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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

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

Cartier ‘Agrafe Herringbone Twisted Necklace’ – $27,250.00

This now marks yet another occasion where Taylor is using her beloved vintage Cartier necklace as a standout jewelry piece to really pop against a black base.

Since acquiring it in May when she debuted it with a simple, black jersey tank dress, she’s also worn it over a high neck LBD and coat in New York. For this occasion, it really stands out against her high neck black top and framed by that vibrant red teddy coat.

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

Stella McCartney ‘Belted Teddy Coat’ – $2,400.00

It’s very fun as we progress deeper into football season that, by extension, we get to see Taylor’s game day fashion change to reflect the actual seasons of the time as well. As a result, we get to see her rocking on-brand Chiefs red via her outerwear like this cozy teddy coat by Taylor go-to Stella McCartney.

The rest of her outfit was sleek and minimal black. The choice to go with a bun also felt like a wise one for me to let the mockneck of her top and the volume of her coat have room to breathe and occupy most of the visual look.

Worn with: VRAI earrings, Cartier necklace, Louis Vuitton skirt, and Stuart Weitzman boots

Photo by Mark Hoffman for the Milwaukee Journal Sentinel

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

Gant ‘240 Mulberry Street Coat’ – coming soon

It’s always helpful (though a mild style faux pas) when Taylor leaves a label on to make identification a little bit easier. (Note that now is a great time to check – and remedy – if the label sleeves and tacking stitches on your coat vents are intact).

This particular navy coat comes from Gant’s Spring/Summer 2024 offerings (set for release in February) as part of their 240 Mulberry Street capsule collection. The brand so dubbed it as an homage to their creative headquarters in NYC, its storefront is also thoughtfully etched into the buttons of this coat.

A new-to-her brand, Taylor has been wearing a lot of Gant’s stunning coats as of late. This coat marks the second time she’s opted for something from their men’s line. It’s anticipated retail price will be about $800USD.

As always, I love when Taylor plays in sharp contrasts: Fabrics, proportions, price points. Here, it’s the interplay between sweet and girlish pieces like a white flouncy dress or schoolgirl-esque loafers with an oversized literally borrowed-from-the-boys jacket that gives the whole thing a chic, prep school vibe.

Worn with: YSL bag and Sézane loafers

Photo by Getty

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

Saint Laurent ‘Cassandra Medium Shoulder Bag’ – $2,895.00

The history behind the ‘YSL’ Cassandra line is an interesting one – it’s actually named after Adolphe Mouron Cassandre, the man who designed the iconic ‘YSL’ logo seen here on the bag’s front.

A part of me can’t help but wonder if Taylor felt kinship to a bag that also shared a name with Cassandra, of Greek myth fame who was doomed to utter prophecies that no one would believe. The poetry of that possibility really strikes me as it feels almost assured that the next (Taylor’s Version) re-record release will be reputation – an album that of course has roots in a famed phone call gone wrong where Taylor told the truth and no one believed her. Too stretchy? Or totally plausible? Would love your thoughts!

Regardless, I love the sleek lines and chain detailing on this bag. But what I love most – if my eyes aren’t deceiving me – is this gorgeous green leather colour.

Worn with: Gant coat and Sézane loafers

Photo by Getty

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

Sézane ‘Jessie Brown Python Print Loafers’ – $265.00

Taylor once again showing off her love of a good repeat, rewearing her Sézane python loafers. In this instance, I think their chunky heel offsets the boxy shape of her coat and dress nicely.

Worn with: Gant coat and YSL bag

Also worn: November 3, 2023

Photo by Getty