Hallmark Star Kimberly Williams-Paisley Has Worn Some Outfits That Just Didn't Work

Kimberly Williams-Paisley has had some fun with fashion over the years. The "Father of the Bride" actor turned Hallmark star has pushed style boundaries multiple times, including when she wore a geometric, black-and-white ball gown with invisible straps at the 2009 Unicef Gala. That risk paid off to become one of her most elegant looks to date — but not every experimental look has worked.

Williams-Paisley has even publicly aknowleged that at least one of her ensembles could have done with more forethought. In 2019, she posted a photo to Facebook alongside the caption, "Just left for the DAY in an outfit I just realized I cannot get off to pee without assistance." She added a selection of hilarious captions, including "#sos," "#assistanceneeded," and "#whatwasithinking." Though her full outfit wasn't visible, the star appeared to be wearing a light blue jumpsuit or romper with white and black lace detailing.

But her other fashion mishaps weren't down to impracticality. Just as her husband Brad Paisley's former CMA co-host Carrie Underwood has had a few outfits that just didn't work, Williams-Paisley's worn a handful of 'fits that needed a second look, including ensembles that swamped her frame and several odd boot choices.

Back in 2002, Kimberly Williams-Paisley (then known as Kimberly Williams ahead of her marriage to Brad Paisley) left us confused when she paired tall, suede boots with a light gray, midi skirt to attend a ECO and Greenpeace event. She wore the pieces with a leather-look, neutral jacket and floral top with sheer material over the chest. But the footwear didn't fit with her outfit's spring theme or the location (she was in Malibu in May) and made the whole look feel mismatched and confused. We'd have recommended swapping the boots for heeled sandals, or saving the look for fall and changing the skirt for a pair of jeans for a trendier aesthetic.

Kimberly Williams-Paisley was only 27 when she walked the red carpet for the 1999 premiere of "Simpatico," but her all-black ensemble was an outdated fashion trend that made her look older. Though she attempted to make is more youthful via her plunging crop top, the long sleeves, shin-length skirt, and black boots were too matchy-matchy in a drab and boring way. The 'fit would have felt more fun if she'd injected a pop of color with her accessories or worn strappy heels.

Thankfully, the star learned her lesson. When asked by Southern Living to describe her style 25 years later, she responded, "Comfortable and colorful. It's become a little more whimsical since I had my two boys."

Kimberly Williams-Paisley walked the red carpet for the "Beauty & The Beast Sing-Along" event in 2010, but it looked like she'd stumbled across it. She looked more appropriately dressed for a day at the mall in her black, gray, and maroon, layered tank tops paired with skinny, black jeans, and sparkly, black ballet flats (which had a revival in 2023) with an oversized bag over her shoulder. Though trendy for the time, the ensemble was far too casual and made her look out of place next to the likes of Phoebe Price and Paige O'Hara, who dressed with a premiere in mind in cocktail dresses and heels.

At the 2006/2007 ABC Upfronts, Kimberly Williams-Paisley wore calf-high, brown, leather-look pointed toe boots with knee-length brown shorts, and a strappy, orange and brown, patterened top. Showing just her knees felt odd though, as tall boots are more flattering with short shorts. We also weren't sold on her top, as the turquoise ribbon that hung from her chest was off center and a totally different color to the rest of the garment.

Even she agreed this look didn't work, as she appeared to refer it as her worst in a Southern Living interview. "The shorts were baggy, and so were the boots. It was a really bad combination," she said.

While we give Kimberly Williams-Paisley props for taking a risk at the 2022 Gracie Awards Gala, her pink dress missed the mark. Her black and white, big and small polka dot gown featured several rows of vertical frills down her torso and a long, black bow around her waist. But, unfortunately, the bold print and excessive material swamped her small frame. The oversized texture added bulk on her top half that wasn't flattering and, coupled with the double layer of patterns, made the dress feel more like an optical illusion than a chic gown. It also needed better tailoring, as the hem dragged along the floor, completely hiding her shoes.