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Out and about | New York City, NY | April 20, 2023

Stella McCartney ‘Rectangular Sunglasses’ – $310.00
Stella McCartney ‘Frayme Medium S-Wave Flap Shoulder Bag’ – $1,530.00
Simkhai ‘Pandora Embellished Skirt’ – $390.00
Chanel ‘Back to College Loafer’ – $1,350.00

This skirt, when paired with a very closely matched top (getting shades of black to match is so hard), gives the appearance of a dress when it is actually sneaky separates.

Taylor has rocked many all black ensembles over the years and it’s always been the chicest complement to her red lip.

The repeated motif of chains here could certainly have a more symbolic read, but I like it purely as a styling detail that keeps the outfit cohesive but distinct.

Taylor has long been a lover of a loafer and worn many over the years. Leather, suede, heeled. The choice to wear Chanel, on the other hand, is more unfamiliar territory. She’s worn the French house often enough when styled for photoshoots, but rarely in her street style. I can actually only think of two Chanel footwear instances in all my years documenting her fashion. A pair of black leather oxfords (worn multiple times in 2012 – it has its own dedicated tag here) and one pair of cap toe bow heel pumps (December 2014).

Get the look: Sunglasses, $14.89 / Skirt, $62.13 / Loafers, $64.43

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Attending the premiere of The Banshees Of Inisherin | New York City, NY | October 10, 2022

Stella McCartney ‘Single Breasted Oversize Blazer’ – $1,495.00

Taylor is really gravitating towards boxier/oversized silhouettes these days. With a pair of wide leg pants like these, I think either committing to an intentionally oversized/baggy look is very on trend as of late.

My personal preference would be to offset a wide leg trouser like this with a more tailored blazer – but I’m also not one to look a gift blazer in the mouth.

Worn with: Etro bag and Prada loafers

Get the look: Aqua, $70.80

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Out and about | Beverly Hills, CA | June 29, 2022

Stella McCartney ‘Cat Print Hoodie’ – $550.00 (sold out)

*Taylor very clearly did not want to be seen in these images. In keeping with TSS identification principles, I’ve cropped her face to retain focus on the clothes for those interested in such details.

I suspect Taylor’s love of Stella’s clothes will stick around for quite some time if the designer keeps putting cats on things.

Worn with: Ralph Lauren bag and Juju sandals

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Benjamin is 22 in cat years. | December 27, 2021

Stella McCartney ‘The Beatles Get Back Tie Dye Hoodie’ – $895.00

A double English moment! Just as Taylor collaborated with British designer Stella McCartney to create an exclusive line of merch for her album Lover, Stella also created a line of Beatles merch in – dare I say – Lover-esque colours. Given Stella’s obvious connection to both Taylor and The Beatles, this is a really sweet moment.

Get the look: Topman, $56.00

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RED (Taylor’s Version) | November 12, 2021

Stella McCartney Fall 2020

In a new photo used in the RED (TV) album booklet, we spy Taylor wearing yet another Stella coat. I personally like this warm cream colour better than the original black presented on the runway.

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RED (Taylor’s Version) | June 18, 2021

Stella McCartney coat – not available for purchase

/screams in RED.

Given that this coat made its first appearance in the evermore album photoshoot begs the question … did she know when she shot this that this was the plan for the cover?

Worn with: Cathy Waterman ring and Janessa Leone hat

Also worn: evermore album photoshoot