Times Kimberly Guilfoyle Tried To Look Professional But Failed Miserably

Kimberly Guilfoyle has been in the public eye for decades. With her experience, you'd think she'd learn how to dress her best when in front of the camera. However, the U.S. Ambassador to Greece has racked up just as many fashion misses as she has wins, if not more. Even moments where Guilfoyle attempted to class up her inappropriate style were total failures. She put in similar effort on the occasions where she tried to come off more professional. 

Some of these outfits should've been difficult to sabotage. But Guilfoyle demonstrated that there's a fine line between dressing professionally and being tacky. Unfortunately for the former "Five" host, it's clear that the line is thinner for her than it would be for most. It didn't help that Guilfoyle seemingly tried to stand out in these failed attempts by looking both fashionable and all-business. Although she most likely got a few eyeballs on her when she wore these 'fits, we bet it wasn't for the right reasons.

Kimberly Guilfoyle once hosted "The Five" in a leg-baring dark dress and matching high heels that she tried to pass off as professional. Her plan might've worked if she hadn't been sitting next to her far more modestly dressed co-hosts. Even Dana Perino, who wore a sophisticated but simple red turtle neck, was dressed far more conservatively than the California native. Her peers' classy style made Guilfoyle's 'fit look so unprofessional in comparison that we wonder if her co-hosts did so intentionally, if only to teach Guilfoyle a lesson in business etiquette.

Kimberly Guilfoyle posted an Instagram picture of herself with her son, Ronan Villency, and almost-stepson, Donnie Trump, during their visit on Capitol Hill. She was summoned there by the Senate Foreign Relations Committee to testify for her confirmation hearing as the U.S. Ambassador to Greece. However, her wardrobe came overprepared for the assignment. Although her black pantsuit was fine, the white blouse she had on seemed too large for the rest of her garb. Additionally, the shirt didn't look tucked in all the way, which gave the entire outfit a somewhat sloppy look that could've easily been avoided.

Kimberly Guilfoyle certainly dressed up for the Impact Wealth Magazine cover party with dermatologist and author Nicholas Perricone. The pair are seen smiling next to each other in a picture that Perricone published on his Instagram, but it was hard not to think about the time Guilfoyle went Barbiecore when looking at the clothes she wore in the photo. While holding onto Perricone's book, Guilfoyle sported a short pink dress that we're sure looked more professional in her mind than it did in real life. 

While attending the Republican National Convention on its third day, Kimberly Guilfoyle wore a red dress that could've been one of her most professional outfits if it wasn't so confusing to look at. The upper half of the dress made it look like Guilfoyle was wearing more than one shirt. It somehow got worse when Guilfoyle turned around. From behind, the dress seemed as though it was put on backwards. But it's possible Guilfoyle recognized the fashion mistake, since she hasn't revisited the capelet style since.

Kimberly Guilfoyle reminded us that she was yet another woman in Donald Trump's inner circle who looked like Melania Trump in this photo she posted on Instagram in honor of presidents' day. However, her dress not only made Guilfoyle resemble the first lady even more, but could've easily given the impression that she and the real-estate mogul were enjoying a date. She sported a form-fitting and leggy black frock with tight long sleeves that was more casual than professional. Additionally, the style didn't really match the patriotic message Guilfoyle was going for.

Kimberly Guilfoyle sported a bright orange dress while sitting next to her then-boyfriend Donald Trump Jr. while broadcasting for CPAC. Although she seemed to make an honest effort to dress professionally, the sleeves tarnished the outfit's look. The sleeves looked split open and comically large compared to the rest of the dress. We're not sure if Guilfoyle just decided to roll her sleeves up, or if the dress was designed with the flaw. Either way, it took away all the class and potential from what was almost a very sophisticated look.