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

Stella McCartney ‘Oversized Cotton Rugby Polo Shirt’ – $850.00

This dress is so comically Taylor. From the designer choice to feeling like an evolution of her preppy schoolgirl style that’s been a mainstay aesthetic in her outfit repertoire since Fearless days. But this version takes styling cues from the Stella runway, wearing this oversized shirt as a mini dress with tall boots.

The horse girl energy between the RL cap and the equestrian take on a school uniform emblem are also very Taylor.

A fun note about this particular Stella collection is its further push towards sustainability with most of the pieces taking material sourcing from upcycled or overstock fabrics.

Worn with: Ralph Lauren hat, Tod’s bag, and Prada boots

Get the look: H&M, $34.99

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

Prada ‘Leather Knee High Boots’ – $1,040.00

For anyone who would like to continue to deny the resurgence of 1989-era clothes, I present to you a pair of Prada boots not seen since January 1, 2015.

Between the two occasions we’ve seen these boots, I’m a much bigger fan of this iteration which feels far more pared back and – simply speaking – cooler.

Worn with: Stella McCartney shirt, Ralph Lauren hat, and Tod’s bag

Get the look: Journee Collection, $90.99

Also worn: January 1, 2015

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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

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At Arrowhead Stadium | Kansas City, MO | October 22, 2023

Erimish ‘Number + Heart Custom Bracelet’ – $21.00

Nice to see Taylor wearing local! Her custom ‘❤️87❤️’ bracelet is by Missouri-based #Erimish. This is apparently a favoured business by Randi Mahomes, mom of KC Chiefs quarterback Patrick and likely a gift from her!

Worn with: Ellie Mae sweatshirtCartier necklaceFoundrae bracelet + charm, Jacquie Aiche bracelets, and Reformation loafers

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At Arrowhead Stadium | Kansas City, MO | October 22, 2023

Jacquie Aiche ‘Evil Eye Bracelet’ – $5,250.00
Jacquie Aiche ‘7 Diamond Kate Smooth Bar Bracelet’ – $5,950.00

Taylor has been wearing a lot of Jacquie Aiche jewelry lately – from necklaces, to bracelets, to body jewelry. These two particular wrist chains she’s worn previously over the summer and at the 2023 MTV VMAs.

Worn with: Ellie Mae sweatshirtCartier necklace, Foundrae bracelet + charm, and Reformation loafers

Also worn: September 30 2023 and 2023 MTV VMAs

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At Arrowhead Stadium | Kansas City, MO | October 22, 2023

Foundrae ‘Heavy Belcher Bracelet’ – $3,440.00
Foundrae ‘Enamel Miniature Medallion’ – $995.00

To complement her necklace version of this particular chain, Taylor can now add the bracelet iteration to her ever growing jewelry collection with a matching heart pendant from #Foundrae’s love collection – a celebration of the “seven classic types of love”.

Speaking of heart feels – on Taylor’s right wrist she had a few other gold chains in addition to a more personal and handmade piece with beads spelling out ‘❤️87❤️’, representing a certain tight end’s jersey number.

Worn with: Ellie Mae sweatshirt, Cartier necklace, Jacquie Aiche bracelets, and Reformation loafers

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At Arrowhead Stadium | Kansas City, MO | October 22, 2023

Reformation ‘Lolita Platform Loafer’ – $348.00

Based on Taylor’s longtime love of the brand, my best guess from photos is Taylor’s platform loafers are these by Reformation.

The combination of a pleated skirt and a heeled loafer bring me back to Speak Now days for Taylor – it’s a youthful leaning fashion combination for Taylor that feels core to her feminine style and I love here that there’s an athletic twist to her tried and true schoolgirl style.

Worn with: Ellie Mae sweatshirt, Cartier necklace, Foundrae bracelet, and Jacquie Aiche bracelets

Get the look: Sam Edelman, $140

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At Arrowhead Stadium | Kansas City, MO | October 22, 2023

Cartier ‘Juste un Clou Necklace’ – $15,570.00

One of Cartier’s signature designs is the ‘Juste un Clou’ – inspired by the nail. Taylor is relatively new to wearing Cartier, having only just recently worn one of their vintage necklaces this summer. The Juste un Clou is designed with the concept of breaking convention in mind, encouraging the wearer to be “original, independent, fearless, and free.”

I personally love the mix of casual sports attire with high end stacks on stacks of jewelry to “dress up” an otherwise casual ensemble.

Worn with: Ellie Mae sweatshirt, Foundrae bracelet, Jacquie Aiche bracelets, and Reformation loafers

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At Arrowhead Stadium | Kansas City, MO | October 22, 2023

Ellie Mae Studios ‘Vintage Kansas City Chiefs Sweatshirt’ – sold out

Taylor’s continued M.O. for Chiefs home games has been cute casual and centered on comfortable Chiefs merch. This pairing of a cozy sweatshirt and pleated skirt feel very much in her wheelhouse and something we’d see her wear a variation (less football-ified) version of as a street style candid outfit.

Worn with: Cartier necklace, Foundrae bracelet, Jacquie Aiche bracelets, and Reformation loafers