The Most Expensive Outfits Kimberly Guilfoyle Has Ever Worn

Kimberly Guilfoyle's fashion style is a mix of "The Real Housewives" and "Shahs of Sunset" with a large pinch of "Dubai Bling" thrown in. It's an aesthetic greatly celebrated in the reality TV world, where the louder, glitzier, and trashier, the better. In the world of politics and global diplomacy, though? Not so much.

Guilfoyle's fashion fails have become the stuff of legend. There's the breast-baring, thigh-flashing, skintight atrocity she wore to address the audience at a Mar-a-Lago fundraiser in March 2024. That undoubtedly tops the seemingly never-ending list of Guilfoyle's scandalous outfits — no mean feat, given the level of competition. Of course, few can forget Guilfoyle's cheap attempt at cowgirl chic that she wore in a failed attempt at lassoing back Donald Trump Jr.

Shockingly, the gaudy and often outdated outfits that Guilfoyle has been caught wearing don't come cheap. In fact, proving that money doesn't necessarily buy you style, many of the ensembles have an eye-watering price tag. Her closet is crammed with Balmain, Prada, Mui Mui, and other designer duds. At the same time, Guilfoyle's shoe collection is even wilder, with around 500 pairs and counting. "Is that more than Imelda Marcos?" she asked US Weekly during a wardrobe tour in November 2017. That'll be a no. The "Iron Butterly" was estimated to have around 3,000 during her peak power phase. Still, it's always good to have something to aspire to. With that in mind, credit cards are at the ready! We're looking at the most expensive outfits Guilfoyle has ever worn.

Kimberly Guilfoyle was dressed to kill in all her flesh-flashing finery on a night out with Donald Trump Jr. in June 2024. She put her best Jimmy Choo-clad foot forward, strutting her stuff in a black and white knitted Balmain Aztec-inspired geometric print mini dress designed by the Parisian label's creative director Olivier Rousteing.

"It's shaped to the Parisian label's blueprint — long sleeves, structured shoulders, a thigh-grazing hem, and a sultry cut-out in the back. Slip yours on with barely-there heels," British department store Selfridges purrs in its online listing. Skimpy and sultry, it was the perfect match for the va-va-voom-loving Guilfoyle, and what it lacked in material inches, it more than made up for in price tag. A Balmain printed bodycon dress will set you back in the region of $2,495. When you factor in the cost of Guilfoyle's Romy 100 Jimmy Choos — $610 a pair — her siren style clocks in at a cool $3,105.

Guilfoyle definitely isn't one to scrimp on her shoes. When it comes to footwear, she makes it rain, dropping C-notes like a rapper at The King of Diamonds, although even T-Pain might wince at splashing out $1,150 for a pair of sandals. Not K-Guil, though. "There's a whole shelf of Valentino's Rockstuds, which I favor and have them in patent leather in all shades — they have a T-strap and are pretty amazing," she told Footwear News of her shoe collection in December 2016.

After landing stateside following her brief trip to London, Kimberly Guilfoyle upped the expensive outfit ante yet further. She splashed out even more clothing cash on the daytime ensemble she wore to meet with El Salvador's controversial President Nayib Bukele in June 2024. "President @nayibbukele made history by becoming the first two-term President in El Salvador's history," she captioned a carousel of photos posted on Instagram showing her and Donald Trump Jr. hobnobbing with Bukele. "His bold vision for the country will drastically improve the lives of his citizens."

Human rights groups would beg to differ. "Salvadoran authorities have committed massive human rights violations, including thousands of arbitrary detentions and violations of due process, as well as torture and ill-treatment, and at least 18 people have died in state custody," Amnesty International noted in June 2022.

Still, who cares about human rights when there are designer duds to buy? Nobody can doubt Guilfoyle's commitment to the latter, as evidenced by her $1,050 little white Rebecca Vallance embellished mini dress, $4,100 Prada Galleria patent Saffiano mini bag, and $610 Romy 100 Jimmy Choo pumps. Guilfoyle's commitment level was truly impressive at an overall cost of $5,760.

