The Rare Times We've Seen Kimberly Guilfoyle In Normal Clothes

When it comes to style, Kimberly Guilfoyle likes to go big or go home. The world is used to seeing her decked out in all her glittery finery, and the list of Guilfoyle's inappropriate outfits and flesh-baring fashion felonies is seemingly never-ending — let's just say she's got legs and knows how to flash them. However, Guilfoyle underwent a noticeable style change before her bombshell Donald Trump Jr. split. Sadly, though, it appears that it was just too little too late to save the Donberly romance.

According to reports, Guilfoyle's inappropriate outfits had already reportedly landed her on Donald Trump's bad list. And once you make it onto there, the writing is pretty much on the wall. Sure enough, Don Jr., ever desperate in his quest to please his dad, purportedly ditched Guilfoyle for a younger model, Bettina Anderson, whose style is more reminiscent of his stepmom, Melania Trump. "Don Jr. has always wanted to look good in his father's eyes," a source told People in December 2024. "Someone like Bettina, who is and has been a model and is in Waspy circles of Palm Beach, is something that would impress him."

Still, Guilfoyle does occasionally take a breath, lets her hair down, eases up on the eye makeup, steps out of the sky-high heels, and sheds the skin-tight dresses. Admittedly, not often, but it does happen. We're checking out the rare times we've seen Guilfoyle in normal clothes.

Kimberly Guilfoyle ditched her trademark va-va-voom glitzy glam and went full-on Pennsylvania soccer mom when she took to the stage in October 2024. "Great to be in the American heartland with the patriots of Pennsylvania. You are truly the Keystone State!! Your voice & your vote matters more than ever!" she captioned a carousel of pics posted on Instagram showing her, clad in black leggings and a black zip-front fleece, getting down with some pumpkins and Donald Trump Jr.

Guilfoyle's casual clothes are definitely few and far between. That much was evident when she opened her closet doors and invited Us Weekly in for a rummage. The rails were packed to the brim with brightly colored, sparkly dresses that were huge on the frills and short on the hem. Oh, and shoes. Rows and rows and rows of shoes. Wedges, sandals, pumps in clashing colors, and animal prints, with one thing in common: sky-high heels. "Every girl knows you can never have enough closet space. And in New York City, it's like, wow, you need a magic wand to figure it out," a perky Guilfoyle tells the camera.

The video was filmed in November 2017, prior to her great MAGA indoctrination. That much is clear from her jibe while explaining how she managed to jam so much stuff in. "I went painstakingly to try to go ahead and build a wall, better than Trump's I think," Guilfoyle quipped.

Kimberly Guilfoyle wants everybody to know she's back in Washington (for now) and ready to roll. "America is BACK! Celebrating with true patriots as President Trump leads us into the next chapter of greatness," she captioned a carousel of pics on Instagram in January 2025. The photos show her posing with various MAGA cohorts, decked out in all her gaudy glory — with the exception of one rare pic of Guilfoyle in normal clothes. In it, she grins broadly in front of the Capitol building, clad in a white pantsuit, cream pussy bow blouse, and black coat, with Ronan Villency standing proudly beside her.

Since Donald Trump Jr. and Guilfoyle's split, Villency has become his mom's number-one man. And, with his dark features and toothy grin, Guilfoyle's son is growing up to look just like her — albeit with way better dress sense.

After Donald's inauguration, Guilfoyle began gearing up for her big fat Greek adventure. Given her rabble-rousing podium meltdowns, you'd be forgiven for thinking she's a bizarre choice for a diplomacy role. You could also be forgiven for thinking it's a way to ship her out of the country now that she's Don Jr.'s non-grata. But don't cry for Guilfoyle, USA! "Do not feel sorry for her or think she's being pushed off to the side. I'd be far from feeling sorry for her," a source told People in December 2024. "I think she's about to catapult into her next chapter, you know, into the diplomatic world."

Kimberly Guilfoyle is showing off her woke side in a November 2017 Instagram post. The then-Fox News co-host is seen posing for a selection of pics in black jeans, boots, and a T-shirt emblazoned with "Awareness. Acceptance. Inclusion."

The men and women of MAGA were totally there for Guilfoyle's dressed-down style. "Wow Kimberly you're looking good regular street clothes. love it when you come into Chicago to do a book signing," one fan commented on her photos. "Miss Kim you look good in jeans lady," another gushed. "You are my favorite! Love this outfit and all your classy ones on The Five!" a third raved.

It's pretty much impossible to envisage Guilfoyle spreading any such message nowadays, as awareness, acceptance, and inclusion seemingly have no place in the 2025 Trump administration. In fact, Donald has declared an all-out war on the three, passing a number of measures to curtail diversity, equity, inclusion, and accessibility initiatives. Taking it a step further, Trump made the jaw-dropping (and totally baseless) claim that the FAA's efforts to recruit people with "severe intellectual and psychiatric disabilities" contributed to the January 30 crash between a helicopter and passenger jet that resulted in 67 fatalities.

Kimberly Guilfoyle was fresh-faced and ready to fly in January 2020. Clad in a long black crew neck jumper, leggings, and blazer, Guilfoyle, resting her hand on her son Ronan Villency's shoulder, looked like any other regular mom (albeit one who's about to jump on a U.S. Air Force private jet). "My angel. God Bless America," she captioned a pic of the two posted on Instagram.

The social media fashion police were all about Guilfoyle's carefree casual clothing. "Wow love this outfit !!!" one wrote. "I want your pants and top – so chic. Designer?" another asked. "Perfectly elegant. No 'boobage' needed," a third decreed.

Say what you will about Guilfoyle — and there's certainly a lot that's up for discussion — but she's a doting mom by all appearances. "This Mother's Day I'm thinking about how blessed I am and lucky that God gave me my greatest treasure... you Ronan. My mom taught me everything that it means to be an amazing mother and you are my greatest pride and joy," she captioned a selection of family photos on Instagram in May 2020.

On the rare occasions Kimberly Guilfoyle is spotted out and about in normal clothes, she's usually with her son, Ronan Villency. Such was the case in June 2019. "Sunday NFL Flag Football! Go Ronan! Lots of fun and kids from all different schools and ages up to 15. Love that the other team had an awesome girl playing too! Just like when I was the first at my school to play on the all boys soccer team!" she captioned a pic of her, clad in a black T, leggings, jacket, and kicks, standing by her son's side.

"I just wanna see you in those pants!" a follower creeped in the comments. "Nice Sneakers," another wrote. "Kimberly, you can't even stop looking HOT when your at your son's flag football game. Probably wake up smokin. Donald Jr. has to hurry and jump in cold shower to keep from being burned....LOL," a third raved.

Still, she isn't always in modest mom mode. For instance, Guilfoyle's outfit for Villency's prom was one of her most tasteless yet. Which, given the level of competition, is really saying something. She posted photos of the crime against style on Instagram. It comprised a frou-frou lilac mini-dress with giant diamante bows holding the split-to-the-waist plunge neck together and sky-high silver Prada platform sandals.