Kimberly Guilfoyle's Worst Outfits Of 2025 So Far, Ranked

Compared to other Republican media personalities, Kimberly Guilfoyle has arguably undergone one of the most drastic style transformations over the course of her career. Once known for her nerdy-chic looks, the former First Lady of San Francisco has leaned into an American beauty queen sense of style, complete with fashion and makeup mistakes we're begging Guilfoyle to ditch. From excessive makeup and hair extensions to club wear at formal events, the diplomat's sense of style has been the target of much criticism.

In 2024, Kimberly Guilfoyle wore a few outfits that completely missed the mark, but in 2025, things didn't seem to get any better. By analyzing Guilfoyle's 2025 outfits — sourced from her own and others' social media, as well as major public events — we evaluated her best and worst looks from a vast collection of photos. While we love her bright, red pantsuits for their strong "Legally Blonde" vibes, we can't help but feel the rest of her wardrobe was lacking. Since January 2025, the U.S. ambassador to Greece has failed to dress appropriately for classy events, embraced trends that were at least four centuries out of date, and even wore clothes that resembled Halloween costumes.

At first glance, it may seem like the black dress and black blazer combo that Kimberly Guilfoyle wore to an Amazon-themed restaurant in Monte Carlo was not such a poor choice of attire. The pieces were flattering on her figure, and the long cut was unusually elegant compared to her typical cocktail dresses. However, black was not necessarily appropriate for summer on the French Riviera, where pastels and champagne shades reign. We would loved to have seen Guilfoyle in something like a loose pink dress worn by the likes of society queen Tatiana Casiraghi.

When she was sworn in as the next American ambassador to Greece on September 30, 2025, Kimberly Guilfoyle sported a white, monochromatic pantsuit. While she looked great, her outfit would have been more appropriate at a civil wedding ceremony rather than a professional event. Here, we would preferred to have seen Guilfoyle in a more textured tweed blazer and a pair of stylish heels.

In March 2025, Kimberly Guilfoyle celebrated her 56th birthday with a party and a head-turning outfit. In a sparkling gold, one-sleeve cocktail dress and a pair of matching metallic shoes, the public figure seemed ready to shine. The only problem? The one-sleeve style can be very hit or miss as it goes in and out of fashion regularly. Guilfoyle might have chosen something more classic, like a sweetheart strapless neckline or an off-the-shoulder look.

Dr. Nicholas Perricone posted a photograph of Kimberly Guilfoyle on Instagram in April 2025. In the shot, Guilfoyle was dressed in a bubble-gum pink mini dress and clutching Perricone's book, "The Beauty Molecule." Bubble gum is a great shade but generally needs to be paired with a neutral brown or gray to capture a sense of elegance. Here, Guilfoyle matched the color with — drumroll please! — more bubble-gum pink, as seen on the sparkly cuffs adorning her outfit. The combo was simply too noisy to be considered fashionable.

On Mother's Day 2025, Kimberly Guilfoyle wore a pink mini dress with a white collar that gave us antique doll vibes. Not only that, but the style of the frock paired with the girlish pink, resembled a little girl's dress as opposed to the 50-something-year-old mother of an adult child.

On Kimberly Guilfoyle's son, Ronan Villency's, birthday, the public figure took to Instagram to celebrate the special occasion. However, the outfit she wore in the first slide of the post was very disorienting. Her navy sheath dress had a sweetheart neckline that was decorated with navy lace. The whole thing culminated in a Peter Pan collar that created the impression of two separate necklines. When it comes to fashion, less is more. A simple sheath dress would have been great for the occasion.

When GB News' U.S. division launched in Washington D.C., Kimberly Guilfoyle seemed supportive of the move, even describing it as "such a special night" on Instagram. Despite this enthusiasm, the media personality did not exactly dress to the nines. She appeared at the event in a leather black jacket and a pair of black slacks. Meanwhile, photos show that her colleagues dressed more formally in suits and ties. Generally, it's considered better to be overdressed than underdressed, and here, Guilfoyle would have improved her look by wearing a nice blazer.

In celebration of some friends' 10th wedding anniversary, Kimberly Guilfoyle headed to the Florida Keys. Photos of the event hinted at an all-white dress code, which Guilfoyle embraced in a short cocktail dress with a plunging V-neck and cutouts. Given that color dress codes are usually enforced to prevent any one guest from standing out, Guilfoyle's revealing outfit was not the vibe. Something longer and airier would have been stunning.

