Shailene Woodley's Biggest Fashion Fails Of All Time, Ranked From Bad To Worse

Being a public figure comes with its challenges. Not least of all is the way you look, as people love to pick apart celebrities' bodies, beauty, and fashion choices. Shailene Woodley has certainly been under the spotlight several times herself, despite her stunning transformation over the years.

Woodley's fashion went viral for all the wrong reasons at the 78^th Primetime Emmy Awards on September 14, 2026, when she made many critics' worst-dressed lists. The "Big Little Lies" actor wore a Balenciaga haute couture outfit that seemed totally mismatched, with silver sequin pants, an extremely low-cut blue tank top, burgundy leather gloves that reached over her elbows, and a $98,000 necklace by HOWL. It was odd and disjointed, and it sparked tons of hilarious roasts on social media.

"Me when I'm getting ready to clean the toilet," one person wrote on X. Another lamented, "There's a new generation of girls who have never been bullied by Joan Rivers and that's unfortunate."(Known for her hilarious red-carpet fashion critiques, the late Joan Rivers certainly would have had a lot to say about Woodley's outfit!) Everyone has off days, but "The Secret Life of the American Teenager" star has experienced a lot of these over the years — with many fashion flops almost as bad as her Emmy's look. In fact, that's not even the worst outfit Woodley has rocked on the red carpet (yes, seriously!), making her one of the worst-dressed celebrities of 2026. See her biggest fashion fails, ranked from bad to worse, below.

Does Charles Ingalls from "Little House on the Prairie" know that Shailene Woodley stole his look? Her outfit at the Christian Dior Womenswear Spring/Summer 2023 fashion show in September 2022 certainly looked like it came from the prairie, with her black, wide-brimmed hat and black button-down shirt tucked into khaki pants and held up with black suspenders. She looked ready to milk cows and teach Laura some valuable life lessons.

If you said Shailene Woodley took a glue gun to her t-shirt the night before the Golden Globes Gala Dinner at the Red Sea International Film Festival in December 2025, we would totally believe you. Her cropped black t-shirt certainly appeared DIY with what looked like black plastic tassels glued on front. It was very odd, like what you might see if you were creating your own Halloween costume. She paired it with a black pencil skirt and over-the-elbow black leather gloves.

What in the early 2000s was Shailene Woodley wearing at the Christian Dior Womenswear Spring/Summer 2019 show in September 2018? Her newsboy cap looked like something straight out of the Y2K era, and even though fashion houses tried to bring it back in 2018. Woodley's didn't quite achieve the high-fashion statement though, as she paired it with a black t-shirt and maxi skirt, with a thick black belt around her waist like it was still 2007.

Shailene Woodley was already channeling autumn at the Met Gala in May 2014. She wore a Rodarte dress that couldn't decide on a theme. It had orange-and-tan flowers sewn onto the sheer arms and bottom part of the dress. Underneath was a brown sequin mini skirt. The bodice was gray with orange butterflies and sequins in an upside-down V-shape, with a silver bust in a straight neckline that showed off her shoulders. It was awkwardly put together and not cohesive at all.

Shailene Woodley's dress at the "Endings, Beginnings" premiere in September 2019 was all over the place. It's as if she tried to hop on board several different trends at once, meaning none of them truly worked very well. Her short dress featured bold, geometric patterns of white, blue, and purple, with a matching purple mini cape that fastened to her bodice. On top of that, the dress had pockets — which is normally a good thing, but added to the awkwardness when Woodley emphasized them by posing with her hands inside them. Black combat boots added to the overall disjointed effect.

Mixing patterns is a skill, and one that Shailene Woodley unfortunately doesn't seem to have. Case in point: her outfit at the Louis Vuitton Maison store launch in October 2019. She wore a white blouse with a bold leopard print pattern along most of the top half of her blouse, save for one shoulder. This was strangely paired with a yellow and black checkered skirt and black sneakers, which looked so odd together that it seems like she accidentally grabbed the wrong skirt when getting dressed.

Have you ever thought, "Hm, I wonder if antique lampshades would make a great dress?" You probably haven't, and Shailene Woodley's outfit at the 2^nd annual InStyle Awards in October 2016 proves why that was the right call. Her halter top featured brown and tan stripes with a wide khaki strap and a gold tassel fringe along her hips, which looked just like a lampshade. Her skirt continued the old-fashioned vibe, with a muted flower print that could have been curtains in another life.

There's no other way to say it: Shailene Woodley's outfit at the Emmys in September 2026 was downright weird. The light blue tank top that nearly dipped to her navel and shimmery pants were odd enough, but the burgundy gloves and colorful statement necklace sealed the outfit's spot on Woodley's worst-dressed list. Even her hair looked strange here, as it was parted in the middle and pulled back in a low ponytail at the nape of her neck.

A mix between a pool floatie and Hilary Duff's igloo dress from "The Lizzie McGuire Movie," Shailene Woodley's outfit at The Fashion Awards in December 2019 stole the show for her worst fashion fail ever. The huge inflatable dress was puffy and awkward, as it hung to the ground. The royal blue dress was paired with a striped blue-and-white poncho (also inflatable, by the way) and a hood that was pulled over her head. It seemed to swallow her up and was so strange we couldn't believe it made it past the drawing board.