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Out and about | New York City, NY | May 22, 2023

Ralph Lauren ‘Calfskin Welington Shoulder Bag’ – $1,690.00

Taylor has worn and loved many a Ralph Lauren cognac brown saddle bag over the years. This new ‘Welington’ style is a more oblong one to her collection and coordinates nicely in a sandwich styling moment with the brown tone of her sandals.

Worn with: R13 shirtR13 shorts, and A. Emery sandals

Photo by Gotham ℅ Getty

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Out and about | New York City, NY | May 22, 2023

R13 ‘Crossover Denim Shorts’ – $365.00

With Eras Tour shows in MetLife scheduled for this weekend, I had anticipated seeing Taylor out and about in the city. The only question was – how soon would that be off the heels of her Gillette dates?

The answer was right away.

Worn with: R13 shirt, Ralph Lauren bag, and A. Emery sandals

Get the look: AE, $49.95

Photo by Gotham ℅ Getty

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Leaving Electric Lady Studios | New York City, NY | May 18, 2023

Stella McCartney ‘Tan Falabella Box Wicker Shoulder Bag’ – $990.00 (no longer available)

Taylor has carried quite a few different Stella ‘Falabella’ styles over the years. Including backpacks (black and leopard), quilted styles, limited edition graphics, and even an animal carrier.

This particular ‘wicker’ style is an older one from 2018 that Taylor first wore (incidentally) during a string of candids leading up to her MetLife shows on the reputation Tour back in July 2018.

Worn with: Magnolia Pearl jeans and The Row sandals

Also worn: July 15, 2018

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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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Out to dinner | New York City NY | April 17, 2023

Agolde ‘Criss Cross High Rise Jeans’ – $235.00 $164.00

Taylor is typically trend agnostic when it comes to her style. She largely eschews “it” bags or of the moment silhouettes in favour of pursuing her own thing (in support typically of her latest era).

So it’s very fun (and intriguing) to see Taylor rock trendy 90s-adjacent baggy denim, chunky gold jewelry, and thick sole.

Worn with: The Row boots

Get the look: Abercrombie & Fitch, $59.99