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Eras Tour Film premiere | Los Angeles, CA | October 11, 2023

Giuseppe Zanotti ‘Intriigo Strap Sandals’ – $950.00

As a lover of a minimalist ankle strap sandal, my eye happily went to this pair of Giuseppe Zanotti heels. While I do personally love a tonal moment, looking at the lewk as a whole, I also can totally picture a champagne or silver pair of heels to complement her tennis jewelry and finish the ‘fit off on a brighter, complementary shimmery note.

Worn with: Oscar de la Renta gown, Cartier necklace + Anabela Chan bracelets, and Cartier studs + Cathy Waterman + Akillis + Anabela Chan rings

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Eras Tour Film premiere | Los Angeles, CA | October 11, 2023

Oscar de la Renta ‘Cutout Floral Gown’ – $11,990.00 $5,995.00

In my predictions post for this premiere on the TSS Patreon I selected a different dress by Oscar de la Renta (a longtime favourite designer of Taylors) and noted that my ideal styling with said gown would be a “red lip and pinned faux bob with tons of bangles and chandelier diamond earrings … for an old Hollywood glam feel.”

Needless to say, I support and love this outing.

It’s dramatic and ladylike while also honouring and extending the #1989Blue precedent she set during the final stages of the U.S. 2023 leg of the Eras Tour. Dressing to a colour palette is a perfect connector and reminder to bridge both the event at hand of the concert tour movie and her most pressing upcoming record with 1989 (Taylor’s Version) set to release on October 27.

All in, this is a beautiful gown and perhaps one of her best appearances ever. The elegant styling (dainty rings and eye-popping matching diamond tennis necklace and bracelet) were the perfect choices. And maybe I’m just jealous that Taylor is someone who can pull off blue eyeshadow (any other brown eyed girls who were told that blue makeup would make your eyes pop and subsequently did not look like Taylor Swift when you tried a powder blue shadow look? anyone? just me?).

Designer Fernando Garcia also noted during the Resort 2023 collection’s presentation that “cut-outs have become a go-to for our customer”. The ones on this gown feel like an organic nod to the spliced crop tops that were signature to the original 1989 fashion run in 2014. But here, they’re more organic and integrated into the design – a natural part of fully blossoming some might say. And if you missed the subtle cut-out nod, there’s always the faux bob that might double take you into believing you were back in 2014/15 and also nods to the messy, slightly undone style seen on the 1989 TV cover.

As backstory, it should surprise no one that this particular collection happened to debut on June 13, 2022 at (where else) the New York Botanical Garden.

Worn with: Cartier necklace + Anabela Chan bracelets, Cartier studs + Cathy Waterman + Akillis + Anabela Chan rings, and Giuseppe Zanotti heels

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

Louis Vuitton ‘Camera Box Bag’ – $3,450.00

For those perhaps not aware or even blown away by Taylor’s ongoing carrying of this cute little LV bag (understandable given repeating fashion in the celeb world is typically a Kate Sanders-worthy no no) – it’s a key part of what I love about Taylor’s fashion is just how often she keeps things in her closet and rotates them. Back in the original 1989 era, she’d carry a nude bag of choice (often D&G or Prada) for months on end before switching to something new.

Worn with: Still Here hat, Free People shirt, Free People socks, and New Balance x Ganni sneakers

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

Still Here ‘Dad Cap in Khaki’ – $45.00

Switching gears completely from the weekend where she was at a sporting event to looking more sporty while out in NYC.

The mix/match of luxury (Louis Vuitton), accessible high street (Free People), casual yet unique (New Balance x Ganni), and local indie designers (Still Here) is the exact epitome of Taylor’s approach to style. In my opinion, it’s this careful balance that makes her style so interesting and fun to watch and observe (and imitate).

Worn with: Free People shirt, Louis Vuitton bag, Free People socks, and New Balance x Ganni sneakers

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

Free People ‘Daydreamer Shania Twain Any Man Of Mine Tee’ – $88.00

The combination here of evoking a few different icons of fashion (peak fall athleisure Princess Di) and genre busting (the iconic and incomparable country/pop of Shania Twain) plus a Karma-worthy accessory denoting that she is Still Here (plus that not so subtle reminder to any man who may enter her life) … that’s some impeccable candid styling.

Worn with: Still Here hat, Louis Vuitton bag, Free People socks, and New Balance x Ganni sneakers

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Out and about | New York City, NY | October 1, 2023

Gant ‘240 Mulberry Street Relaxed Leather Shirt’ – coming soon (pictured similar)

I’ve mentioned before being a fan of what I call ‘sandwich’ styling – which is to have two similar elements in an outfit bookend a contrasting element. To sandwich is to imbue an outfit with balance. In this case, the blue of her crystallized denim shorts is anchored by a lot of black accessories. Including this edgy leather shirt by #Gant from their upcoming exclusive FW 2023 collection dubbed ‘240 Mulberry Street’ – named after the address of their creative headquarters in NYC.

The impact of this in the context of sandwich styling also works in multiple regards. Proportionally, the longer length of both the jacket and her Louboutin boots (also leather, upping the sandwichification of the ‘fit) offsets the short hem of her shorts. In short – I loved this styling.

You may recall that last week Taylor actually popped into the very same Gant NYC store to purchase a coat on a whim while out with friends. I’d hazard a guess the team was so delighted they sent through this coat as thanks.

Worn with: Logan Hollowell necklace, Area shorts, and Christian Louboutin boots

Get the look: ASOS, $79.99 / Abercrombie, $90.00

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At MetLife Stadium | East Rutherford, NJ | October 1, 2023

Logan Hollowell ‘Queen Cuban Choker w/ Pavé Diamond Trillion Toggle’ – $7,995.00

Of Taylor’s recent gold jewelry additions to her collection this particular front clasp trillium choker might be one of my favourites for its simplicity but special details and meaning. The brand notes the individualism inherent to the trillion toggle design – “the three sided sort of versatility in a triangle captures themes of magic, wonder and creativity in its meaning. None of the other basic shapes offer this kind of inherent duplicity.”

Worn with: Gant jacket, Area shorts, and Christian Louboutin boots

Also worn: September 21, 2023