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Taylor Swift’s Transitional Dressing Is What Fall Outfit Dreams Are Made Of

Story Center by Story Center
November 4, 2025
Reading Time: 5 mins read
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*premium exclusive* new york, ny **web embargo until november 1st, 2025 @ 11 am est** american singer songwriter taylor swift and stylist ashley avignone were spotted enjoying a pre halloween night out in new york. taylor turned heads in an all brown look, while ashley kept it edgy in a black leather jacket and jeans as the pair stepped out for the evening. pictured: taylor swift, ashley avignone backgrid usa 30 october 2025 byline must read: aspn / backgrid usa: +1 310 798 9111 / usasales@backgrid.com uk: +44 208 344 2007 / uksales@backgrid.com *uk clients pictures containing children please pixelate face prior to publication*

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  • Taylor Swift was spotted out with Ashley Avignone in New York City.

  • A few days later, Taylor was photographed out with Gigi Hadid.

  • Her fall outfits seem to revolve around two things: brown boots and miniskirts.


As we transition into fall, so too must our wardrobes. But dressing for transitional weather is far from easy, which is why I like to turn to celebs for inspiration. Luckily, Taylor Swift just gave us two perfect fall outfits back-to-back, so I don’t have to look far.

Taylor has recently been enjoying her post-Life of a Showgirl release victory lap in New York City, where she’s been spotted out and about with friends. Last week, she was photographed exiting Chez Margaux with her friend Ashley Avignone, where she showed off a monochromatic brown ’fit.

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*premium exclusive* new york, ny **web embargo until november 1st, 2025 @ 11 am est** american singer songwriter taylor swift and stylist ashley avignone were spotted enjoying a pre halloween night out in new york. taylor turned heads in an all brown look, while ashley kept it edgy in a black leather jacket and jeans as the pair stepped out for the evening. pictured: taylor swift, ashley avignone backgrid usa 30 october 2025 byline must read: aspn / backgrid usa: +1 310 798 9111 / usasales@backgrid.com uk: +44 208 344 2007 / uksales@backgrid.com *uk clients pictures containing children please pixelate face prior to publication*

GELE – BACKGRID

And on Monday night, Taylor was spotted enjoying a night on the town yet again, this time with Gigi Hadid. They were photographed leaving Zero Bond after dinner, with Gigi sporting leather pants and a mesh top and Taylor once again opting for a miniskirt. Just because we’re getting an hour less of daylight doesn’t mean we’re in tights season just yet!

Based on these two outfits, it seems like Taylor’s fall wardrobe revolves around two staples: the mini and the color brown. Now, I know what you’re thinking: Brown for fall? Groundbreaking. But when done right, you can’t deny that it’s a classic.

Take Taylor’s monochrome outfit, which mixes textures—a brown leather Magda Butrym aviator jacket, a brown Dôen cashmere sweater dress, and brown Manolo Blahnik suede boots. All cohesive, but also with a twist.

Meanwhile, the ’fit she wore out with Gigi combines a classic Auter Italian wool peacoat with a matching mini and two brown snake-print accessories: a Stella McCartney Ryder bag and Stella McCartney Alter stiletto boots.

Brown also happens to pair great with red, a color she’ll likely continue to wear all winter as she cheers on her fiancé Travis Kelce and the Kansas City Chiefs. So who knows—maybe this is a tease of her many NFL game ’fits to come!

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Tags: Ashley Avignonebrown bootsfall outfitsGigi HadidKansas City Chiefsnew york cityTaylor SwiftTravis Kelce
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