these newer photos only show Guilfoyle with her current cosmetic style. Retro pics seem to be the only place to glimpse Guilfoyle wearing far less makeup, or even with a bare face. Frequently, these old photos reignite plastic surgery rumors and create a yearning for Guilfoyle's more minimalist beauty routine.
"So beautiful without the heavy make-up," praised one fan on Instagram, after Guilfoyle's 2025 Mother's Day post. One photo featured a no-makeup Guilfoyle snuggling with her newborn son. The carousel included a range of eras, perfect for comparing and contrasting Guilfoyle's evolving style. "You used to be a natural pretty before your horrendous #magamakover," denounced one harsh critic.