Kimberly Guilfoyle's Old Updos Have Us Almost Thankful For Her Mile-Long Hair Extensions

When most people think of Kimberly Guilfoyle, they likely picture the ambassador with a face full of cakey makeup and long brown hair extensions. But it turns out this wasn't always her go-to style. Years earlier, Guilfoyle was a chic model with short brown hair, and on occasion, she wore her hair up. 

While having variety in your personal style is almost always a good thing, in Guilfoyle's case, there's a clear reason why she wore her hair up one day and seemed to never don the style ever again. Her updos really could have used some work, and although she tried, she never quite figured out what hairdos best suited her, aside from long, wavy hair worn down.

Guilfoyle was much more willing to experiment with her style when she was pursuing a law degree and modeling to cover her college costs, as well as in her early days working as a lawyer and then media personality. She had an arguably more elegant and sophisticated wardrobe than she does now, but that style definitely didn't extend to her hair. Check out a few of the rare instances when Guilfoyle attempted to rock an updo and it didn't go so well.

Back in the 2000s, Kimberly Guilfoyle wasn't afraid to try different updos, for better or for worse. During an appearance at an NYC screening of the Bob Dylan biopic movie "I'm Not There" in 2007, she went for an all-black outfit — a simple look that could feel chic with the right hairstyle and accessories. Unfortunately, Guilfoyle didn't have these. 

Her dark brown hair was parted to the side and pulled back with a few wispy pieces hanging out around her ears. While the hairstyle might have worked with other outfits, it only made her ensemble give off office assistant vibes, and that definitely wasn't what she was going for.

In 2006, the young lawyer went for a more glam ensemble for a special party in NYC benefitting the Whitney Museum of American Art's Independent Study Program. For the event, Kimberly Guilfoyle wore a chic white dress with a matching shawl over her shoulders, but her hairstyle wasn't a good match. 

The hairdo made Guilfoyle appear much older than her age, and the side part didn't suit her face. Sure, having her hair in an updo could have done a better job of showing off her dress and accessories than wearing it down, but it ended up being more distracting instead.

When Kimberly Guilfoyle was still married to Gavin Newsom, the then-mayor of San Francisco, she attended the 15th Annual GLAAD Media Awards in San Francisco, California, on June 5, 2004. For the event, Guilfoyle went for another rare updo, switching it up a bit this time.

Her hair was held back by a clip or something similar in a messy style with a bit of volume on the top. While it was certainly better than the sleek looks she tried before, it was only a marginal improvement. 

Another event, another swept-back hairstyle. This seemed to be Kimberly Guilfoyle's motto in the 2000s, especially for formal events. In late 2007, she attended the New Yorkers for Children Annual Fall Gala in New York City. She was accompanied by her second husband, Eric Villency, whom she married in May 2006 after divorcing Gavin Newsom. 

While the black dress she wore to the gala was fitting for the formal night, with an elegant square neckline and ruffle detailing, the hair wasn't a good fit. In fact, from most angles, the hairstyle made her look like she had a pixie cut, rather than her actual long hair. 

Only a couple of months after the couple tied the knot, Kimberly Guilfoyle and Eric Villency were photographed walking around Soho in New York City, looking like the everyday casual couple. At the time, Guilfoyle was pregnant with their son, Ronan, and she wore a relaxed white dress for the outing.

To go with the dress and flip-flops on her feet, Guilfoyle seemed to carelessly put her hair up in a big white clip. Although the style can work for some people, it didn't work for her, especially when her hair started blowing in the wind, causing pieces to fall out and fly around.

Years later, when Kimberly Guilfoyle was working at Fox News as a TV personality, she took a trip down memory lane on Instagram and shared some old modeling snaps with fans. In one photo posted in 2015, a young Guilfoyle modeled what seemed to be a bra, with her hair piled on top of her head.

Along with the big mass at the top, the hairdo also had a bunch of stray strands floating around her face. It all looked quite a bit like a messy mop, proving that even model hairstylists didn't know how to create a flattering updo for Guilfoyle.

During a vacation to Palm Beach, Florida, Kimberly Guilfoyle shared a selfie on Instagram of herself at a resort, with a pool and the beach in the background. In the image, Guilfoyle had her hair in a low ponytail, an especially rare style for her. 

The side part and the thick ponytail hanging over her shoulder just didn't complement her face shape and makeup. It's likely that Guilfoyle didn't like the style on herself either, as there are few to no photographs of her trying it again after.