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#ForAFortnightChallenge | April 25, 2024

Popflex ‘Crisscross Hourglass Booty Short’ - $45.00


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#ForAFortnight Challenge | April 19, 2024

Venroy ‘Stripe Boxer Short’ - $150.00 (no longer available)

Worn with: Zimmermann top

Also worn: With Blake Lively September 2022


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The Tortured Poets Department | April 19, 2024

Saint Laurent ‘Silk Tank Top’ - $650.00
The Row ‘Ausra Brief’ - $790.00

Our first look at a new era. 

With so little to go off of, there’s still much to parse here. Between the bedsheets, the pose, and (of course) the clothes - a pair of briefs and a slinky tank falling off the shoulder - to me evokes a combination of both intimacy and guardedness. Soft and vulnerable, but a little careworn and protective. This is the balancing act I think Taylor’s been playing with her whole life (an open heart revealed through deliberate acts) but feels painted in a more (pun intended) black and white way on this album cover. Even the sheerness of the top that plays with transparency, but only how much she permits, strikes me. 

And, it turns out, Taylor wearing The Row (and toting a few new YSL bags too) so much over the last few months was no coincidence (is there ever one with Taylor, really?). Her cozy selects appear to be (as confirmed by her stylist) to be this sheer tank and ribbed brief by YSL and The Row. 

While there’s so much about this album’s themes and sound that we don’t know - it’s of course fun to guess! The idea of the tortured artist to me sounds like it has the opportunity to explore the self-loathing andthe satire Taylor has previously toyed with on both “Anti-Hero” and “Blank Space”. Both the sincere truth of self-analyzing a life of being a tortured poet herself while also poking fun at the muses in her life who have aped at being tortured poets - perhaps delivered with a tongue firmly in cheek accompanied by a smirk and an eyeroll. 

I’m excited to see what awaits us and learn more about this project as well as your Critically Kind thoughts. 

Editorial Note: Original cover image captured by Beth Garrabrant - Taylor’s album photographer since folklore. In place of Beth’s image, for which she retains rights, I’ve commissioned a lovely demonstrative illustration by the talented Amelia Noyes.


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At MetLife Stadium | East Rutherford, NJ | October 1, 2023

Area ‘Logo Lettering Denim Shorts’ - $528.00

Another very fun (and slightly more spicy) outfit I’d copy + paste from Taylor.

Going back in fashion history, some of you may recall back in November 2021 when Taylor was a musical guest on #SaturdayNightLive that she wore a pair of crystal embellished plaid pants by Area that I said was a travesty we never got to see in full from the back due to the very fun crystal-trimmed slits that are signature of the brand. It’s very fun to see the logo lettering of ‘AREA’ spelled out here and visible thanks to the black bodysuit she layered underneath.

More recently, some of you may remember this brand as the one behind Taylor’s butterfly jeans - the ones she wore for those very first New York candids back in April 2023.

Worn with: Gant jacket, Logan Hollowell necklace, and Christian Louboutin boots


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At Arrowhead Stadium | Kansas City, MO | September 24, 2023

Ksubi ‘Roll'n Out Distressed Denim Shorts’ - $190.00 (no longer available)

Blast from the past! Taylor first acquired these shorts back in 2018 and wore them for a few reputation Tour meet and greet opportunities.

Worn with: Ralph Lauren hat, New Era jacket, Jacquie Aiche earring, Dôen top, Louis Vuitton bag, and New Balance sneakers

Get the look: Superdown, $24.18


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Out and about | New York City, NY | May 22, 2023

R13 ‘Crossover Denim Shorts’ - $365.00

With Eras Tour shows in MetLife scheduled for this weekend, I had anticipated seeing Taylor out and about in the city. The only question was - how soon would that be off the heels of her Gillette dates?

The answer was right away.

Worn with: R13 shirt, Ralph Lauren bag, and A. Emery sandals

Get the look: AE, $49.95

Photo by Gotham ℅ Getty


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With Blake Lively (x) | Watch Hill, RI | September 17, 2022

Venroy ‘Oversized Woven Stripe Shirt’ - $170.00
Venroy 'Stripe Boxer Short’ - $150.00

It warms my heart so much every time we see displays of this friendship. Blake took to Instagram the other day to post intimate photos of her over the course of her latest pregnancy - one including a pic with Tay presumably over the last few months at her Rhode Island home where she wore the most breezy looking matching striped set.

Worn with: Ray Ban sunglasses


Recording “You All Over Me” (From The Vault) (x) | March 25, 2021

Alexander Wang ‘Grid Poplin Tie-Waist Skort’ - $550.00 (sold out)

Based on the fact that Taylor has worn this precise style in another colourway, I’m willing to bet this is the same style. 

Worn with: Rails top


Keds ads | Spring 2014

Elizabeth & James ‘Addeline Jacquard Linen Shorts’ - no longer available

Worn with: Anthropologie blouse and Keds sneakers


We Can Survive Concert | October 19, 2019

Stella McCartney ‘Faux Leather Shorts’ - $1,100.00 $660.00


TMall Double 11 Gala | Shanghai, China | November 11, 2019

Joseph Cassell custom

Oh how much do I genuinely love this. The boots are a serve, the holographic print with very subtle rhinestoning is pleasing to the camera and the lights but isn’t a complete 100% sparkle look. I also like the tie belt and slightly oversized shirtdress look paired with the slight slouch of the boots. It feels very *swagger* to me. 

Worn with: Graziela Gems + Rachel Katz rings


City Of Lover concert | Paris, France | September 9, 2019

Faith Connexion custom shorts

For those of you who followed reputation fashion, this brand (and silhouette) may look incredibly familiar to you. Taylor fairly obsessively wore Faith Connexion over the course of the reputation era and donned a fair amount of their signature tie-front shorts. 

As seen in army green, camo, dress version, red plaid. 

Worn with: Versace bodysuit, Implicite bra, and Prada boots


BBC Radio 1 Live Lounge | September 2, 2019

Saint Laurent ‘Embellished Leather Shorts’ - $2,490.00

Taylor delivered one of her best Live Lounge performances to date with a six song set. I loved every last choice. 

Worn with: Saint Laurent blouse, Versace belt, and Saint Laurent boots

Also worn: “Lover” music video

Get the look: Express, $39.99


Lover album photoshoot | August 23, 2019

One Teaspoon ‘Bandit Shorts in Moonstone’ - $102.00

Every single outfit in this photoshoot is so beyond dreamy. 

Worn with: Taylor Swift top and Dr. Martens booties

Get the look: Forever 21, $13.93


Performing “You Need To Calm Down” + “Lover” | August 26, 2019

Versace custom ensemble


To continue the theme of all things Versace, her performance ensemble was also a custom piece by the Italian fashion house. The purple and gold combination screams Wonder Woman meets royalty, no?

Worn with: Kallati earrings + Brumani + Misahara rings, Versace necklaces, Versace bracelets, and Christian Louboutin boots


THEME