Throwback Pics Of Kimberly Guilfoyle & Dana Perino That Prove They Need Some Styling Tips

The anchors and personalities who rotate through the Fox News arena all set out to make their own names for themselves, while also maintaining friendships and working relationships along the way. One such pairing would be the friendship between "America's Newsroom" co-host Dana Perino and embattled conservative party girl, Kimberly Guilfoyle. While there's plenty to know about Guilfoyle, Perino has often kept many secrets to herself, making their friendship all the more odd. However, considering the two spent seven years together on "The Five," they were destined to see each other outside of work at some point.

Of course, Guilfoyle is a notorious fashion nightmare, often sporting inappropriate outfits on the campaign trail for Donald Trump's 2024 presidential campaign. As much as Guilfoyle appeared to annoy everyone within Trump's inner circle, it cannot be denied that she has a captivating presence — one that often inspires those around her to slowly morph into something similar. Case in point: Ivanka Trump recently channeled Guilfoyle in revamping an outdated hair trend. However, it seems that Perino and Guilfoyle might have swapped pointers with each other all too often during their tenure together. In fact, there were several times both Guilfoyle and Perino desperately needed to hire a stylist, and we found the throwback pics to prove it.

In a throwback Facebook post dated March 6, 2015, Dana Perino is seen snuggling up to her "The Five" co-host Kimberly Guilfoyle with a subtle smirk. Whereas Perino looks perfectly fine — mainly because she's only seen from the waist up and could be hiding a fashion disaster that would shock even Guilfoyle — her pal is seen wearing a white leather jacket. At first glance, everything might seem normal here, they both have hair and makeup done well and nothing seems too out of place, but upon reading Perino's caption, the veneer dissipates.

"My white jacket looked better on her than me (doesn't everything!) so Kimberly Guilfoyle is the new owner. Happy birthday, KG!" Perino wrote, before reminding the world that Guilfoyle's birthday was in a few days. First of all, blatantly regifting something is not the classy move Perino thinks it is. Second of all, it's questionable if the leather jacket could even zip up over Guilfoyle's torso. As much as Perino might have been trying to make it appear she's the type of friend who would literally give you the shirt off her back, it seems she's more the kind of person willing to dig out a piece of clothing from the back of her closet and call it a thoughtful gift.

In a Facebook post from 2016, hosts of "The Five" Dana Perino, Eric Bolling, Kimberly Guilfoyle, and Greg Gutfeld are seen posing together before heading into Sean Hannity's radio show. Which could have been a bit awkward for Perino, considering her ongoing feud with Hannity. Perhaps that's why she came dressed for chilly winter weather — to protect herself from the icy glare of Hannity. While none of the hosts are looking perfectly put together in this snap, it does seem that Perino and Guilfoyle are dressed for wildly different climates.

Guilfoyle, in her wrap-inspired skin tight blue dress, has a hemline inching towards summer. A clear contrast from Perino and her puffy coat. In fact, it appears everyone on "The Five" needed a stylist that day, as Gutfeld also appears ready for a blizzard, but Bolling is still putting on his tie. Whereas we don't begrudge Guilfoyle taking the opportunity to show off her killer legs, it is strange that none of these co-hosts can seem to find a sense of cohesion. There's not even a matching accessory to tie in the bunch, making them all appear to be a haphazard gaggle.

During the 2016 presidential campaign, "The Five" hit the road to tour the United States while visitng important events like the Republican National Convention and the corresponding Democratic National Convention. In a post on X, then Twitter, Kimberly Guilfoyle says, "What a week at the [RNC] ... Next stop..Philly!" The corresponding image is of herself and a rare instance of Dana Perino seemingly without makeup. The duo are standing on the steps of the tour bus, both flaunting incredibly strange fashion choices.

While travel is not always conducive to wearing elaborate fashion pieces, and many are stuck in a battle between style and comfort, there's still quite a bit Guilfoyle and Perino get wrong here. For starters, nothing is tailored properly. Guilfoyle's white zip-up is aiming for athleisure, but she's fallen for those hideous thumbholes, making the sleeves appear overly long and most likely constantly dirty. Perino's whole look, however, is a hot mess express. The army-inspired jacket has confounding sleeves, billowing out to swallow Perino's tiny frame. Her red shirt clashes with the muted green jacket, and with her bold choice not to tuck in her shirt, it drapes well past her hips, making her appear shorter than she already is. Hopefully they stopped by a stylist on their way to Philadelphia. 

In January of 2017, Kimberly Guilfoyle and Dana Perino took to Madison Square Garden to cover the Professional Bull Riders league competition for "The Five." According to Guilfoyle's post on X, she and Perino were "Cowgirls for the night!" Both donned hats for the occasion, as well as all-black attire, which is not necessarily common for rodeos or bull riders. In fact, Perino's choice to wear black pleather pants could have come across as a giant faux pas, as real cowgirls wear denim with leather chaps on top.

While it's clear that neither woman knew how to dress for the occasion, Guilfoyle at least got closer to the authenticity mark. With her cowboy hat she paired a leather jacket — more appropriate than fake leather pants — and a giant belt buckle. However, since belt buckles are a sign of status and often representative of previous competitions won, and it's certain Guilfoyle is not a rodeo queen, the accessory could have been perceived as a major misstep by other attendees. Unfortunately, this means her styling here could still be one of Guilfoyle's worst pre-Trump outfits.

In a 2017 Facebook post, Dana Perino thanks "Kimberly Guilfoyle & Kevin Post for making the trip tonight to [South Carolina]" for an event that she referred to as, "good food, great music, amazing friends." While that sentiment might have been true, the accompanying photo shows that Perino and Guilfoyle can't seem to let go of some out of date fashion trends.

Of course Guilfoyle has worn plenty of outdated outfits during her time, but even for 2017, the skinny jean trend had long been dusty. Pairing her skin tight jeans with pumps is cute, but the zipper decals on Guilfoyle's thighs are distracting and make the whole outfit appear cheap. Plus, the billowy top she's paired the look with doesn't match the rest of the fit, making the whole thing come off as incongruent.

For her part, Perino jazzed up her petite posture with a set of cute heels, but her whole white outfit is such a stark contrast to Guilfoyle's dark ensemble, it clashes. White denim is always a bold choice, especially for an outdoor event. Plus, Perino has once again opted not to tuck in her shirt, making her legs appear shorter than they truly are. Now that Perino's been out of the White House for over a decade, it might be time to invest in a stylist to update her look for the modern era and leave these throwback pictures in the past.