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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

Mazin Jewels ‘Toggle Clasp Necklace’ - $89.00
Foundrae 'Belcher Chain Choker’ - $6,365.00

A classic Taylor high/low.

Worn with: Madewell blazer, Jacquie Aiche earrings + Foundrae necklace charm, 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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Happy 1989 (Taylor’s Version) from NYC

Besides debut, 1989 is strangely the era - if not the album - that I have the most biased, sentimental feelings towards. I may not be as stirred by the album’s contents as other Taylor LPs, but the period of time this album was created holds a lot of deeply held emotions for me that have only strengthened in these last few months leading up to 1989 (Taylor’s Version).

I think about the 22 year old me who hailed her first New York City taxi in a mad dash to get to the Empire State Building before midnight.

I think about the 30 year old me who traipsed to the top of that very same building this weekend, stepping out onto the top floor bathed in golden hour light.

I think about all the ways these versions of me are different: Happy. At ease. Thoughtful.
And all the ways we are still the same: Pensive. Quick to laugh. Ambitious.

Here’s to those who are reliving that time period and those living it fully for the first time and all the versions you’ve been in between.


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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


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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

Ralph Lauren ‘Corduroy Cap’ - $69.50

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

Also worn: Out and about September 5, 2023 and Chiefs vs Bears


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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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After Kansas City Chiefs v L.A. Chargers | Kansas City, MO | October 22, 2023

Nike ‘Air Force 1 Low By You’ - $135.00

Based on the unique grey label and gum sole, it appears that Taylor’s Nike sneakers are a custom pair using the brand’s “By You” feature. Hers look to be all white with the only customization being a 'Sport Red’ on the 'Swoosh / Backtab’ feature.

Worn with: Rally House tee


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“IT’S COOL” (x) | October 23, 2023

Reformation ‘Jadey Oversized V-Neck Sweater’ - $298.00

This brown tone feels very on trend for fall colour palettes these days and looks incredibly cozy.

Get the look: H&M, $29.99


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“IT’S COOL” (x) | October 23, 2023

Reformation ‘Winston Blazer in Toffee Plaid’ - $298.00

As someone who takes growing their blazer collection very seriously … this is a delicate situation.

Get the look: H&M, $18.99


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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 sweatshirt, Cartier necklace, Foundrae bracelet + charm, Jacquie Aiche bracelets, and Reformation loafers


THEME