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Out and about | New York City, NY | November 4, 2023

Stella McCartney ‘Ryder Alter Sporty Mat Boots’ – $1,850.00

This feels like a great example of why proportions and silhouette matter.

In terms of items and the ‘fit concept this has all the makings of a great copy + paste for me: Black, sandwich styling, killer boots. But in execution, I think there are tweaks I would make to the look – starting with these boots.

For balance with the skirt’s short hemline I can see the idea behind opting for a thigh high height. But I’m not a fan of the foot bed shape, kitten heel, and slouchy combination of these particular Stella boots.

Had it been my choice, I would have preferred her trusty knee high ‘Babel’ Louboutin boots for a similar but more streamlined shoe.

Worn with: Jacquie Aiche necklace + bracelet, Jacquie Aiche + Foundrae earrings, Mazin Jewels rings, Stella McCartney bag, and Miu Miu skirt

Photo by Getty

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

Sézane ‘Jessie Brown Python Print Loafers’ – $265.00

The heeled loafer/oxford is a long beloved style in Taylor’s wardrobe. Down the line, I can totally see her rewearing this pair with a pleated mini skirt or dress.

There’s also something about wearing a python print the week after your latest re-record release that is not particularly subtle.

Worn with: Gant sweater, Mansur Gavriel bag, and The Row pants

Photo by Gotham ℅ 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 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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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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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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Out and about | New York City, NY | October 14, 2023

Greymer Spring/Summer 2014 sandals – no longer available

If you have ever thought: Surely Taylor doesn’t always consider what she wears and the messaging behind it. This post is for you.

Now defunct, Greymer is an Italian brand established in 1980. More importantly, the shoes Taylor is wearing here are from their Spring/Summer 2014 collection. When the entirety of the fashion world is at your disposal, why wear a pair of shoes from nearly a decade ago that so happens to nod to the year your upcoming re-record was originally released in?

Fashion history aside, I loved how the metallic heel of these sandals continued the gold hardware present through the rest of the outfit (necklace, corset straps, bag).

Worn with: Maria Tash earrings, Gant coat, Mazin Jewels necklace, Versace corset, and Aupen bag

Get the look: Michael Kors, $155.00

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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