Kimberly Guilfoyle's Leggy Looks Have Caught Everyone's Attention

Nobody puts Kimberly Guilfoyle in the corner, no matter how much some may want to. Her fiery rhetoric and rabble-rousing, screeching speeches ensure she's always heard. Guilfoyle's wardrobe of inappropriate outfits — a seemingly bottomless well of flimsy, flamboyant, and flesh-flashing crimes against fashion — guarantees she will always be seen. The tighter, gaudier, and shorter, the better for Guilfoyle. Still, although her busty, leggy looks catch everybody's attention, it's not always for the right reasons.

Guilfoyle's outfits are as polarizing as her politics. Some appreciate and applaud her dare-to-bare bravado and dedication to material minimalism. Others? Not so much. Guilfoyle's botched attempt at Nashville chic with a tasteless fringe dress left little to the imagination and failed to impress many. "At first glance, I see Teresa Guidice from Housewives of NJ. Brunettes should soften as they age and blondes go darker," one hater opined.

Then there are Guilfoyle's scandalous Halloween costumes. Sultry, sexy, and oh-so-skimpy, they're sure to get tongues wagging and MAGA men salivating. Still, if one thing's for sure, the former Fox News host definitely prefers hogging the headlines to sitting on the sidelines. From Donberly date night to a plunging pink golf gown, we're checking out some of Guilfoyle's leggy looks that caught everyone's attention.

Kimberly Guilfoyle was decked out in all of her sparkly white glory to enjoy the Miami Admiral's Cover Yacht Club and Marina's end-of-season gala, "Havana Nights." She paired the leggy look with silver, sky-high platform sandals that looked like they were made for dancing, albeit in a gentleman's club rather than a yacht club. "Thank you @admiralscovelife for an amazing evening at Havana Nights!" Guilfoyle captioned a carousel of pics, including her posing by a pool and hanging out with Madison Sohaney and realtor Kimberlie Glaser, among other women.

Guilfoyle's Instagram comments lit up like the Rockefeller Center Christmas tree. "Stunning, Gorgeous, Fabulous, and so smart the whole package!!" a fan gushed. "You are so gorgeous kimberly. God bless you and your loved ones in Jesus name," another conferred. "This just proves beautiful women have beautiful friends," a third raved.

Not surprisingly, both Sohaney and Glaser are fully on board the Trump train. The latter is actually a member of The Trumpettes, while the former is a model, actor, and alleged MAGA muscle enforcer. "Am told that the woman who attempted to unlawfully detain a reporter is named Madison Sohaney," journalist Ben Schreckinger claimed on X, formerly Twitter, in September 2024, referring to Politico writer Adam Wren's unpleasant encounter with an angry female and four threatening men while reporting on a meeting between Mike Davis and Donald Trump Jr.

Kimberly Guilfoyle pulled out the Balmain big guns for a night out with Donald Trump Jr. in June 2024. She wore a black and white Aztec-inspired geometric print mini dress designed by the Parisian label's creative director, Olivier Rousteing. "Long sleeves, structured shoulders, a thigh-grazing hem, and a sultry cut-out in the back," the British department store Selfridge's sales listing reads. Well, it was certainly thigh-grazing. Guilfoyle accessorized her leggy London look with white patent heels, and Don Jr. and the red hats were there for it. "You are really beautiful kim," a fan commented on an Instagram pic Guilfoyle posted. "You are so beautiful Kimberly! You and Don Jr. do so much for our country. Thank you! Trump 2024," another wrote. "That's hot kim," a third chimed in.

The couple was snapped leaving Zuma restaurant after dining with Zimbabwean-British heavyweight boxer Derek "War" Chisora. Earlier in the evening, the three attended a Donald Trump fundraiser hosted by teen soap actor and noughties pop star Holly Valance at her über-luxe Chelsea mansion. "It's a Holly party," Nigel Farage, an alt-right rabble-rouser and Trump toady, told The Times. "You can guarantee it's going to be enormous fun."

