“She’s a small-town girl from Washington. Both of us were tomboys back then, without a clue about fashion, but now she’s getting to know all the designers,” shared Molly Dickson, stylist to Sydney Sweeney, on her remarkable fashion transformation during a conversation with Vogue. Dickson continued, “She’s gaining an understanding of the significance of tailoring and what flatters her physique.” While Sweeney’s style journey has been impressive, she hasn’t always made perfect choices.

At the red-carpet premiere of Netflix’s film “Bright” in 2017, a then 20-year-old Sweeney arrived in a delicate Self-Portrait dress adorned with floral prints, mesh panels, and intricate netting along the shoulders. The ensemble was so elaborate that her impressive legs went unnoticed. She kept accessories minimal, opting only for earrings and teamed the playful dress with matching velvet boots from Los Angeles brand Avec Les Fillers. Despite this, the combination suggested a sense of fashion uncertainty rather than refined taste.

Sydney Sweeney is often a showstopper on the red carpet, but this particular look leaned towards the mature side. In 2022, she graced the Hollywood Critics Association TV Awards in a vintage Mugler piece from the fashion house’s 1981 Haute Couture collection. Her accessories, reminiscent of a Real Housewife’s style, included a diamond-encrusted necklace, a matching bracelet, a stack of rings, and gold pointed-toe heels from Jimmy Choo. Unfortunately, this ensemble was not a standout. Better luck next time, Syd!

Who let Sydney Sweeney leave the house dressed like this? At The ELLE Super Bowl in October 2017, the “Anyone But You” star stepped out in a no-frills blue pencil dress with thin straps and a sweetheart neckline that screamed bo-ring, even with her legs on display and a pair of Steve Madden’s Glory platform heels. The braided pigtails were a pretty odd choice, too. Sweeney probably wishes she could erase this fashion blunder from the photo archives, but instead it forever remains as a moment when her styling powers weren’t up to scratch.

Sydney Sweeney always knows how to turn heads on the red carpet, but this look struck us as a bit matronly. In 2022, she attended the Hollywood Critics Association TV Awards wearing an archival Mugler frock from the fashion label’s 1981 Haute Couture collection. Even her accessories looked like something a Real Housewife would wear; she finished it off with a diamond-encrusted necklace, matching bracelet and stack of rings, and gold pointed-toe heels from Jimmy Choo. Not exactly a winner in our eyes. Sorry, Syd!

Honestly, we don’t know where to start with this outfit. Should we begin with that hideous leather skirt that not even her killer legs can save? Or her leg warmer plus kitten heels situation? As a longtime muse for Miu Miu, Sydney Sweeney should have offered something more fashion-forward and less head-scratching than this… monstrosity. She wore this lewk at Miu Miu’s Fall/Winter 2025 runway show in Paris, sitting front row with the likes of Gigi Hadid and A$AP Rocky. The shades were a nice touch, though. 

What is with Sydney Sweeney and ugly skirts? The actor channeled Cher Horowitz in this mint-green skirt suit from Thom Browne while doing press for her movie “Reality” in 2023. “She either needs a better stylist or better style lol whomever is making these decisions is struggling,” one Reddit user said of Sweeney, to which another fan agreed: “Yeah a lot of people are commenting on the fit of the clothing, but I feel like a lot of the colors are off … Some of these other colors are doing nothing for her.” We’re with them on this. 

At the 2024 “Immaculate” world premiere during South by Southwest in Texas, Sydney Sweeney showed up as a runaway bride in a lacy Richard Quinn dress with an off-shoulder neckline and a daring thigh-high slit. She paired it with lace stockings and classic white heels, and sported a chic bob. Unfortunately, her legs weren’t looking as immaculate as Sweeney and her stylist Molly Dickson had aimed for; as one Reddit user put it, “Hate the lace stockings.” Another wrote, “This is wayyyy too bridal/costumey for me.” 

The proportions are just not proportioning. Here, Sydney Sweeney was captured leaving a boxing gym in New York City while clad in a vintage gray cropped jacket-and-shorts suit from Alaïa’s 1988 Spring/Summer collection. As chic and stylish as her ensemble is, the cropped jacket and high-waisted shorts threw off her proportions, making the “Euphoria” star look shorter. She completed the look with sheer tights that showed off her legs, black sunglasses, a mini handbag, and lace-up heels from Jimmy Choo, but a longer jacket would have created a more flattering silhouette overall.