Kimberly Guilfoyle has worn her fair share of outdated outfits, but the look she selected for her meeting with U.S. Secretary of War Pete Hegseth in October 2025, took the cake. On this occasion, she sported a black vest with black trousers and a white blouse with a massive pussy bow down the front. Guilfoyle's clothing looked strikingly similar to aristocratic men's fashion in 17th-century France. To complete her look, she could have accessorized it with a feathered hat and a sword!

Fashion mistakes are inevitable, but making the same mistake twice is not. In 2025, Kimberly Guilfoyle embraced the outdated 17th-century French men's blouse on multiple occasions. When meeting with top officials that October, she paired the frilly, pussy-bow blouse with a lavender suit and matching lavender heels. Arguably, this made her look even more out of date, as vibrant colors were quite popular in the court of French king Louis XIV.

Did you think Kimberly Guilfoyle's Baroque frills couldn't get worse? Think again. When meeting with Doug Burgum, Guilfoyle wore her favorite 17th-century blouse and blazer combo, but in the wrong size. Her blazer lacked basic tailoring, with the sleeves drooping halfway down her hands. The shoulders were also a tad too wide, leaving Guilfoyle looking like she was swimming in her own clothes. Even the wide-legged pants were not tailored to her frame, as they appeared even larger than Burgum's.

Nothing says "summer on the French Riviera" like ... fur? Well, according to Kimberly Guilfoyle, the nautical attire that has long reigned summers in Provence and Monaco should be thrown to the wind and replaced with large furry cover-ups. Indeed, in the summer of 2025, she was spotted port-side wearing a lacy black dress and a monstrous faux fur coat. The real shame here is that her dress was actually very trendy in France this summer. She could have accessorized it with an oversized blazer to fit the regional vibe.

It's hard to say precisely where this furry pink coat would be considered appropriate, but it certainly was not at the Italian wedding that Kimberly Guilfoyle mentioned in her Instagram caption. A quick peek into the background of the shot shows other guests wearing elegant and understated attire. To fit the aesthetic, Guilfoyle could have gone with one of Coco Chanel's little black dresses.

If impersonating a vampire is a bad thing, Kimberly Guilfoyle does not seem to know it. At Gala Cannes 2025, the media personality dressed in a scarlet gown with puffs on the sleeves and red lace that lined her chest and legs. In the old-timey yet overtly sexy red dress, Guilfoyle looked like she'd wandered off the set of the "Twilight" movies. Per Vogue France, the best looks at the Cannes Film Festival that year were more subtle, with sheer lace being applauded on otherwise classic black dresses — certainly not red ones.

In the summer, Kimberly Guilfoyle attended the Monaco Grand Prix. Princess Charlene of Monaco wore a modest red blouse and matching slacks, and her niece by marriage, Tatiana Casiraghi, wore a flowing floral frock. Kimberly Guilfoyle wore a cheaply made outfit that looked like it belonged on a college student at a music festival. Sporting her Grand Prix pass, a bandeau, a cheap skirt, and a blazer, Guilfoyle did not match the upscale energy of the event. A pale linen dress, straw hat, and gold necklace would have been perfect here.

There's a fundamental difference between wearing nude and letting nude wear you. Kimberly Guilfoyle has, unfortunately, not always grasped this delicate balance. Following an August 2025 ladies' event, Guilfoyle's friend, Daphne Barak, took to Instagram with a photo of their get-together. In a nude sweater dress with matching heels, Guilfoyle looked rather nude herself — not to mention barefoot. The secret to pulling off this tricky shade is to select a tone that's quite different from one's skin color. A bright peach would have been preferable here.

If there's ever a dress that makes the wearer look naked, it's probably a dress that resembles underwear. At a 2025 Mar-a-Lago party, Guilfoyle wore what was essentially a corset with a skirt. The fact that this outfit was, indeed, a dress, seems like a mere technicality. The piece's plunging neckline, sheer lace bodice, and high shoulders looked straight from the lingerie store. While we love lingerie, the trick is to generally wear it beneath one's clothes and not attached to a feather skirt.