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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

The Row ‘Constantine Gown’ – $2,490.00 $1,245.00

To support her friend Emma Stone at the premiere of her film Poor Things, I love that Taylor went chic but glam in all black – a decision I feel is rarely a bad one. She kept things simple in a slinky, floor-length black dress by The Row which is fast becoming one of her most worn brands this year.

Worn with: VRAI earrings, Charlotte Simone coat, Naeem Khan clutch and Giuseppe Zanotti heels

Photo by Gotham via Getty Images

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Out and about | New York City, NY | December 5, 2023

VRAI ‘Round Solitaire Stud’ – $500.00
VRAI ‘Trillion Ear Jacket’ – $650.00
Jacquie Aiche ‘Small Pave Emerald Oval Eye Diamond Necklace’ – $6,300.00
Louis Vuitton ‘Blossom Ring’ – $2,450.00

Worn with: Stella McCartney coat and skirt, Sheertex tights, Jimmy Choo x Jean Paul Gaultier heels

Photo by James Devaney via Getty

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Out and about | New York City, NY | December 6, 2023

Charlotte Simone ‘Penny Faux Fur Coat’ – £400.00

There’s a certain, “I killed a man just to walk on his grave in my heels” energy to this look that I equal parts admire and fear.

Interesting to note here that this is a new-to-her designer for Taylor whose trio of signature style pillars I’d neatly summarize as: Repetition, High/Low Price Pairing, and Indie Designers.

The third point here is the case with Charlotte Simone, a London-based brand that focuses on sustainability and small-scale production.

Worn with: Naeem Khan clutch and Giuseppe Zanotti heels

Photo by Gotham via Getty Images

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Out and about | New York City, NY | December 6, 2023

Giuseppe Zanotti ‘Lilibeth Slingback Stiletto Sandals’ – $750.00

Maybe she’s trying out a shoe capsule. I kid. But this does mark the third time Taylor has worn these v chic Giuseppe slingbacks – the most recent being at the RENAISSANCE London film premiere.

Worn with: Charlotte Simone coat and Naeem Khan clutch

Also worn: 2022 MTV Europe Music Awards and RENAISSANCE premiere

Photo by Gotham via Getty Images

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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 | December 5, 2023

Sheertex ‘Modern Diamond Sheer Tights’ – $99.00 $35.00 (on sale)

There are truly few things that give me fashion flashback in Taylor’s closet staples like a pair of designed tights which lift me all the way to her earliest days even through to now. When wearing designed tights like these, Taylor’s also not been one to be afraid of layering them with other patterns – like the plaid you see here.

Also note the signature high/low on display here in terms of designers.

Worn with: Stella McCartney coat and skirt, VRAI + Jacquie Aiche + Louis Vuitton jewelry, Jimmy Choo x Jean Paul Gaultier heels

Photo by James Devaney via Getty

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Out and about | New York City, NY | December 5, 2023

Jimmy Choo x Jean Paul Gaultier ‘Leather Wedge Pumps’ – $2,450.00

One of Taylor’s go-to heel brands is Jimmy Choo so opting for this brand doesn’t necessarily come as a surprise, but what does is the bolder choice to go with this limited edition shoe co-designed with JPG.

The design takes what’s otherwise a regular pointed black pump and gives it a twist with a plexi wedge heel – modernizing the stiletto and also giving it an artistic form.

The pointed toe is also not typically something that Taylor opts for, but its elongated silhouette once again (to me) calls back to that Miss Americana red carpet outing where she also (again, rare occasion) opted for pointed toe boots. Given that in the last week we’ve seen multiple high profile business accomplishments in the press by Taylor (highest grossing tour by Billboard, Most Intriguing Person by People, 5th most powerful woman in the world by Forbes), it doesn’t feel like a stretch to me that she’d be revelling in a shoe that feels more powerful by extension and business-y.

Another fun fact? The wedge was designed to reference the “iconic architectural landmarks of the two brands’ home cities: Paris with the Tour Eiffel and London with Big Ben asymmetrically encased inside each heel.” An interesting homage.

Worn with: Stella McCartney coat and skirt, VRAI + Jacquie Aiche + Louis Vuitton jewelry, and Sheertex tights

Photo by James Devaney via Getty

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Out and about | New York City, NY | December 5, 2023

Stella McCartney ‘Frayed Checked Wool Blend Tweed Mini Skirt’ – $975.00

Just the other day in stories I was talking about the history of Taylor and mini skirts and how – especially as we approach the end of 2023 – that this year has seen quite a revival for them in her candid fashion.

While it’s fun to see Taylor’s style come to fruition in the moment, I very much think that consideration for an ‘era’ as a whole can really only be done in hindsight once we have a birds eye view of the time period in order to be able to really pull out trends, commonalities, and patterns.

In this current moment, a wool tweed mini (esp paired with designed tights – another closet staple Taylor has a long history with) feels preppy, smart, and wintery. Almost Gossip Girl-esque!

Worn with: Stella McCartney coat, VRAI + Jacquie Aiche + Louis Vuitton jewelry, Sheertex tights, Jimmy Choo x Jean Paul Gaultier heels

Photo by James Devaney via Getty

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Out and about | New York City, NY | December 5, 2023

Stella McCartney ‘Double Breasted Wool Blend Tweed Coat’ – $2,900.00

While Stella McCartney is very much a Lover era brand (courtesy of Taylor’s fashion collaboration with the brand), a matching set like this gives me #1989 flashbacks – an era known predominantly for the power of a co-ordinated ‘fit.

Still riding the high of 1989 (Taylor’s Version) this very much to me feels like an elevated, business-esque, modern take on the crop tops and skirts of her 2014 self. But built for cooler weather.

It also to me harkens back to her neck to foot plaid look for the Miss Americana premiere at Sundance which also featured a wool check plaid.

Worn with: Stella McCartney coat, VRAI + Jacquie Aiche + Louis Vuitton jewelry, Sheertex tights, Jimmy Choo x Jean Paul Gaultier heels

Get the look: Abercrombie, $154 (on sale)

Photo by James Devaney via Getty