Kimberly Guilfoyle Looks Unrecognizable with Her Blonde Bob Hair in the Early 2000s

Kimberly Guilfoyle, a name often associated with political commentary, high-profile relationships, and bold public appearances, shocked many fans when she debuted a blonde bob at a Halloween event in 2008. Known for her signature dark brown hair, the transformation was a striking departure from her usual look. The former Fox News host stepped out with the short blonde hairstyle, complete with bangs grazing her eyebrows, for Animal Fair Magazine's 8th Annual Halloween Pet Costume Party.

As per The List, while her furry companion donned an orange pumpkin-like costume, Guilfoyle paired her daring wig with a navy dress and matching jewelry, making her look completely unrecognizable. The blonde bob immediately drew comparisons to Drew Barrymore’s look in the opening scene of Scream, though her overall outfit suggested a more generic ‘Blonde Kimberly’ rather than a specific character. This bold, temporary hairstyle still stands as one of Guilfoyle’s most surprising beauty moments, cementing her as a figure unafraid of dramatic transformations. Fast forward to today, Guilfoyle remains a polarizing figure in the public eye.

As the fiancée of Donald Trump Jr. and a former spouse to California Governor Gavin Newsom, her personal and political affiliations have kept her in the spotlight. However, it’s not just relationships that accumulated attention—her evolving appearance has fueled rumors of plastic surgery. While Guilfoyle has not confirmed any cosmetic enhancements, experts have speculated about potential cheek and lip fillers.

As per reports, before her rise in conservative politics and her association with the Trump family, Guilfoyle was part of a different world altogether—modeling. A while ago, fans were taken aback when she shared black-and-white throwback photos from her modeling days. In one image, she posed with a vintage car, flaunting pin-up style clothing and a sultry pout. The image nudged surprised reactions from fans, many of whom struggled to reconcile the glamorous model with the staunch political figure she is today. Guilfoyle hasn’t shied away from her modeling past. In interviews, she has reflected fondly on this phase of her life, crediting it as a stepping stone toward funding her law school education.

She remarked, “I knew I wanted to go to law school, and I wanted to have the funds to do so, so when I was in college at UC Davis, I had three jobs: I was working at the district attorney's office as an intern, I worked at the clothing store Clothestime, and I was modeling and doing different jobs in and around San Francisco and Sacramento. I was able to meet a tremendous [number] of interesting people through modeling, and I really learned a lot about self-confidence and self-esteem.” She further shared how she has no regrets regarding her past, “I learned how to cue into my own autonomy as a woman. I don't have any regrets about all of the jobs in the different fields that I've worked in.”