Sydney Sweeney Outfits That Totally Missed The Mark

Sydney Sweeney has risen through the ranks to become one of Hollywood's most fashionable stars. Sweeney's undergone quite the elegant style transformation since she hit the acting scene, has jaws dropping on the red carpet, and has the biggest fashion houses in the world clamoring to dress her. But, even the best dressed stars on the planet get it wrong sometimes. And, just like Taylor Swift, there are a few looks from the "Euphoria" and "Anyone But You" actor that missed the mark.

That may be because Sweeney admitted in January 2024 that she hadn't gotten totally comfortable with the Hollywood scene. "When it comes to a red carpet, I get nervous because everybody is like, 'Here's Sydney Sweeney!' But in reality, Sydney Sweeney is a girl who is usually wearing no makeup, jeans and a T-shirt, and running around barefoot outside," she explained to Vogue. And that's come across a few times in her fashion misses.

When Sydney Sweeney attended Mattel's 5th Annual "Party On The Pier" in October 2014, it looked like she'd dressed for a different event. We appreciate that she attempted cute and casual for the daytime gathering, but the light matte brown ankle boots didn't work with her mixed-pattern mini dress. Though they can be cute for the fall, Sweeney wore them in October in California, so we're guessing her feet were feeling the heat. They were also an awkward length, cutting off her bare leg at the ankle rather than elongating her pins like a ballet flat or court shoe could have done. The dress itself was also a little confused, mixing patterns and colors for a boho style that just didn't feel authentic for the then up-and-coming star.

Sydney Sweeney was fast becoming Hollywood's new It Girl by 2020, but she stepped out for Covergirl's Clean Fresh Launch Party in a look that January that unfortunately didn't compliment her coloring. She wore a beige blouse, blush pink wide-legged pants and pointed toe heels, plus a nude bag. The individual pieces were stylish, and indeed, wide-leg pants would go on to be huge in 2023. However, the color palette did not suit her. Coupled with her fair skin and light hair, the matchy-matchy neutral tones washed her out. We'd have loved to have seen the star in a different color blouse (she could have kept things neutral in white or black) to create more of a contrast with her skin tone.

Sydney Sweeney attempted the no-pants trend outside of summer while attending the Miu Miu Womenswear Fall/Winter 2024-2025 show for Paris Fashion Week in March 2024, but the look just wasn't flattering. She opted for white embellished hot pants over sheer black tights, with peep toe heels, a black-and-white cop top, and long, black blazer. But because the bottoms were so heavily embellished, the shape added bulk around her hips that made the ensemble look frumpy. "I'd think this were cuter if the bottom wasn't kinda puffy (it reminds me of a diaper)... sydney is cute tho!" one person wrote on X of the outfit. 

We understand that Sydney Sweeney wanted to stay cozy and warm for the premiere of "Big Time Adolescence" at Sundance Film Festival in Utah in January 2019 (and we don't blame her!), but her knitwear brought too much bulk. She wore a cream peplum cardigan with black buttons and puffy sleeves, but the added fluff down her arms off-set Sweeney's proportions and overwhelmed her small frame. That was only enforced by the added peplum and long sleeves, which almost covered her hands. If the cardigan was a little shorter and tapered in at her waist rather than her hips, this could have been quite the chic look.

Sydney Sweeney attended CinemaCon in April 2023 in a look that should have worked. Her shiny, strapless pink jumpsuit felt authentic to her typically feminine and sophisticated style — only the tailoring totally let things down. It fit well at the waist, but the pants were so long the trip hazard hem trailed on the floor and covered her trendy pointed-toe heels. That made the wide-leg bottoms sag and drag the one-piece down, which made the top (which seemed a little small to begin with) slip. Sweeney has spoken out about her difficulty dressing her upper half, telling Glamour UK in 2023, "When a brand is letting me reconstruct the top or rebuild it or alter something, that's when it looks better." And this one could have done with a few more alterations to get it right.