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Chiefs vs Patriots | Foxborough, MA | December 17, 2023

Rails custom skirt – not available for purchase

Taylor has been a longtime fan of a plaid mini skirt but it’s also an item that has had a resurgence in her wardrobe these last few months. Skirt-wearing Taylor has two modes: chic and polished with a tucked in top/bodysuit and tall heeled boots or cozily retro with an oversized sweater or sweatshirt and flat shoes. In this case, it’s fun to see when a brand picks up on that love and creates a custom piece to reflect her style with that in mind.

Known best for their plaid shirts, Rails is a brand that Taylor is deeply familiar with – having worn them as early as 2012. Rails VP Linney Warren described Taylor to People as “the ultimate muse for this season’s schoolgirl trend.” Adding, “When we were imagining custom pieces to create for her, we wanted to give her things that she could seamlessly incorporate into her wardrobe — we were thrilled when she chose to style it back to a vintage sweatshirt for the Chiefs game for a bit of nostalgia!”

Given that Taylor’s skirt is custom, it isn’t available for purchase but the Prim skirt is the closest match currently retailing.

Worn with: Vintage sweatshirtKut the Knit beanie, and Mejuri ring

Photo by Kathryn Riley via Getty Images

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Chiefs vs Patriots | Foxborough, MA | December 17, 2023

Vintage ‘Kansas City Chiefs Sweatshirt’ – no longer available

My best guess is this appears to be yet another vintage piece of KC merchandise for Taylor – a similar one pictured here in red. For me, this tactic is fun to see Taylor’s longtime love of vintage fashion (dating back even to 2010-2012) evolve into a way that she can express her recent love of sports (*wink*) while also shopping more sustainably – and often from small businesses.

Worn with: Kut the Knit beanie and Mejuri ring

Photo by Maddie Meyer via Getty Images

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Chiefs vs Patriots | Foxborough, MA | December 17, 2023

Kut the Knit ‘Handmade Beanie’ – $30.00

In addition to acquiring some of Westside Storey’s vintage Chiefs merch, Taylor also opted for one of their cozier handmade items by one of the vintage store’s employees that was gifted to her.

Worn with: Vintage sweatshirt and Mejuri ring

Photo by Maddie Meyer via Getty Images

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Out and about | New York City, NY | December 12, 2023

Gant ‘240 Mulberry Street Leather Trench’ – sold out

This leather trench retailed in very limited quantities as part of Gant’s FW2023 capsule launch so it’s sadly no longer available but it cut a very chic, fashun moment for Taylor that I loved seeing her boldly experiment with.

Worn with: Versace bag, Louis Vuitton + Cathy Waterman jewelry, and Stella McCartney boots

Get the look: Bardot, $270.15

Photo by Gotham via Getty Images

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Out and about | New York City, NY | December 13, 2023

Anine Bing ‘Hilary Faux Fur Jacket’ – $650.00

Layering up against the NYC chill, rather than a long wool coat by the likes of recent outerwear favourites such as Gant – Taylor went glam in a faux fur shrug that, to me, once again just draws similarities to her Midnights Moschino Mayhem with Me moment.

Worn with: Clio Peppiatt dress, Messika earrings, Mazin Jewels necklace, Aquazzura bag and heels

Get the look: Abercrombie, $180.00

Photo by James Devaney via Getty Images

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Out and about | New York City, NY | December 13, 2023

Messika ‘Move Uno Pavé Earrings’ – €4,250.00

I love the sparkle factor of these earrings and their coordination with her tennis necklace. I love the motion property of these line of pieces, where the center diamond stone is actually designed on a track so that it moves within its casing. I love the thought of that tying in to transformation and forward motion.

Worn with: Anine Bing jacket, Clio Peppiatt dress, Mazin Jewels necklace, Aquazzura bag and heels

Photo by Gotham via Getty Images

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Out and about | New York City, NY | December 13, 2023

Aquazzura ‘Atelier Plateau 130 Crystal Embellished Sandals’ – $1,250.00

I admire the consistent styling on display here with how everything from her jewels to her accessories all tie in neatly to the celestial embellishments on her dress.

Worn with: Anine Bing jacket, Clio Peppiatt dress, Messika earrings, Mazin Jewels necklace, and Aquazzura bag

Photo by Gotham via Getty Images

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Out and about | New York City, NY | December 13, 2023

Aquazzura ‘Galactic Crystal Embellished Tote Bag’ – $1,255.00

My very first thought upon seeing this bag resurface was of course to the first time she carried it just a few months ago at after parties following the MTV VMAs. But it incidentally struck me that she’s also once again paired it with platform strappy peep toe heels by the same designer.

Worn with: Anine Bing jacket, Clio Peppiatt dress, Messika earrings, Mazin Jewels necklace, Aquazzura heels

Also worn: 2023 MTV VMA after party

Photo by Gotham via Getty Images