Teeny-Tiny Kimberly Guilfoyle Outfits That Should've Stayed In Her Closet

Donald Trump's second presidency brought a lot of changes for Kimberly Guilfoyle. She became single again in December 2024 after she and Donald Trump Jr. ended their four-year engagement. Unlike her ex, who immediately moved on with socialite Bettina Anderson, Guilfoyle opted to take her time before jumping into a new relationship, but hinted in late 2025 that she was open to getting "a new husband," according to The New York Times. Earlier in the year, she also became an empty-nester after her only child, Ronan Anthony Villency, graduated high school and began his freshman year at the University of Miami. And like her son, Guilfoyle began a new chapter in her life in the fall of 2025 when she moved to Greece and officially kicked off her role as the U.S. ambassador to the European nation that November. Despite getting a fresh start in Athens, however, some things never change for Guilfoyle, and one of them is her obsession with tight outfits that bare plenty of skin.

Guilfoyle's love affair with mini dresses and skirts can be traced all the way back to her days as a model in the 1990s. While she often went for more modest business casual looks during her stint as a prosecutor and as Mrs. Gavin Newsom in the early 2000s, the hemlines of her ensembles grew progressively shorter throughout Kimberly Guilfoyle's transformation into a Fox News host and Trump-verse fixture. However, while we're all for having signature style, Guilfoyle's fashion preferences haven't evolved much beyond 2010s club-wear and high school party looks, so she misses the mark more often than she scores when she debuts another ultra-leggy outfit. From the tacky to the inappropriate, let's take a look at Guilfoyle's teeny-tiny outfits that she probably should have thought twice about before wearing. 

Kimberly Guilfoyle took a break from ambassador duties in January 2026 to catch the Elie Saab show at Paris Fashion Week. For the event, she recycled a sequined white frock with a sheer corset-style bodice and feather hem — a look she previously wore in 2024 to promote a children's book, making it one of Guilfoyle's most inappropriate outfits yet. This time, she styled it with a short fur coat, but unfortunately, it didn't make the dress look any less tacky or the feather hem look any less like a botched DIY project.

When you think of outfits ambassadors typically wear, miniskirts probably wouldn't make the list, right? However, from the get-go, Kimberly Guilfoyle showed she wasn't planning to follow her predecessors' lead when she donned a short tweed skirt and a matching jacket in May 2025 to receive her certificate for finishing her ambassador training. This continued after she started her job later that November. For instance, she donned another skirt that stopped well above her knees when she attended a meeting with top officials of Greece's Health Ministry. 

If we saw this photo without context, we'd probably assume Kimberly Guilfoyle was getting ready to enjoy a night out with the girls. But she apparently thought an LBD with a plunging neckline and risqué slit was perfect for a campaign event, as she wore the look when she hosted a fundraiser for Donald Trump-endorsed Arizona Rep. Abraham Hamadeh in March 2024. The towering gold heels and mesh panels across the V-neckline and slit only added to the Las Vegas magician's assistant vibe of the outfit.

By January 2026, Kimberly Guilfoyle was already knee-deep in her duties as U.S. ambassador to Greece, but it seemed her wardrobe still hadn't been updated with more professional attire. According to an Instagram update, she met with U.S. Defense official David Baker in Athens to discuss the "strong defense ties" between the two countries, but her ultra-short black-and-white dress seemed a bit too casual for such a meeting. Some of her followers noticed this ongoing trend, with one concerned user suggesting that her "skirt length must change."

Kimberly Guilfoyle very much gave big "mom trying to look hip" energy in a 2025 Mother's Day photo, thanks to her pink tweed dress and white platform heels. It didn't help that her eye makeup looked too heavy for the outfit and that her hair extensions looked far too obvious. Perhaps it wouldn't have been so bad had the dress not come in that bright pink shade, which reminded us that she's too late for the "Barbie" trend and made it an outdated outfit Guilfoyle never should have worn.

Kimberly Guilfoyle might have mixed up her main event and afterparty looks in November 2024, as she graced Oscar Lopez's runway show in Jupiter, Florida looking ready for a night of revelry instead of what appeared to be an afternoon of tea and fashion. Her hot pink bodycon dress came with an ultra-plunging neckline that extended to her waist and a tiny bit of illusion mesh fabric, which was probably the only thing preventing Guilfoyle from committing another fashion mishap that would have heads turning.

Kimberly Guilfoyle welcomed 2024 by sharing a post on Facebook wishing her family, friends, and fans "unwavering courage, incredible moments, and the realization of [their] wildest dreams" in the coming year. However, judging by the outfit she wore in the accompanying photo, she seemed to be looking back at the past instead of looking forward to the future. She rocked a long-sleeve tan sweater mini dress and thigh-high white boots — a combo that had us checking our calendars to see if we indeed rang in 2024 and not 2014.

Kimberly Guilfoyle's Instagram post for Mother's Day in May 2025 featured no less than four different short dress looks, but this blue one took the cake for tackiness. The frock was designed with massive puffy sleeves, large rhinestone ribbons, and cutouts from the neck to the waist. Without the latter, the dress looked like something a 6-year-old would pick out for herself for a birthday party. But with the cutouts plus the ribbon details, it wasn't just childish; it was also trashy. 

Kimberly Guilfoyle channeled Kim Kardashian when she and her then-fiancé Donald Trump Jr. were spotted grabbing dinner in London in June 2024. However, it wasn't Kim K. of 2024 but rather Kim K. of 2018. The former prosecutor donned a figure-hugging turtleneck mini dress with an art deco print and 1980s shoulder pads, pairing it with white pumps and statement earrings. While Kardashian has long since branched out to other styles, Guilfoyle seems to be stuck in the past based on her love for this dated silhouette.

Kimberly Guilfoyle didn't steal the spotlight at Donald Trump's April 2024 Florida fundraiser — she was the spotlight. Based on this Instagram photo, her blinding disco ball cosplay of a dress stuck out like a sore thumb at the gathering held to raise money for her boss' presidential campaign. Aside from probably temporarily blinding any guest who looked at her outfit a little too long, the frock appeared to have been created by gluing strips of crumpled up metallic wrapping paper on fabric, leaving it looking cheap and poorly made.