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Chiefs vs Patriots | Foxborough, MA | December 17, 2023

Rails custom skirt – not available for purchase

Taylor has been a longtime fan of a plaid mini skirt but it’s also an item that has had a resurgence in her wardrobe these last few months. Skirt-wearing Taylor has two modes: chic and polished with a tucked in top/bodysuit and tall heeled boots or cozily retro with an oversized sweater or sweatshirt and flat shoes. In this case, it’s fun to see when a brand picks up on that love and creates a custom piece to reflect her style with that in mind.

Known best for their plaid shirts, Rails is a brand that Taylor is deeply familiar with – having worn them as early as 2012. Rails VP Linney Warren described Taylor to People as “the ultimate muse for this season’s schoolgirl trend.” Adding, “When we were imagining custom pieces to create for her, we wanted to give her things that she could seamlessly incorporate into her wardrobe — we were thrilled when she chose to style it back to a vintage sweatshirt for the Chiefs game for a bit of nostalgia!”

Given that Taylor’s skirt is custom, it isn’t available for purchase but the Prim skirt is the closest match currently retailing.

Worn with: Vintage sweatshirtKut the Knit beanie, and Mejuri ring

Photo by Kathryn Riley via Getty Images

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Out and about | New York City, NY | December 8, 2023

Gant ‘Shearling Jacket’ – $1,700.00
Guest in Residence ‘Waffle Polo in Hunter’ – $445
.00 (sold out)
Miu Miu ‘Pleated Check Mini Skirt’ – sold out
Calzedonia ‘Sheer 40 Denier Tights’ – $10.00 $5.00 (on sale) [Thanks Anon!]
Saint Laurent ‘Le 5 à 7 Hobo Bag’ – $2,650.00
Reformation ‘River Boot’ – $478.00

Taylor’s love of Gant’s outerwear continues – this time in an oversized shearling jacket that’s a spin on a classic aviator style and feels very cozy wintery and stands as a nice proportional contrast to her (repeat) Miu Miu skirt we previously saw her wear while on a date with Travis in Argentina when one of her shows was rained out and postponed. Taylor also owns this particular mini in another plaid check print.

One thing that I feel like Taylor does often is create interesting, unexpected, colour palettes with her outfits. It’s something she’s done for a long time that feels very classically ‘her’. If it were me, I would have done a sandwich style moment and opted either for the same camel tone as her Saint Laurent bag in both her carry item and boots or perhaps even both a dark chocolate brown to tie into the piping on her Gant jacket. As-is, her ‘ruby’ Reformation boots create a colour (albeit Christmas-y) contrast.

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Out and about | New York City, NY | December 5, 2023

Stella McCartney ‘Frayed Checked Wool Blend Tweed Mini Skirt’ – $975.00

Just the other day in stories I was talking about the history of Taylor and mini skirts and how – especially as we approach the end of 2023 – that this year has seen quite a revival for them in her candid fashion.

While it’s fun to see Taylor’s style come to fruition in the moment, I very much think that consideration for an ‘era’ as a whole can really only be done in hindsight once we have a birds eye view of the time period in order to be able to really pull out trends, commonalities, and patterns.

In this current moment, a wool tweed mini (esp paired with designed tights – another closet staple Taylor has a long history with) feels preppy, smart, and wintery. Almost Gossip Girl-esque!

Worn with: Stella McCartney coat, VRAI + Jacquie Aiche + Louis Vuitton jewelry, Sheertex tights, Jimmy Choo x Jean Paul Gaultier heels

Photo by James Devaney via Getty

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At Lambeau Field | Green Bay, WI | December 3, 2023

Louis Vuitton ‘Strap Detail Mini Wrap Skirt’ – $3,400.00

As we approach the end of the year and I start to turn my gaze backwards on 2023’s fashion to pull together my annual list of Favourite Outfits, in addition to really thinking about what ‘fits to include on my last of faves I also like to think about trending items and patterns that crop up.

All this to say that I feel like in looking back on this year, one such trend might just be the mini skirt. Taylor has worn many over the course of her career, but she’s really been rocking many this fall at least – especially paired with tall boots.

Worn with: VRAI earrings, Cartier necklace, Stella McCartney coat, and Stuart Weitzman boots

Photo by Mark Hoffman for the Milwaukee Journal Sentinel

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Out and about | Buenos Aires, Argentina | November 10, 2023

Miu Miu ‘Pleated Check Mini Skirt’ – sold out

I am an ardent supporter of formula outfits and have definitely worn a combination of this ‘fit myself. I think this iteration with flat chunky boots with a shorter shaft height are a more balanced (and trendy) iteration of the black sandwich style + plaid mini skirt outfit than the last time we saw this combo on her.

If this particular skirt looks familiar to you it’s because Taylor liked it and so she got it in a different colour after wearing this in a plaid iteration just last week – another closet approach I am personally guilty of.

Worn with: Prada bag and The Row boots

Get the look: Urban Outfitters, $65.00

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

Miu Miu ‘Brown Plaid Skirt’ – $1,489.00

By item, this plaid pleated skirt is nothing new for Taylor’s style which has for years loved a “schoolgirl”-esque mini. By silhouette, however, the way this skirt hangs is more low waist then Taylor would normally opt for.

The effect feels very Rachel Green meets Regina George.

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

Get the look: H&M, $24.99

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 15, 2023

Khaite ‘Keene Leather Mini Skirt’ – $2,100.00

It isn’t often that a leather skirt makes one giggle, but this one did because Taylor exhibited an age old habit of wearing things backwards. Here, she chose to wear the exposed zipper of the skirt to the back, to emphasize the unique side seaming detail at the front.

The joy of adding yet another item to the TSS Backwards tag.

Worn with: Maria Tash earrings, Alessandra Camilla Milano earrings, Jean Paul Gaultier top, Balenciaga corset, Roger Vivier bag, and Louis Vuitton boots

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Out and about | New York City, NY | September 8, 2023

Foundrae ‘Sister Hook Choker’ – $6,365.00
Foundrae ‘Forever & Always A Pair Oval Pendant’ – $1,450.00
Sandy Liang ‘Paris Skort’ – $625.00
Louis Vuitton ‘Camera Box Bag’ – $3,450.00
Gucci ‘Half Horsebit Almond Toe Boots’ – $905.42

One thing I love about this outfit is the tension of shapes and textures. The soft, angular swoop of her asymmetric top, knife pleats of her skort, and the sharp boxy lines of her LV camera bag all create certain, strong lines. These all work in direct contrast to the mussed, textured curls we see here that prevent it all from being too put together and polished.

I’m not one to look a gift skort in the mouth, so I won’t be reading into the “Paris” Easter Egg of it all. Especially one as chic as this. Any outfit defined by some sharp pleats and black is perfect in my books.

Let us instead admire how the confidence of an inner pair of shorts has given us all the gift of Taylor’s killer legs thanks to short hemlines.

If I had to, and could, copy and paste an outfit in its entirety on my body from recent Taylor history – it would be this one. At my core, I’m a girl who loves neutrals and polish served with a side of edge. And you all know I’m a proponent of the sandwich style (that is, to match two elements of an outfit between a contrasting colour).

Just add a blazer and we’re golden.

Get the look: Emory Park skort, $56.00 and Gap boots, $134.00