Kimberly Guilfoyle's Worst Pre-Trump Outfits, Ranked

In her days as an attorney, journalist, and former first lady of California, Kimberly Guilfoyle kept her look simple and professional: pantsuits and wrap dresses were her go-tos, usually in black, gray, or single bright colors. Then came Guilfoyle's long relationship with Donald Trump Jr., which began with a casual acquaintance in 2007, progressed to a romance 11 years later, and ended with a broken engagement in late 2024. As she entered the Trump circle, her style became considerably less subtle. Guilfoyle's hair extensions grew longer, her hemlines shorter, her necklines deeper, and her dresses tighter. Though no one knows for sure why she and Don Jr. broke up, rumor has it he felt she didn't present the kind of image befitting a first family. An unnamed insider once told People that Bettina Anderson, the first son's new flame, has more of the pedigree and fashion sense that passes muster with President Donald Trump. "Don Jr. has always wanted to look good in his father's eyes," they said.

Not all of Guilfoyle's fashion missteps can be attributed to her connection to the first family, however. The new U.S. ambassador to Greece definitely made some questionable choices at times in her pre-Jr. days. We've gathered some of the most obvious examples and ranked them from merely unfortunate to totally cringe.

During San Francisco Fashion Week 2005, Guilfoyle showed off her modeling technique when she walked the runway as a special guest. (Though she was on the verge of divorce from California Governor Gavin Newsom, she still had enough clout to merit the honor.) The attorney should have rethought her choice of dress. As becoming as this ruffled number is, it closely resembles the traditional costume of flamenco dancers. Originating in Spain, the art form has a rich and important history, and mastering the dance takes years of study. Since Guilfoyle's background is Irish and Puerto Rican, wearing the style as entertainment looks uncomfortably like cultural appropriation.

Another thumbs-down goes to the ensemble Kimberly Guilfoyle sported at the launch of the Douglas Hannant by Robert Piguet fragrance line in February 2011. A party celebrating a designer French perfume would seem to call for a sophisticated look on the part of the user, rather than a mob wife aesthetic. Guilfoyle's green satin dress looked both cheap and uncomfortable; it pulled tightly in all the wrong places even when she stood in place. And is that a hint of a peplum we spy? If so, that also puts the dress among Guilfoyle's most outdated outfits. The fur-collared coat just added more unnecessary shine. This one gets a mais non from us. 

Here, Guilfoyle poses with journalist Dan Abrams at a screening of "The Door in the Floor," a 2004 Jeff Bridges drama about a marriage marred by tragedy. Alas, Guilfoyle's look was marred as well. The haphazard black and silver patterning on her lace dress and jacket was distracting, and the cut was less than flattering. She might have fared better if the dress were solid black — a safe choice she often favored back then — and the waist narrower. Luckily the inside of the movie theater was dark enough to keep Guilfoyle from getting too much attention once the movie began.

When attending a fashion show, one doesn't have to be as stunning as the models strutting the runway, but one shouldn't try to look cringe, either. Kimberly Guilfoyle temporarily forgot that particular guideline when she attended the 2011 Mercedes-Benz Fashion Week in Manhattan. Her wardrobe for most of the week was quite understated and attractive, but one night, she decided to switch it up with this splashy leopard micro-mini. If the odd color combo on the dress weren't enough of a miss, Guilfoyle added to the mix by wearing pumps (high boots would have looked more chic) and sheer tights where opaque was called for.

In her pre-Trump days, Kimberly Guilfoyle showed admirable restraint when it came to accessorizing. Minimal jewelry and a clutch or handbag was her basic statement. So we're not sure what happened here. For a 2006 afterparty, she opted to pair a basic gray dress with a droopy belt, an oversized coat with silver piping, a waist-length necklace, black scarf wrapped high around her neck, short black gloves, and open-toed heels that looked too delicate compared to the rest of the outfit. The result was a mismatch that looked more junky than funky.

The top spot for Kimberly Guilfoyle's early style era goes to this dress she wore to not one, but two NYC events one day in March 2007. First, she and then-husband Eric Villency attended the opening of an Ermenegildo Zegna store in midtown, and then they went off to a formal dance at the American Museum of Natural History. The dress, featuring a bra top, sheer midriff, and lacy skirt, might have worked at an awards show or gala where daring designs are expected. In this case, it was a poor match both for men's designer shoes and dinosaur fossils. It also unfortunately revealed telltale pale lines rivaling Donald Trump's worst fake tan fails. Lesson learned: If you're going to bare that much skin, it pays to check yourself out in the mirror first.