Kimberly Guilfoyle's Look Completely Changes When She Ditches Her Hair Extensions

After rising to global fame through her relationship with ex Donald Trump Jr., Kimberly Guilfoyle has come to be associated with a certain look. Her aesthetic is so strong and identifiable that it's often louder than the other parts of the media personality's life. People might not know that Donald Trump nominated Guilfoyle as the U.S. ambassador to Greece in 2024, but they can definitely describe her look without a reference photo, including heavy makeup, form-fitting outfits, and Rapunzel-like hair extensions. Guilfoyle's lengthy mane has come to be one of most recognizable parts of her look, so the thought of her with short hair is difficult to imagine. But no imagination is needed since we've got receipts from an earlier era of Guilfoyle's life before she fell in love with extensions.

Kimberly Guilfoyle has been through a total transformation over the years, and her brush with shorter hair came in the early noughties, when she was married to then-San Francisco mayor Gavin Newsom. Throughout the Y2K period, Guilfoyle — a graduate of the University of San Francisco Law School herself — kept her hair around shoulder length, occasionally letting it graze her collarbone. And while long hair is seen as a symbol of beauty in many cultures and it's easier than you might think to seamlessly blend clip-in extensions into short hair, we feel the cropped style actually works better for Guilfoyle than all that length.

When done right, a haircut can leave you feeling like dead weight has been removed from your life. That fresh, light feeling is infectious, translating to a natural radiance that can't be faked, and that's what we see when looking at photos of Kimberly Guilfoyle without her extensions. She occasionally varied the style of her hair when she went through this shorter phase, opting for a side part with layers and warm highlights in 2004 while attending a fundraiser in New York City. Two years later at Olympus Fashion Week (a former name for New York Fashion Week), her shoulder-length locks were a darker brown, and while she still had choppy layers, she had a less rigidly defined part line that gave the 'do an even breezier feel. 

Granted, Guilfoyle was 20 years younger in these pics, and her makeup was far less heavy (some even argue that Kimberly Guilfoyle's go-to eyeliner look is completely outdated nowadays), which both contribute to the fresher look. But even if she went for hair at this shorter length today, it could completely transform her style. 

Now, for more looks back through hair history, here are a few more celebs who look totally different without their hair extensions.