So, what's the cost of some Farage fun? Well, $100,000 per couple to join the host committee, $50,000 to attend the reception, pose for a MAGA pic, and sit at a roundtable, $10,000 for the reception only, and $15,000 for a photo.

In October 2024, Kimberly Guilfoyle was a leggy lady in white, posing for a picture with Donald Trump Jr., former Acting Director of National Intelligence-turned-MAGA pitbull Ric Grenell, and singer/entrepreneur Bleona. With its super short hemline, Guilfoyle's $565 Retrofête mini showcased her glamorous gams. Meanwhile, the V-cut neckline allowed for maximum chest exposure. She completed the look with patent white stiletto heels and a pearl choker.

"This dress strikes the perfect balance between elegance and style, designed to make a statement at any occasion," the manufacturer's description reads. Guilfoyle's get-up undoubtedly made a statement. However, what kind of statement is questionable. The Instagram fashion police were decidedly divided on the matter.

"Why are Kimberly's boobs always showing?? We don't need to see them! Cover up! We want a modest and classy first family!" an Instagram fashion police officer demanded. "PUT SOME D**N CLOTHES ON KIMBERLY!!!! U NOT CLASSY AT ALL!! YOU LIOOK LIKE SOMTHING OFF THE VEGAS STRIP!! TIME TO DRESS WITH CLASSS & INTEGRITY SRLF RESPECT!!!! NOT IMPRESSED !!!" ranted a second hater. "Love the legs in pantyhose!" gushed a lover. "@kimberlyguilfoyle Making pantyhose great again!" another raved.

The skin-tight thigh-skimmer that Kimberly Guilfoyle wore to the Furry Friends and Fancy Things fashion show at the Trump National Golf Club in November 2024 was a real eye-catcher. It was hot pink, but unfortunately, the plunge-to-the-navel neckline with a skin-colored rubber panel, glitzy diamanté trim, and hemline that barely covered her butt resulted in Guilfoyle looking a hot mess. 

"A memorable day with @kimberlyguilfoyle ! Honored to connect again with someone so genuine, powerful, and inspiring," Palm Beach model Linda Bertino captioned a photo of the two on Instagram. It's no big surprise that Guilfoyle's leggy look caught everyone's attention, setting the cat among the social media style pigeons and pitting trolls against Trumpers. 

"I'm stunned that they haven't any self-awareness about how déclassé they look. It's not sexy. It's cheap and tawdry. This must be how they think of themselves. Zero class, zero style. Jesus Christ. Just walk around naked for f**k's sake," one user wrote. "Sorry losers! @kimguilfoyle looks AMAZING as always! #MAGAWarrior," the ever-contrary Roger Stone insisted. "She really is stunningly hot AF," a follower raved.

Kimberly Guilfoyle seriously flashed the flesh on a Mother's Day date with her son, Ronan Anthony Villency, in 2024. Her leggy look comprised a $690 powder pink Rebecca Vallance crystal-embellished babydoll mini dress and her trusty white patent stilettos. "Happy Mother's Day Ronan, I have loved every moment of being your mom. You always make me so proud. Being a mother is truly the best job on the planet. Thank you. Love you so much," she captioned a carousel of Instagram pics showing them together over the years.

Guilfoyle fans were feeling the love. "Your son sure has grown up. You both look like Prom Dates," one commented. "Love the au naturale photo of you with your son. The best way to be. Beautiful!" another applauded. "Thank god he's god your looks! Stellar young man!" a third raved.

Ronan, who Guilfoyle shares with her second husband, Eric Villency, is his mom's biggest cheerleader. He's regularly spotted by her side at events, cheering her on from the sidelines and taking to the stage with his (maybe) future stepfather and other members of the Trump family. Guilfoyle paid tribute to the teen on his prom night in April 2024. "Seeing Ronan all dressed up and ready for prom brings back a flood of memories — from his first steps to this momentous occasion. It's a testament to his growth, his character, and the incredible young man he's become," she captioned photos of his big night.