Kimberly Guilfoyle was bringing the Studio 54 shimmering mirror ball back in April 2024. "In each other's corner, taking on life together head-on with determination and dedication," she captioned an awkward Instagram pic of her and Donald Trump Jr., showing off his swagger with a puffed-out chest and cheesy grin. Meanwhile, Guilfoyle stood to attention, stiffly by her fiancé's side, arms straight down, fingertips skimming the hem of her dress. It's possible she was checking to ensure the dress wasn't inappropriately short — an uncharacteristically modest move for Guilfoyle, but you never know. "I go by Susan's mother's rule on how short is too short: Put your arms down at your sides — if your hemline falls below your fingertips, it's safe to wear," Glamour wrote in November 2009.

Rule or no rule, there was nothing uncharacteristic about the cost of Guilfoyle's expensive ensemble. Her $1,998 Retrofete Kaleido embellished strapless minidress and $1,450 Aquazzura Tequila sandals made for an overall outfit investment expenditure of $3,448.

Guilfoyle was dolled up to the nines to celebrate Alina Habba's birthday. She posted a photo of herself in all her mirror-ball glory, posing in front of a swimming pool, sandwiched between Lara Trump and the birthday girl who was giving Guilfoyle a run for her sparkly money in a skintight, bronze, and glittering gold strapless jumpsuit.

Kimberly Guilfoyle takes St. Patrick's Day celebrations very seriously. How seriously? Well, how about $4,315 seriously? That was the eye-watering cost of the outfit she wore to indulge in Guinness, corned beef, and cabbage in March 2024. It comprised a $675 Simkhai Kat embellished mini dress, $1,290 metallic leather Prada platform sandals, and a $2,350 re-edition 2000 crystal-embellished Prada mini bag.

"Celebrating my Irish/Puerto Rican heritage on this Saint Patrick's Day 2024, American style! Wearing green, spreading joy and honoring tradition," she captioned a photo on Instagram of her in front of a giant inflatable leprechaun and four-leaf clover. Well, she was correct about celebrating in American style. Most self-respecting Irelanders wouldn't be caught dead anywhere near an inflatable leprechaun. "For generations, some Irish have been annoyed by leprechauns and the ethnic stereotypes they perpetuate, and for most Americans, leprechauns only appear around St. Patrick's Day," Live Science notes.

Meanwhile, although the actual extent of Kimberly's Irish roots is unknown, her last name is steeped in Emerald Island history. "The name Guilfoyle in Ireland is derived from the native Gaelic Mac Giolla Phoil Sept that literally translates as 'a devotee of Saint Paul'. The Sept was based in County Offaly and it is here that the majority of descendants can still be found," Irish Surnames explains. "A Sept is an ancient form of a Clan and is a group of people whose ancestors all bore the same surname and inhabited the same locality."

Kimberly Guilfoyle is clearly a firm believer in the age-old adage "charity begins at home." This is evidenced by the ludicrously pricey get-up she wore for a charity fundraising dinner hosted by Furry Friends Jupiter at her and Donald Trump Jr.'s palatial Florida mansion in February 2024. Guilfoyle was clad in a pair of $2,033 Mui Mui Nappa silver leather platform sandals and a $5,950 black sequin Balmain mini dress. At a combined cost of $7,983, it tops our list of the most expensive outfits Guilfoyle has ever worn.

"Together, we indulged in a delightful evening filled with gourmet courses prepared by a renowned chef, @chefaustinsimmons, all in support of our furry companions at Jupiter," she captioned a carousel of pics and vids from the big night posted on Instagram. "Thanks to the generosity of our attendees, we raised crucial funds to support the welfare and care of our beloved furry friends. Your contributions make a world of difference in their lives. Stay tuned for more updates on how your kindness continues to impact the lives of our four-legged friends!"

Apparently, Guilfoyle's love of animals runs deep. This may come as a surprise to many, given her passion for slaughtering beautiful beasts in the wild when hunting, or when they're used to create the materials for her designer clothes and shoes. However, according to Stroll Mag: "[Guilfoyle's] a lifelong supporter of rescue animals. Growing up, her family always adopted rescue pets, and she has carried on the legacy, using her platform to advocate for shelter animals."