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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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At Arrowhead Stadium | Kansas City, MO | December 10, 2023

Gant ‘240 Mulberry Street Tailored Coat’ – $1,700.00

I mentioned this previously when Taylor last wore a Gant menswear piece (the killa hard launch – if you will) but I knew as soon as I saw those boxy shoulders that this was another mens piece by Taylor’s most recent favourite outerwear brand. And it’s such a smart choice indeed, one that underlines the Americana athleticism of the situation at hand but puts an exclamative “The Man” reminder at the end by opting for a piece from the mens line.

Gant’s 240 Mulberry Street collection is an additional, premium capsule extension of the existing Gant brand – a line meant to honour Gant’s “heritage as pioneers of American Sportswear by taking preppy classics and evolving them into new silhouettes made from the finest fabrics.” See what I said about the perfect fit? Even if the actual fit is intentionally oversized and boxy – another continuing theme for Taylor to unabashedly and confidently take up space as her game day fashion evolves to include bigger silhouettes (thanks to colder weather necessitating wool coats), polished blowouts, and taller heels.

Worn with: Westside Storey vintage sweatshirt, Mazin Jewels + Mejuri rings, Khaite skirt, and Larroude boots

Photo by Nick Wagner for the Kansas City Star

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At Arrowhead Stadium | Kansas City, MO | December 10, 2023

Westside Storey ‘Vintage 90s Chiefs Legends Stitched Spellout Sweatshirt’ – $250.00 (sold out)

A few weeks ago, Taylor reportedly purchased a few thousands of dollars worth of vintage Chiefs pieces from this local KC retailer. I had been wondering just when the home game would come for her to finally break out one of their pieces and it turns out it’s todays against the Bills.

As I suspected it would (I posted a predictions post for Game Day Fashion to the TSS Patreon) – Taylor’s home game style has continued to rely on a base of black with some Chiefs merch as the main piece.

Worn with: Gant coat, Mazin Jewels + Mejuri rings, Khaite skirt, and Larroude boots

Photo by Nick Wagner for the Kansas City Star

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At Lambeau Field | Green Bay, WI | December 3, 2023

Vrai ‘Linked Tennis Earring’ – $1,990.00

As Taylor has been expanding her forays into jewelry stacking, it’s also been fun to see what brands she turns to when experimenting with her jewelry. The last time we saw Taylor wear Vrai was June 2022 at her Tribeca Film Festival appearance.

Worn with: Cartier necklace, Stella McCartney coat, Louis Vuitton skirt, and Stuart Weitzman boots

Photo by Stacy Revere for Getty

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At Lambeau Field | Green Bay, WI | December 3, 2023

Louis Vuitton ‘Strap Detail Mini Wrap Skirt’ – $3,400.00

As we approach the end of the year and I start to turn my gaze backwards on 2023’s fashion to pull together my annual list of Favourite Outfits, in addition to really thinking about what ‘fits to include on my last of faves I also like to think about trending items and patterns that crop up.

All this to say that I feel like in looking back on this year, one such trend might just be the mini skirt. Taylor has worn many over the course of her career, but she’s really been rocking many this fall at least – especially paired with tall boots.

Worn with: VRAI earrings, Cartier necklace, Stella McCartney coat, and Stuart Weitzman boots

Photo by Mark Hoffman for the Milwaukee Journal Sentinel

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At Lambeau Field | Green Bay, WI | December 3, 2023

Stuart Weitzman ‘Vidaland Boot’ – $995.00

Two main things of note with these (incredible) OTK boots.

As noted by the distinctive tie at the back and confirmed to me by the brand these are Stuart Weitzman boots. While Taylor has worn this brand many times over the years, for me they have an unshakeable place solidly in the 1989 Era for their sponsorship of that album’s associated tour and providing many a heel for Taylor to strut in on the 1989 Tour stage. Which feels appropriate given the recent release of 1989 (Taylor’s Version).

Secondly, what I find so fun to watch regarding Taylor’s game day fashion evolution has been observing her growing confidence and power as she grows more comfortable entering these football stadiums as guest and watcher. Her first foray saw her in casual denim shorts and sneaker – unassuming and laidback and sweet. To me, opting for a big coat (wintry weather aside) and tall black leather boots feels powerful and sure. It evokes a voluminous and large presence that cannot be ignored and demands to be seen.

Worn with: VRAI earrings, Cartier necklace, Stella McCartney coat, and Louis Vuitton skirt