Kimberly Guilfoyle's Most Inappropriate Outfits Yet

If there's one thing you can say about Kimberly Guilfoyle's 'fits, it's that they're eye-catching, but not always in a good way. The conservative television personality is known for wearing body-hugging dresses with tons of bling, but she didn't always dress that way. In 2016, Guilfoyle shared pics of herself in a modest LBD with silver detailing on the back. "In love with my new Taoray Wang dress!! Professional, but sleek.. The perfect combo!" she posted on Facebook. Over the years, however, the former Fox News host's style became gaudier and it's clear she loves being in the spotlight.

Guilfoyle has been making headlines as Donald Trump Jr.'s fiancée, but it looks like the relationship is over, and it could be due to her inappropriate fashion. "Don Jr. has been telling people for months that Kim is so uptight and always dresses so professionally in these kinds of dresses and high heels, and never looks relaxed or casual. The tight dresses need to go and she has been told that," a source told People. Judging from her recent outfits, Guilfoyle didn't heed his advice and unfortunately, some of these bas choices have been going on for years.

Kimberly Guilfoyle is no stranger to public speaking so she should have known how to dress appropriately for the 2020 Republican National Convention. Although there was no live audience at the time due to the COVID-19 pandemic, her speech was recorded for millions to see. While red was an appropriate choice due to her repping the Republicans, the cleavage-baring bodice was not. She looked more ready to shimmy during cocktail hour than yell into the microphone about liberty.

Red was Guilfoyle's color of choice again for the 2024 RNC in July , but she was dressed much more conservatively in a crew-neck sheath. Perhaps she got the memo that political events required more demure attire, although her makeup was anything but.

The entire Trump family has made some of the biggest makeup mistakes over the years but Guilfoyle's stamped-on eyebrows, her thick set of falsies, and unblended eyeshadow really took the cake. "More mascara, Kimberly! We can still see a bit of your eyes," a viewer joked on footage of the RNC posted by WSJ News.

Kimberly Guilfoyle made one of her biggest fashion faux pas when she stepped out in a black knit dress for the Zang Toi fashion show in February 2019. While many may think that dark colors aren't see-through, Guilfoyle proved them wrong when flash photography revealed too much. The "Making the Case: How to Be Your Own Best Advocate" author looked blissfully unaware as she posed for the pics and thankfully, she didn't make the choice to go sans underwear.

Guilfoyle should have done a test run photoshoot before she left the house but it appears she has no regrets over her transparent 'fit. In fact, she inadvertently made a pun about it when she posted her OOTD on Instagram and wrote, "Flashback Friday to an incredible NYFW with amazing designers who love America." As her date, Donald Trump Jr. could have given her a heads-up about her dress, or at least lent her his jacket, which would have been a casual way to style her little black dress.

In what has to be one of her most daring looks yet, Kimberly Guilfoyle showed up to Abraham Hamadeh's fundraising event at Mar-a-Lago wearing a tight black dress with a plunging neckline and thigh-high slit. The sheath featured mesh detailing along the chest and thigh which did nothing to make the look more modest. Adding to Guilfoyle's Las Vegas look was her big, blown-out Texas hair, which was one of the biggest hair trends of 2024, and her signature dramatic smokey eyes.

When Guilfoyle shared a reel on Facebook of her introducing Hamadeh in front of the crowd, a fan replied, "She shouldn't dress like that at a fundraiser. I like her but that wasn't appropriate. She should have dressed business attired." Another ranted, "COME ON Kimberly Guilfoyle ........ what would Melania have worn? Show off all you want but does the word 'appropriate' or 'classy' come to mind????" One critic wrote on her Instagram post, "Not campaign appropriate. Perhaps late night disco."

Donald Trump Jr. wasn't kidding when he allegedly complained that Kimberly Guilfoyle could never go casual. In a May 2022 Instagram post promoting Good Ranchers, the mom of one is seen cooking some steaks on her indoor grill while wearing a navy-blue maxi dress and wedge sandals. Of course, her hair was perfectly blown out and she had on a full face of makeup, showing fans that's her typical barbecuing look. Not only was it unsanitary to cook with loose hair, but her tresses could have caught fire at any moment. A few months later, Guilfoyle touted the meat subscription company on her Instagram feed again wearing the same 'fit and a fan quipped, "Nothing says a day at the grill like a badly done smoky eye."

Guilfoyle got dressed up again just to grill some lamb at home as shared in a September 2024 post. This time, she wore a strapless floral dress with a thigh-high slit and a pair of platform heels. It was a brave choice as she didn't even don a cooking apron while making the meal. A fan joked, "That's exactly what I look like when I cook! Thanks for sharing the recipe. Can't wait to try!"

Everyone knows that Donald Trump Jr. loves to hunt and Kimberly Guilfoyle often accompanied him. However, it seems she didn't get the memo that one is supposed to blend in with nature and not wear bright clothes. In a 2018 Instagram post, she is seen posing next to her then-boyfriend and fellow politician Kevin McCarthy. While the two men were dressed casually in muted colors, Guilfoyle looked ready to walk the runway in a bright-white jacket and shiny purple leggings. Whatever they were hunting would have seen them from a mile away.

In July 2020, Guilfoyle shared another sporting picture with Trump Jr. and she was just as colorfully dressed in a multi-colored animal-print vest. It's unclear why she had to go full-glam with her beat face but she's one of the many Trump women rarely seen without makeup. Even in the wild, Guilfoyle is always ready for a photo-op.