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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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At Arrowhead Stadium | Kansas City, MO | October 12, 2023

Prada ‘Black Lace Up 110 Military Boots’ – $1,205.00

Despite not having HQ images of Taylor’s full ensemble (which I’d love!), I still feel reasonably confident on these boots which I suspect are an older pair by Prada that Taylor previously wore in September 2019 while on stage during her City of Lover concert.

Worn with: WEAR by Erin Andrews jacket and Balenciaga corset

Also worn: City of Lover concert

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Out and about | New York City, NY | September 11, 2023

Jacquie Aiche ‘Large Pave Teardrop Cap’ – $24,400.00
Jacquie Aiche ‘Marquise Center Flying Thunderbird Drop Stud’ – $4,550.00
Foundrae ‘Sister Hook Choker’ – $6,365.00
Foundrae ‘Diamond Center Heart Medallion’ – $1,095.00
Alaïa ‘Fluid Mini Dress’ – $2,914.00
Mansur Gavriel ‘Cloud Clutch’ – $745.00
Jacquie Aiche ‘Evil Eye Bracelet’ – $5,250.00
Prada ‘Suede Block Heel Sandal’ – no longer available

Taylor was spotted out with friends including Gigi Hadid, Cara Delevingne, Blake Lively + Reynolds, and Zoe Kravitz + Channing Tatum.

Pale blue is a reliably lovely colour on Taylor (and really brings out her eyes). Plus, she’s used it to very fun effect as seen on the last night of the Los Angeles string of Eras Tour dates to support the announcement of 1989 (Taylor’s Version). Which is a very interesting thing to bring up as in this case on the shoe front, she went tonal in a matching pale blue pair of heels that veer more ‘sweet’ than ‘city strut’ like the stilettos we’ve seen her rock in the past – such as the 6” towering heels we would have seen her wear in the original 1989 era back in 2014.

A very fun juxtaposition to think about in terms of a visual comparison.

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Attending the premiere of The Banshees Of Inisherin | New York City, NY | October 10, 2022

Prada ‘Chocolate Flow Block Heel Loafers’ – $1,250.00

Taylor has long loved a pair of heeled loafers or oxfords. In past years, she may have paired them with tights and a cute dress in the fall. Nowadays, her new admiration for blazers and trousers feels more up my alley, sartorially. And I’m obsessed with that growth.

Worn with: Etro bag

Get the look: Steve Madden, $99.00

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2022 Tribeca Film Festival | New York City, NY | June 11, 2022

Prada ‘Patent Leather Loafer Pumps’ – no longer available

As mentioned, I do appreciate the pop of red via the shoes here, especially in coordination with her signature red lip. They also feel like a ‘fun’ and fashun take on a typical business pump which I’m sure was the intent. My preference would have been a sleeker heel but I appreciate that Taylor is a longtime lover of an oxford/loafer pump.

What makes these shoes particularly interesting is they are from Prada’s Fall 2010 collection.

Worn with: Max Mara suit, Vrai earrings and rings, and Ettika bracelets

Get the look: ASOS, $39.25

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21 days til November 12 (x) | October 22, 2021

Stuart Weitzman ‘Wylie Signature Leather Loafer’ – $395.00
Prada ‘Scallop Pointy Toe Pump’ – $750.00
Keds ‘Taylor Swift Velvet Glitter Limited Edition’ – $39.95 (sold out)
Manolo Blahnik ‘Maysli Slingback Pump’ – $1,606.00

Thanks to an Anon for pointing out Taylor’s former limited edition collaboration with Keds that was released during the original run of RED (2012). Swapped in with some black laces!