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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 27, 2023

Gianvito Rossi ‘Ankle Boots’ – $1,220.00 $850.00

Lovingly, it is never truly a fully ‘Taylor’ outfit without an element of quirk or something slightly ‘off’ to make it interesting and ‘her’. I perhaps would have gone with this pair of boots in black, but Taylor opted for another rich colour to add to the palette of the outfit.

Worn with: Madewell blazer, Jacquie Aiche earrings + Foundrae necklace charm, Mazin Jewelry necklace + Foundrae chain, Hunting Season bag, and Acne Studios skirt

Photo by Getty

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

Jacquie Aiche ‘Marquise Center Flying Thunderbird Drop Stud’ – $4,550.00
Jacquie Aiche ‘3 Graduated Teardrop Sophia Diamond Chain Double Stud’ – $3,200.00
Foundrae ‘Forever & Always A Pair Oval Pendant’ – $1,450.00

Worn with: Madewell blazer, Mazin Jewelry necklace + Foundrae chain, Hunting Season bag, Acne Studios skirt, and Gianvito Rossi boots

Photo by Getty

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

Madewell ‘Larsen Blazer in Leather’ – $548.00

This is a great example of Taylor dressing to formula. While we haven’t seen her in this exact combination before, to me it struck a similar note to her KC Chiefs vs NY Jets game ensemble which also comprised of a few, key similar components: Statement leather topper, simple black top, contrasting short bottoms, complementary leather boots.

While that outfit felt like a hot summer evening outfit, the colour palette here firmly establishes it into ‘fall’ territory.

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

Photo by Getty

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

Acne Studios ‘Corduroy Skirt’ – $380.00

Taylor is really setting the bar for this year’s fall outfits. All the warm brown and black tones in rich and contrasting materials is very good eye candy.

Worn with: Madewell blazer, Jacquie Aiche earrings + Foundrae necklace charm, Mazin Jewelry necklace + Foundrae chain, Hunting Season bag, and Gianvito Rossi boots

Also worn: Midnights Mayhem with Me

Photo by Getty

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

Ralph Lauren ‘Corduroy Collar Cotton Field Jacket’ – $762.00

If I were to have picked a piece of outerwear by any brand to complement the equestrian energy of this ‘fit, it would have been Ralph Lauren – so I’m delighted that this toffee coloured field jacket is a Polo by RL piece.

I’ll also say that while previously the two tone mix of browns sans coats wasn’t entirely sold on me that now with the addition of a third brown shade that the mixture now feels more ‘complete’ and robust – like a true, intentional fall-leaning palette.

Worn with: Stella McCartney shirt, Tod’s bag, and Prada boots

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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