Political enthusiasts and casual internet users alike were left doing a double-take this week after a series of old photos of Kimberly Guilfoyle resurfaced on Reddit.
The 56-year-old political commentator, known for her glamorous style and high-profile relationships, looked almost unrecognizable in her younger images.
From Political Spotlight to Viral Reddit Sensation
Guilfoyle, famously the ex-fiancée of Donald Trump Jr. and previously married to California Governor Gavin Newsom from 2001 to 2006, has always attracted attention for both her career and her fashion sense.
Over the years, she has made headlines for her polished, professional looks—so much so that, according to People last December, Don Jr. reportedly criticized her for being “uptight” and favoring high heels and tight dresses over a more relaxed style.
The Photos That Left Everyone Stunned
This week, a Reddit user posted a collection of Kimberly’s earlier photos, quickly sending the thread viral.
In one snapshot, she sported a short hairstyle—quite a departure from the signature long locks she’s known for today.
Her bold eyebrows and natural makeup gave her a fresh-faced, modeling-ready appearance.
Another image showed Kimberly with an elegant twisted up-do, light pink lip gloss, minimal makeup, and dangling earrings paired with a black blazer.
The set also included candid shots of the former First Lady of San Francisco out on the town.
In one, she rocked an all-pink ensemble with shimmering makeup, while in another, she wore a spaghetti-strapped black dress and a short haircut, showing off a youthful, effortless charm.
Then and Now: A Striking Transformation
The Reddit post compared these past images with current photos of Guilfoyle, where she is seen with her signature smokey eyes, darkly defined eyebrows, and plumped lips.
Fans were quick to comment on the striking difference.
One user wrote, “Oh wow, if you hadn’t said they’re the same person I would never have believed it.”
Another added, “She gave herself Republican face. What a tragedy,” while a third chimed in, “She was stunning when she was younger.
Unfortunately she lost her marbles and destroyed herself to fit that orange freak’s preference.”
Others reminisced fondly, noting, “Pic two is so pretty” and “She was definitely a looker when she was younger.”
Recent Glamorous Appearances Keep Fans Talking
These viral throwbacks come just months after Guilfoyle appeared on the cover of Metropolitan Palm Beach magazine, wearing a bright red blazer and white blouse with a pussy bow.
The glamorous shoot sparked mixed reactions among her 56-year-old followers, with some praising her style and others accusing her of relying on filters to enhance her appearance.
Fans React to the Transformation
Whether admired for her past natural beauty or critiqued for her current look, Kimberly Guilfoyle continues to captivate the internet.
These resurfaced images serve as a reminder of how much public figures can evolve over time—both in style and in the public eye.