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Out and about | New York City, NY | December 8, 2023

Gant ‘Shearling Jacket’ – $1,700.00
Guest in Residence ‘Waffle Polo in Hunter’ – $445
.00 (sold out)
Miu Miu ‘Pleated Check Mini Skirt’ – sold out
Calzedonia ‘Sheer 40 Denier Tights’ – $10.00 $5.00 (on sale) [Thanks Anon!]
Saint Laurent ‘Le 5 à 7 Hobo Bag’ – $2,650.00
Reformation ‘River Boot’ – $478.00

Taylor’s love of Gant’s outerwear continues – this time in an oversized shearling jacket that’s a spin on a classic aviator style and feels very cozy wintery and stands as a nice proportional contrast to her (repeat) Miu Miu skirt we previously saw her wear while on a date with Travis in Argentina when one of her shows was rained out and postponed. Taylor also owns this particular mini in another plaid check print.

One thing that I feel like Taylor does often is create interesting, unexpected, colour palettes with her outfits. It’s something she’s done for a long time that feels very classically ‘her’. If it were me, I would have done a sandwich style moment and opted either for the same camel tone as her Saint Laurent bag in both her carry item and boots or perhaps even both a dark chocolate brown to tie into the piping on her Gant jacket. As-is, her ‘ruby’ Reformation boots create a colour (albeit Christmas-y) contrast.

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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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Performing at Carole King’s Rock & Roll Hall of Fame Induction | Cleveland, OH | October 30, 2021

Saint Laurent ‘Single Breasted Blazer’ – $2,043.53

Worn with: Sarah Regensburger jumpsuit + Greta Constantine jumpsuit, Aaryah earrings, Djula/Melinda Maria/Graziela jewelry,and Louis Vuitton boots

Get the look: ASOS, $36.00

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BBC Radio 1 Live Lounge | September 2, 2019

Saint Laurent ‘Lou Lou Ankle Boots’ – $1,095.00 $438.00

While I didn’t approve of the last time Taylor wore a bold pair of ankle boots by Saint Laurent, this fares much better paired with this outfit. Namely because the bright fuchsia tones speak back to the embellishments on her blouse. 

In a way, they also sort of bring a modern cowgirl vibe to the outfit given the sheer blouse and high-waisted leather shorts. The proportions of the outfit work much better with an ankle boot look over a full length jumpsuit. 

Worn with: Saint Laurent blouse + shorts and Versace belt

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BBC Radio 1 Live Lounge | September 2, 2019

Saint Laurent ‘Lou Lou Ankle Boots’ – $1,095.00 $438.00

While I didn’t approve of the last time Taylor wore a bold pair of ankle boots by Saint Laurent, this fares much better paired with this outfit. Namely because the bright fuchsia tones speak back to the embellishments on her blouse. 

In a way, they also sort of bring a modern cowgirl vibe to the outfit given the sheer blouse and high-waisted leather shorts. The proportions of the outfit work much better with an ankle boot look over a full length jumpsuit. 

Worn with: Saint Laurent blouse + shorts and Versace belt

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BBC Radio 1 Live Lounge | September 2, 2019

Saint Laurent ‘Embellished Leather Shorts’ – $2,490.00

Taylor delivered one of her best Live Lounge performances to date with a six song set. I loved every last choice. 

Worn with: Saint Laurent blouseVersace belt, and Saint Laurent boots

Also worn: “Lover” music video

Get the look: Express, $39.99

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BBC Radio 1 Live Lounge | September 2, 2019

Saint Laurent ‘Embellished Leather Shorts’ – $2,490.00

Taylor delivered one of her best Live Lounge performances to date with a six song set. I loved every last choice. 

Worn with: Saint Laurent blouseVersace belt, and Saint Laurent boots

Also worn: “Lover” music video

Get the look: Express, $39.99