The Strangest Things Blake Lively Was Caught Wearing

It must have been fate that Blake Lively's first big acting role was in a movie that featured a pair of jeans. The "The Sisterhood of the Traveling Pants" star has made a name for herself not only as an actor, but also as somewhat of a fashion icon thanks to her red carpet appearances. Whether she's with husband Ryan Reynolds playing the Hollywood power couple facing divorce rumors, or flying solo as a party of one, she's always dressed to impress. But sometimes, we are not impressed.

"My style is just all over the place," she once told People, and we believe it. How else could the "A Simple Favor" and "Another Simple Favor" star manage to look completely glam in a designer gown one day, and like it's high-end laundry day the next? 

The fact that she's usually her own stylist could partially explain it, too. "I love design and I love fashion and it's a way to be creative," she shared with WWD about why she prefers to pick out her own clothes. Based on some of the outfits we've caught her wearing, though, we have to wonder if she might need a little help with the wardrobe editing.

When you can't decide if you want to buy cotton candy or a dress, you compromise. In July 2024, Blake Lively hit New York's Upper West Side wearing a sweetly patterned pastel dress — up top. The skirt, however, took a strange turn with layers of frothy feathers swirling about her legs like spun sugar at a carnival. The shoes matched the bottom half of the dress with their rainbow glitter finish, while the long chain belt was matched to the top half. We can only imagine how many minutes she spent picking feathers out of the belt later that night.

Blake Lively shared with People that the fashion vibes from her film's characters often find their way into her own closet. We're trying really hard, but we cannot recall one time when she played a cowgirl or Mr. Rogers. And yet, during a New York City night on the town in August 2024, she dressed in an odd combination of chaps and a cardigan. The grandma sweater might have been due to a fear of air-conditioning chills, but we couldn't find a reason for the jeans with the chaps sewn in. At least her mane wasn't one of her most disastrous hairstyles. 

Some things are just hard to explain, and we're topping that list with Blake Lively's outfit in October 2024. Although her accessory was totally on point (we're looking at you, Ryan Reynolds), everything else about what the "Gossip Girl" alum wore has us shaking our heads. The sheer dress was slit up to the hip on each side, leaving front and back panels to slip and slither between her legs — which were covered by some sort of sheer tights with seams and a built-in run. Though they matched the dress color, the boots' chunky profile did not match the delicate fabric. 

Is it rubber? Vinyl? Latex? And why? At the SXSW festival in March 2025, Blake Lively arrived on the scene wearing a demure mauve dress with short sleeves, buttons, and a collar, although the fabric making it up was unclear. But the joke was on us, because shortly after hitting the red carpet, she peeled off her outer layer to reveal a shiny strapless gown underneath. We're not entirely sure why Lively was wearing the overlay to begin with; it wasn't heavy enough to serve as a warming jacket, and it wasn't raining, so the material seemed odd. We are pretty sure, however, that she may have squeaked when she walked.

On another New York outing in August 2024, Blake Lively may have been trying to help everyone stay awake in the city that never sleeps — her three-piece mixed-patterns outfit couldn't get much louder. A sleeveless blouse filled with big and small dots floated all the way down to her ankles, swirling around a pair of baggy pants patterned with giant flowers. And to cap the whole thing off? A long jacket made of yards of matching floral material, which she wore draped from her elbows. You won't find this one on Lively's most gorgeous looks list.