Rare Pics Of Kimberly Guilfoyle Rocking Casual Outfits

When it comes to dressing to the nines, you can always count on Kimberly Guilfoyle to deliver. Granted, Guilfoyle has a long list of outfits that are beyond tacky, but considering her penchant for embellishments like feathers, sparkles, and sequins, tastefully sophisticated styles just aren't in her DNA. Which is more than okay. After all, not everyone can have the fashion sense and style of Princess Diana.

But because Guilfoyle loves to get dressed up, it's pretty darn rare to find her rocking casual outfits. In fact, according to People, Don Jr. had been complaining about Guilfoyle's attire months before the two even broke up. "Kim is so uptight and always dresses so professionally in these kinds of dresses and high heels, and never looks relaxed or casual," said the source. Then when the two did split, Guilfoyle doubled down on her sense of style, parading around in a series of outfits that screamed revenge — also proving Don Jr.'s point.

However, Guilfoyle is able to dress down when the occasion calls for it. And, somewhat surprisingly, actually looks good when she does. If you thought Guilfoyle's wardrobe was a sea of tight mini dresses and bedazzled items, well, you're right. But amongst that, likely tucked in the far corners of her closet, are a handful of items that are 100% casual and relaxed.

In October 2022, Kimberly Guilfoyle posted a photo of herself, Don Jr, and her son, Ronan, in front of a Camp David sign. In it, all three are dressed for a day hike, with Guilfoyle wearing athletic pants, sneakers, a puffy jacket, and a knit hat with a pom-pom. While the post was meant to celebrate Ronan's 16^th birthday, based on the caption, it's Guilfoyle who steals the show. Without the gaudy dress style that Guilfoyle can't let go of in sight, it's hard to believe it's really Kim.

If you never thought you'd live to see the day when Kimberly Guilfoyle is holding a baby pig at a farm while wearing a flannel shirt, you're definitely not alone. However, as evidenced here, it has happened — at least once. While we don't know if this flannel is borrowed from Don Jr. or if it actually belongs to Guilfoyle, we do know that on Memorial Day in May 2020, Guilfoyle cozied up with some adorable piglets and looked pretty at home while doing so.

In August 2020, Kimberly Guilfoyle posted a photo of herself on X watching Don Jr. promote his book "Liberal Privilege: Joe Biden and the Democrats' Defense" on Fox News. Not only is Guilfoyle dressed super-down, wearing a hooded top covered in different sized stars, but she even appears to have temporarily given up the makeup trend we've been begging her to ditch: dark smokey eyes. Guilfoyle looks so proud of her partner that you almost want to hope their relationship will be able to weather the next few years.

Throughout the summer of 2020, despite the world being on lockdown due to the COVID pandemic, Kimberly Guilfoyle was out on the road (and amongst the virus) campaigning tirelessly for Trump. Although Guilfoyle's Inauguration looks are some of her most questionable to date, here she managed to pull off both casual and cool. While she's clearly unable to leave the glitz totally behind, as we can see with the bedazzled belt she's wearing, the rest of the outfit is serving up a relaxed and confident vibe.

In January 2020, Kimberly Guilfoyle and her son, Ronan, posed in front of a US Air Force plane. While not as casual as we've seen her, Guilfoyle is still very casual compared to what she usually wears. Guilfoyle paired tight black pants with a matching black shirt and jacket. Although not completely void of makeup, again, compared to what we've come to expect from Guilfoyle, her face is practically bare. When the heavy makeup is removed, it gives Guilfoyle a softened look. 

Similar to her now-ex, Don Jr, Kimberly Guilfoyle's Instagram has proven that she also likes to kill innocent animals for sport. For Don Jr's son Spencer's seventh birthday in October 2019, the couple left the other kids at home and took Spencer fishing and hunting in Utah. Naturally, because you simply can't do those things in frilly dresses and five-inch heels, Guilfoyle dressed perfectly for the occasion. While her outfit screamed casual outdoor fun, her nails and makeup proved that where Guilfoyle can add a dash of her brand of glamour, she absolutely will.

In November 2017, long before MAGA tried to push the narrative that Tylenol causes autism, Kimberly Guilfoyle was an advocate for the awareness and acceptance of autism, as well as inclusivity for those who are autistic. Here, Guilfoyle poses alongside former American football player Tiki Barber, while rocking tight black pants, knee-high riding boots, and a t-shirt that promotes the cause. Guilfoyle's hair is swept to the side in a loose side braid, proving just how nearly unrecognizable she is without her trademark hair extensions.

Although it's not quite clear who crashed this October 2018 hunting party, Kimberly Guilfoyle or Kevin McCarthy, the point is these two, along with Don, Jr. roamed the Montana countryside and had an amazing time, according to Guilfoyle's Instagram post. In addition to wearing a very casual and outdoorsy outfit, some of Guilfoyle's Instagram followers must have been inquiring about where she does her shopping because she listed the brand names of her articles of clothing.

A large western style belt buckle on Kimberly Guilfoyle? You better believe it. In January 2017, Guilfoyle posted this photo of herself with former White House Press Secretary Dana Perino and a cowboy-hat-wearing fella at Madison Square Garden. Considering the location and attire, it must have been a country musician or band that took the stage that night. In addition to the belt buckle, Guilfoyle's choice of black jeans, black turtleneck, and black leather jacket is the perfect casual yet stylish look for such an evening.

In April 2017, someone took this candid photo of she and her son, Ronan, at the airport. According to the caption that accompanied the photo, Guilfoyle was en route to the Army Navy Country Club in Virginia so she could emcee the 5th Annual Purple & Gold Gala. Dressed like most do when they have a long traveling day ahead of them, Guilfoyle is showing off that she's mastered the shabby chic look. It's also worth noting that sans all those layers of makeup, Guilfoyle looks refreshed and down to earth. This is probably why she posted this candid moment.