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

Aquazzura ‘Galactic Crystal Embellished Tote Bag’ – $1,255.00

My very first thought upon seeing this bag resurface was of course to the first time she carried it just a few months ago at after parties following the MTV VMAs. But it incidentally struck me that she’s also once again paired it with platform strappy peep toe heels by the same designer.

Worn with: Anine Bing jacket, Clio Peppiatt dress, Messika earrings, Mazin Jewels necklace, Aquazzura heels

Also worn: 2023 MTV VMA after party

Photo by Gotham via Getty Images

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Out and about | New York City, NY | December 12, 2023

Versace ‘Greca Goddess Mini Shoulder Bag’ – $1,525.00

One thing I can appreciate is the consistent use of gold hardware throughout this ‘fit to draw the eye from the top to the bottom of the ensemble. Starting with that lovely golden shadow through to her stacked golden chains, the hardware on this Versace bag, and coordinating chains on her Stella McCartney boots.

Worn with: Gant coat, Louis Vuitton + Cathy Waterman jewelry and Stella McCartney boots

Photo by Gotham via Getty Images

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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 | December 6, 2023

Naeem Khan ‘Zodiac Clutch’ – $1,490.00 (sold out)

This Zodiac clutch originally retailed back in 2018 and was once very notably carried by Meghan Markle. Pictured above is the brand’s ‘Gemini’ constellation but Taylor’s is (of course) her own star sign of Sagittarius.

I love that Taylor has always been a bit of an astrological girly, having previously worn shoes and even released her own necklace merch that reference her zodiac sign.

The metallic coordination with her other gold jewelry totally works here but, of course, one has to wonder if this is simply an example of an accessory playing into her own interests or is a “Mastermind” hint of something else.

Worn with: Charlotte Simone coat and Giuseppe Zanotti heels

Photo by Gotham via Getty Images

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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 4, 2023

Stella McCartney ‘Frayme Crocodile Effect Bucket Bag’ – $1,995.00

Taylor has carried many chain Stella McCartney designs over the years in the forms of various sized bags and even backpacks, namely from Stella’s ‘Falabella’ line – it’s an iconic signature of Stella. I like that the hardware ties in to the jewelry of the ‘fit and the colour continuing the theme of black.

Worn with: Jacquie Aiche necklace + bracelet, Jacquie Aiche + Foundrae earrings, Mazin Jewels rings, Miu Miu skirt, and Stella McCartney boots

Photo by Getty

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Out and about | New York City, NY | November 3, 2023

Mansur Gavriel ’M Frame Box Bag’ – $895.00

In terms of recycling accessories, Taylor previously carried this bag back in May. Back then, she paired it with a fresh white eyelet set by Ralph Lauren and complementary minimalist brown sandals by Aeyde. It’s fun here to see her carry this bag again in a new season and see it work just as well with the fall-like palette of her outfit today.

Speaking of things we’ve seen before – if I had to guess, Taylor’s security guard in the background here is also carrying her very first Gant piece we saw last month – their cropped wool blazer jacket.

Worn with: Gant sweater, The Row pants, and Sézane loafers

Also worn: May 24, 2023

Get the look: Matt & Nat, $110.00

Photo by Gotham ℅ Getty

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Out and about | New York City, NY | October 27, 2023

Hunting Season ‘The Trunk in Satin w/ Tassels’ – $925.00

All of Taylor’s fashion hallmarks were on display here with this outfit: 1) An enviable high/low mix by pairing high street like Madewell with designer like Gianvito Rossi 2) Repeating pieces like her Acne Studios corduroy skirt, last seen October 2022 3) Supporting smaller, indie designers like NY-based brand Hunting Season. Which also, in my opinion, has a not-too-farfetched reference to “I Know Places”.

Worn with: Madewell blazer, Jacquie Aiche earrings + Foundrae necklace charm, Mazin Jewelry necklace + Foundrae chain, Acne Studios skirt, and Gianvito Rossi boots

Photo by Getty

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Out and about | New York City, NY | October 26, 2023

Tod’s ‘Logo Plaque Leather Crossbody Bag’ – $2,525.00

Despite the competing shades of brown, this is still such a great copy + paste fall ‘fit for me. The emblem knit layered over a crisp white button up is so preppy chic to me. And I love the combination of a “dress up” and “dress down” accessory factor via the competing laidback baseball cap and killer tall boots (which I’m so glad to see are having a fashion trend resurgence).

Worn with: Stella McCartney shirt, Ralph Lauren hat, and Prada boots

Also worn: October 19, 2023