Spooky season is the time when celebs like Olivia Rodrigo and Jenna Ortega come alive. Their signature edgy style is heightened during the month of October, putting further emphasis on the dark and punky undercurrents of their wardrobes. It's not, however, the time you'd expect girly-girl stars—like Sabrina Carpenter, for example—to shine.
The "Please Please Please" singer is known for her hyper-feminine, Polly Pocket style, which leans heavily on babydoll designs like lace jumpsuits and custom, crystal-coated lingerie. But she put all that aside for her latest look, delving more into "dark academia" territory fit for Taylor Swift's Tortured Poets Department era fashion (read: a crop top and plaid skirt).
On Oct. 7, Carpenter popped out in NYC wearing a look that felt unequivocally fall. She was bathed in plaid (the unofficial print of the season), wearing a midi-length skirt with accordion pleats and a moody gray-and-mustard color story. Leaning further into the spooky librarian look, she merchandised the statement piece with a mock-neck crop top in inky black.
Sabrina Carpenter abandoned her all-pastel wardrobe for a moody fall look.
A major departure from her usual all-pastel color palette, Carpenter accessorized with even more dark details. She wore a glossy oxblood shoulder bag and a pair of archival Gucci mules. The brand recently dropped a modernized iteration of the style, however, you can easily find Carpenter's exact style for a fraction of the prince online.
Beyond Carpenter, even more femme-leaning celebs are trading up their mini dresses and corset tops for darker styles. Taylor Swift, too, has seemingly been bitten by the punky bug, as the pop star went full goth on the VMAs red carpet last month. Like Carpenter, she went for a yellow plaid skirt with all-black accessories—and her favorite Nars lipstick. (Swift's outfit came from Dior's Cruise 2025 collection.) Swift also wore her fair share of plaid mini skirts while out and about between stops on the Eras Tour.
Taylor Swift walked the VMAs red carpet wearing a yellow plaid high-low skirt and corset.
Looks like leaves aren't the only ones changing color this season...
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Olivia Rodrigo Wears the Bodysuit Version of Kim Kardashian's $1,808 Bondage Leather Dress to Headline LollapaloozaThis is the edgiest she's ever looked.
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Katie Holmes's $790 Glove Flats Are the Fashion Girl Version of a Plain Black PairShop her exact pair here.
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Bella Hadid Abandons Her Rodeo Girlfriend Aesthetic for a Khaki Trench Coat and $3,550 Saint Laurent BagThis is the least "Bella" she's ever looked.
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Jennifer Lopez Accentuates Her Skintight Broadway Premiere Look With a $2,950 Bag and Faux Fur CoatShe's so back.
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Rihanna Styles Two of Chanel's Rarest Archival Bags With Puma Sneakers and a Baseball JerseyThese twin totes are extremely rare.
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Dua Lipa Borrows Bella Hadid's Country Aesthetic in Daisy Dukes, Cowboy Boots, and a $6,000 Chanel BagHer take comes with a $6,000 Chanel bag.
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Emily Ratajkowski's $4,400 Burgundy Belted Prada Bag Combines Two Inescapable 2025 TrendsBut her take doesn't feel overdone.
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Selena Gomez Contrasts Her Benny Blanco Date-Night Essentials With a $9,300 Schiaparelli Nose Piercing BagShe and fiancé Benny Blanco also matched boots.
