Kimberly Guilfoyle is widely recognized for her signature glamorous style, which includes bold makeup, fitted outfits, and her famously long, voluminous hair. While her political career and personal life — including her relationship with Donald Trump Jr. and a 2024 ambassador nomination — have made headlines, it’s her distinct appearance that most people recall instantly. One of the most striking elements of her look has always been her flowing, Rapunzel-like extensions, making it hard to picture her with a shorter hairstyle. However, earlier in her life, before she embraced the extra length, Guilfoyle actually sported a much more cropped cut.
Back in the early 2000s, when she was married to then-San Francisco mayor Gavin Newsom, Guilfoyle’s hair typically fell just to her shoulders or slightly below. A graduate of the University of San Francisco School of Law, she often wore her natural length without the added volume of extensions. Although many cultures associate long hair with beauty, and modern hairpieces can blend flawlessly with shorter locks, the shoulder-length style seemed to give her a more balanced and refreshing look.
Shorter hair often has the power to completely refresh a person’s image, and for Guilfoyle, it appeared to bring a lighter, more vibrant feel. Photos from that time show her experimenting with different variations of the style. At a 2004 New York City fundraiser, she wore warm-toned highlights with a side part and layered ends. By 2006, at Olympus Fashion Week, she had switched to a darker brown shade with choppy layers and a softer, less structured part that gave her hairstyle an easy, effortless vibe.
Of course, being two decades younger and wearing softer, more natural makeup contributed to her youthful glow during that period. Some observers even suggest her current heavy eyeliner style feels dated compared to those earlier looks. Still, a return to a similar shoulder-length cut today could dramatically alter and freshen her overall appearance.
And for those fascinated by hair makeovers, there are many other celebrities who look almost unrecognizable when they swap out their signature extensions for a shorter style.
