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Out and about | New York City, NY | October 15, 2023

Alessandra Camilla Milano ‘Blue Rain Diamond Cuffs Drop’ – $2,490.00

Ever the type to mix metals, Taylor wears the yellow gold version of this earring after wearing it in white gold last month at the MTV VMA after party.

Worn with: Maria Tash earrings, Jean Paul Gaultier top, Balenciaga corset, Roger Vivier bag, Khaite skirt, and Louis Vuitton boots

Also worn: MTV VMA 2023 after party

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Out and about | New York City, NY | October 15, 2023

Roger Vivier ‘Viv’ Choc Bag in Leather’ – $3,995.00

In terms of bag style, Taylor will typically opt for a cross-body worn on her right shoulder or a shoulder bag propped on the top of her forearm. So in an instance like this, it’s fun and notable to see her actually tote a shoulder bag where its name implies.

I do love the rich tones of this bag (the red speaks to me personally) but I wouldn’t have minded it in the black shade that it comes in.

Worn with: Maria Tash earrings, Alessandra Camilla Milano earrings, Jean Paul Gaultier top, Balenciaga corset, Khaite skirt, and Louis Vuitton boots

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Out and about | New York City, NY | October 15, 2023

Louis Vuitton ‘Star Trail Boots’ – $1,760.00 (similar)

One thing about Taylor is that she loves a chunky boot and has for years. She’s worn many iterations of an edgy black lace up combat-style boot.

This particular pair has a long history in Taylor’s closet, hailing from the brand’s Fall 2016 collection which Taylor happened to wear the night before the Met Gala 2016 when she was co-chair of the event as a guest of LV.

Worn with: Maria Tash earrings, Alessandra Camilla Milano earrings, Jean Paul Gaultier top, Balenciaga corset, Roger Vivier bag, and Khaite skirt

Also worn: May 1, 2016

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Out and about | New York City, NY | October 15, 2023

Jean Paul Gaultier ‘Fleurs Petit Grand Print Mesh Top’ – $320.00

JPG is well known for their figure forming mesh pieces. I am well known for my love of Taylor wearing green. In this particular instance, I think we all could have done a bit better.

One of their most memorable being their horizontal stripe illusion motif that recurs as a mainstay in their designs spanning decades. This particular top is from the French brand’s Summer 2023 collection titled ‘Flowers’ – drawing inspiration from its 2000s archives.

In theory, the decision to style simply here with a black skirt and boots was the right call but I think a full tuck of the shirt and a more streamlined, taller pair of boots would have made a huge difference.

Worn with: Maria Tash earrings, Alessandra Camilla Milano earrings, Balenciaga corset, Roger Vivier bag, Khaite skirt, and Louis Vuitton boots

Get the look: Free People, $74.29

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Attending SNL after party | New York City, NY | October 14, 2023

Versace ‘Medusa Detail Corset’ – $1,750.00

Taylor’s second corset/bustier moment in the last week. I personally love the combination of something more inherently sensual and feminine combined with menswear and tailoring. To me it exudes a level of comfort and confidence and ease that’s powerful and admirable.

The gold strap detailing also is a great tie in to her latest approach to more is more with gold jewelry – tones of that also layered her throughout the outfit to create a consistent level of shine throughout.

The iconic Medusa motif is one signature to Versace, present as one of the house’s most key design pieces. It’s inclusion here is a double whammy reference to the Eras Tour, where Versace opens her concert looks, and also continues to underline a story of feminine reclamation, strength, and power.

And, well, the snake backstory of it all is a bit on the nose isn’t it.

Worn with: Maria Tash earrings, Gant coat, Mazin Jewels necklace, Aupen bag, and Greymer sandals

Get the look: Urban Outfitters, $44.99

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Attending SNL after party | New York City, NY | October 14, 2023

Aupen ‘Nirvana Bag’ – $340.00

Taylor previously carried this braided bag at Jack Antonoff’s wedding. It does a great job of marrying the black and gold elements present through the rest of the ‘fit while also balancing the straighter lines of the bustier and slacks with the organic texture of its handle.

Worn with: Maria Tash earrings, Gant coat, Mazin Jewels necklace, Versace corset, and Greymer sandals

Also worn: Jack Antonoff’s wedding

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Attending SNL after party | New York City, NY | October 14, 2023

Gant ‘Houndstooth Wool Trench’ – $825.00

How does one dress for a hard launch? For an outing that all parties involved would know would garner headlines, it’s a lot to ask of an outfit.

Stepping out in NYC to make a surprise appearance on SNL in support of Ice Spice, Taylor attended the show’s after parties with Travis Kelce.

Her outfit of choice falls in line as of late with her tendency for luxe neutrals and suiting. This particular choice of outerwear is her third time in recent weeks to opt for Gant – the most recent being her MetLife outfit at the Chiefs v Jets game courtesy of a leather shirt jacket.

Gant is a brand steeped in the American collegiate prep fashion and, since the 70s and changing trends post-war, has had quality clothes informed by athletics and comfort at its core. According to the brand, “As sports activities influenced many creative tailoring features, the demand for a comfortable look continued to spread. GANT shirts helped define the casual-yet-smart look”. What better brand to turn to that nods to both Americana and athleisure to kick off the official public start to a relationship with an NFL player.

The added level of intrigue is Taylor’s choice of outerwear here is from the brand’s menswear line. Pairing it with ultra feminine pieces (a bustier, heels) and wearing it casually one shoulder feels simultaneously powerful yet effortless.

The jacket around her shoulders? Hers.
And in case you forgot, she is The Man.

What a message.

Worn with: Maria Tash earrings, Mazin Jewels necklace, Versace corset, Aupen bag, and Greymer sandals

Get the look: Steve Madden, $176.47

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At Arrowhead Stadium | Kansas City, MO | October 12, 2023

Prada ‘Black Lace Up 110 Military Boots’ – $1,205.00

Despite not having HQ images of Taylor’s full ensemble (which I’d love!), I still feel reasonably confident on these boots which I suspect are an older pair by Prada that Taylor previously wore in September 2019 while on stage during her City of Lover concert.

Worn with: WEAR by Erin Andrews jacket and Balenciaga corset

Also worn: City of Lover concert