Kimberly Guilfoyle's Outfits Were Awful Long Before She Started Dating Trump Jr. (Here's The Proof)

There have been numerous critiques of Kimberly Guilfoyle, including but not limited to her rather polarizing wardrobe. While some love the way she dresses, others — including even Donald Trump fans — have turned on Guilfoyle for outfits that were deemed inappropriate, such as a dress with a plunging V-neck covered in mesh. Most of the ensembles that are considered unsuitable by critics tend to show a lot of skin, but other times they just do not fit the vibe of wherever she is going. 

One notable instance occurred when the former Fox News host attended the 2024 presidential inauguration in El Salvador; Guilfoyle went from a white minidress to a Morticia Addams reject — a black dress with furry sleeves. Although it may seem like she only started dressing so drastically after beginning her relationship with Donald Trump Jr., Guilfoyle has always had an interesting fashion sense. Her outfits were awful long before she butchered the Barbiecore trend.

In November 2005, Kimberly Guilfoyle was photographed at the opening of a John Varvatos store in New York City. For the occasion, she opted for an all-black outfit. Her top was babydoll-style, done in black satin, and her knee-length skirt seemed to be made of the same material. The former Fox News host's accessories —a belt, watch, long necklace, and tall boots — were black as well. Although black is a classic color, the nearly identical styles of the top and skirt made the outfit seem one-note and kept it from being memorable. 

In addition, all-black outfits remind people of funerals and mourning, which is likely not what Guilfoyle was aiming for. Plus, monochromatic black looks can age you. Artful pops of color are a great option to mix things up, which Guilfoyle should have considered when getting ready for this event.

How much accessorizing is too much? One of Kimberly Guilfoyle's outfits from her pre-Trump days may just be the blueprint. In February 2006, she attended the glamorous afterparty of a Marc Jacobs fashion show, opting for a gray, knee-length dress with a thick black belt and a matching black overcoat with silver trim for the occasion. That would have been enough, but the outspoken political commentator kept it going with a long, thin silver necklace, a black scarf and gloves, and black high heels adorned with small bows (perhaps foreshadowing Guilfoyle's disastrous love for the coquette trend).

The disparate elements of the ensemble make it feel scattered and too busy. Since the party was in February in New York City, Guilfoyle may not have worn the outerwear (the coat, gloves, and scarf) for the entire event. However, even without those pieces, the colors could be a bit brighter. The slate-colored dress would be more appropriate for the office, not celebrating a new Marc Jacobs collection.

One feature that Kimberly Guilfoyle loved in the past and still adores today is a keyhole cutout in a plunging neckline. While being photographed at the Plaza Hotel for the Douglas Hannant fashion show in September 2009, Guilfoyle wore a white knee-length dress with thin black swirls. The bodice featured a large keyhole cutout, around which large black flowers with fake gems in the center were embroidered. Don Jr.'s fiancé also had a black clutch purse, black shoes, and a clear bracelet as the final, cherry-on-top accessory.

The dress' swirling pattern was dizzying, but the chunky black flowers are the real killer here. It shows that Guilfoyle's taste has not changed all that much. For example, she still wears dresses with sparkly elements around bodice cutouts. The cutouts have gotten larger and more bold, though. For instance, in photos shared to Instagram in May 2024, the former Fox News host's red minidress had silver hearts holding a cutout together, but a bit of skin on her abdomen was still visible.

At a fashion show for Tibi in February 2011, Kimberly Guilfoyle attempted to show her wild side with an animal print dress. The tight-fitting number featured a dark green and tan background and was covered with black and pink leopard print. Underneath the minidress, she donned black tights, topping off the look with dangling earrings, black shoes, and bright red nail polish. The main offense with this are the colors of the animal print itself. 

The bright pink isn't cohesive with the green, which is a more muted shade. Additionally, Guilfoyle should have painted her nails the same pink shade as the dress — or worn something entirely different. The staunch Trump supporter might have abandoned animal prints for glitz and glitter. She wore a dress with mirrored gold beads for a birthday party in March 2024, and Guilfoyle looked totally opposite to Donald Trump Jr. at that event.

Kimberly Guilfoyle's penchant for minidresses can be traced all the way back to her previous, pre-Trump days. In October 2010, she was a guest at the Couture Lingerie Runway Show and Gala held by Freedom Bay St. Lucia. The proceeds went towards the Seven Bar Foundation's microfinance programs combating poverty for women. For the glitzy event, Guilfoyle chose a mauve dress with a halter top bodice, small buttons, and a layered skirt with multiple ruffles paired with silver heels and a purple clutch purse.

Although the skirt of her dress reached Guilfoyle's knees, the sheerness of the final ruffle made it appear more like one of her favorite minidress styles. Further, photos from the event on the Manhattan Society SmugMug showed that her dress didn't really fit the gowns worn by other attendees who focused on cleaner lines and richer colors, making Guilfoyle's outfit look far too casual in comparison. Will she break out any of her old styles for future events, or is the former Fox News host strictly sticking to coquette dresses now?