Kimberly Guilfoyle is an American attorney, former prosecutor, and onetime Fox News presenter. She’s also known as the ex-fiancée of Donald Trump Jr. and the subject of persistent plastic surgery speculation.
Photos from 2001 and 2024 highlight a dramatic shift in her appearance, showing how unrecognizable she has become.
Although Guilfoyle has never confirmed undergoing plastic surgery, she hasn’t denied it either, and few credible insider details exist.
Her evolving appearance has drawn widespread attention, beyond heavy makeup. Compared to her early public life, she now looks completely different.
In this dive, we’re breaking down her transformation era by era, from her early legal career to her life in the MAGA spotlight
Early Career, Natural Style (2000-2006)
Black and white portrait of Kimberly Guilfoyle with voluminous hair, showcasing her before and after transformation era.
Before stepping into the political world, a young Kimberly Guilfoyle worked as a model, and her natural beauty was obvious. That clean-cut style stayed with her after law school when she joined the San Francisco district attorney’s office in 2000.
After studying at the University of San Francisco, she transitioned from model to prosecutor with little more than a wardrobe change. Her look remained fresh and low-maintenance, a contrast to her later image.
Guilfoyle’s natural charm likely helped catch the eye of rising politician Gavin Newsom.
Kimberly Guilfoyle in green top holding a cup and newspaper talking to Gavin Newsom holding a coffee in a modern kitchen.
The pair married in 2001, and Guilfoyle became First Lady of San Francisco when Newsom took office as the city’s 42nd mayor in 2004.
They often appeared together at public events, with Guilfoyle wearing minimal makeup, nude lips, and no noticeable cosmetic enhancements.
By the end of this era, her personal life shifted dramatically. She filed for divorce in 2005, finalized it in 2006, then quickly remarried businessman Eric Villency and had her son, Ronan, that same year.
Her look mainly stayed the same through it all, changing only with minor hair and fashion tweaks.
Young Kimberly Guilfoyle smiling at an event, wearing a black top and long beaded necklace showing early era style.
Fox News Image Evolution (2006-2013)
Kimberly Guilfoyle and a man posing indoors with the O’Reilly Factor poster visible in the background.
Kimberly Guilfoyle’s career hit a new high in 2006 when she joined Fox News as the host of The Lineup.
Even after the show was cancelled, she stayed on as a network contributor, and with that came a noticeable shift in her on-screen appearance.
Her makeup became more pronounced, and her hair wore the signature Fox News glam with thick blowouts, high volume, and heavy styling.
Guilfoyle’s face looked subtly different compared to her modeling days, especially her nose, which sparked rumors of a rhinoplasty. The changes were apparent but still mild, whether it was actual surgery or just smart contouring under bright studio lights.
Kimberly Guilfoyle sitting in a studio wearing a red dress, smiling, representing six eras of change before and after.
Things became more evident during her co-hosting of The Five (2011–2018).
Her jawline looked more sculpted than ever. Plastic surgeon Dr. Dennis Schimpf told MSN she likely had a facelift to maintain that tight jawline and offset signs of aging.
Her wardrobe also shifted from conservative to sleek and form-fitting suits and curve-hugging dresses.
Greater Glam and First Procedure Buzz (2014-2018)
Guilfoyle took her glam to the next level in 2014, the year she began hosting Outnumbered. After nearly a decade in TV, her makeup and styling had clearly evolved.
Her face appeared much more sculpted, and the red carpet moments reflected a major transformation.
Kimberly Guilfoyle smiling at an event wearing a black top with white floral patterns, showcasing a before and after transformation.
According to Dr Schimpf , Botox in her forehead and around her eyes likely helped achieve the smoothed-out finish. He also believes Guilfoyle started using fillers to define her cheekbones and sharpen her jawline.
Some speculated that micro-jawline sculpting may have played a role, but Dr. Schimpf suggests ongoing fillers are the more likely explanation.
This is also when the plastic surgery chatter got louder. Guilfoyle’s face seemed to shift slightly with every appearance, especially her lips, which looked fuller over time. The changes were hard to miss.
MAGA Spotlight and RNC Viral Moment (2019-2020)
Kimberly Guilfoyle gained wider attention after she began dating Donald Trump Jr. in 2018, though their relationship wasn’t fully public until the following year.
Once she joined Trump’s 2020 re-election campaign, Guilfoyle entered the MAGA spotlight, and the scrutiny ramped up.
Her most talked-about moment came at the 2020 Republican National Convention, where her fiery speech went viral.
RNC 2020: Kimberly Guilfoyle’s fired-up speech makes waves on social media https://t.co/s4WdwBtyyM pic.twitter.com/srrDFVizcz — New York Post (@nypost) August 25, 2020
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