Reese Witherspoon Outfits That Totally Missed The Mark

Reese Witherspoon has had a stunning hair transformation over the years, but her fashion style has remained pretty much the same throughout her career. Known for her fresh-faced, girl-next-door look, Witherspoon's aesthetic has always been feminine and classic, with a touch of flirtatious appeal. "I've always been Southern ... so I've always been attracted to that J.Crew preppy look with more color and sense of humor. Even when there are boho vibes going on in California. I don't feel comfortable in cutoff jean shorts. I think they're really cute; they're just not my personal style," she told People in 2015.

With Witherspoon sporting countless glam looks on the red carpet, many would love to raid her closet. Unfortunately, not all of her outfits have proven to be winners, and she's had some fashion missteps that just did not flatter her petite frame. As a busy mogul who is running a business empire while providing the best non-fiction picks from Reese Witherspoon's Book Club, fans can't expect the "Legally Blonde" star to be best-dressed all the time, but some of her outfits missed the mark so much that they had us wishing we could bend and snap them away.

While Reese Witherspoon had a prolific acting career since childhood, "Cruel Intentions" was a film that showed her in a more grown-up role. Her character often dressed in preppy outfits, but Witherspoon made the curious choice to go for a more boho look during the 1999 premiere. The "Pleasantville" star wore a long, cream-colored tunic with a gold ribbon tied around her waist, paired with a purple ankle-length skirt that needed a good ironing. With her blonde hair curled and styled in a messy half-updo, Witherspoon looked like she was on her way to a Renaissance Fair. At 22-years-old, she likely didn't have her signature style figured out, but this is one look that needs to stay in the days of yore.

In 2018, Reese Witherspoon took a break from rom-coms and dramas to star in the fantasy movie, "A Wrinkle in Time" as a fairy named Mrs. Whatsit. She could have used the premiere to take method dressing to the next level while promoting her movie and worn an ethereal gown, but Witherspoon sadly opted for a light blue sheath that looked more appropriate for a PTA meeting. The metallic stud detailing on the skirt added a bit of flair, but otherwise, the dress was a dud. From the high scoop neck to the puffed sleeves, it looked like Witherspoon was channeling her inner grandmother and not the free-spirited sprite from the book-turned-film. This 'fit would have been perfect for Witherspoon's character, Madeline Mackenzie, of "Big Little Lies" but it was definitely a far cry from Mrs. Whatsit.

As a celeb who seems to love the business casual aesthetic, it wasn't surprising that Reese Witherspoon wore a navy shirtdress while promoting her rom-com, "Your Place or Mine," in 2023. During a photocall, she chose a slightly structured button-up frock with big cargo-like pockets on the skirt and an odd panel on the bottom that was not necessary. It looked as though there was an extra piece of fabric left on as an afterthought, and it made a simple silhouette look messy. Although a simple snip would have made this outfit better, it was still a boring choice, especially with her plain matching pumps. We think a jolt of color, like a pair of red sandals, would have given this look some life while promoting her feel-good film.

2018 was not Reese Witherspoon's year for fashion, as she attended the LA Dance Project Gala in October of that year looking like she came out of a time warp. While little black dresses can almost never go wrong, the "Walk the Line" star's choice that evening was just that. With the puffy pleather sleeves and large ruby rhinestones on the bodice, the knee-length dress looked like it came right out of the '80s. What's more, the skirt had a leopard print that just added to the overall busy look. Witherspoon's clothing tastes are usually more chic, but this 'fit should have been tossed in the "next" pile.

Fans of Reese Witherspoon know that she's a Christmas gal, which was evident by the tinsel-decorated LBD she wore to the 2017 Gotham Awards. The event took place in November that year, and it seems Witherspoon was already getting into the holiday spirit by dressing herself up as a Christmas tree. Her black sheath featured a row of shiny gold material starting from her shoulder and trailing down to the hem. The tinsel accent, along with its placement, was a very strange choice, and it looked as if the designer just haphazardly glued it on. Perhaps this dress was a leftover from her 2008 film "Four Christmases," but at least Witherspoon shone brightly on the red carpet.