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

Stella McCartney ‘Frayme Crocodile Effect Bucket Bag’ – $1,995.00

Taylor has carried many chain Stella McCartney designs over the years in the forms of various sized bags and even backpacks, namely from Stella’s ‘Falabella’ line – it’s an iconic signature of Stella. I like that the hardware ties in to the jewelry of the ‘fit and the colour continuing the theme of black.

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

Photo by Getty

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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 | 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

Mansur Gavriel ’M Frame Box Bag’ – $895.00

In terms of recycling accessories, Taylor previously carried this bag back in May. Back then, she paired it with a fresh white eyelet set by Ralph Lauren and complementary minimalist brown sandals by Aeyde. It’s fun here to see her carry this bag again in a new season and see it work just as well with the fall-like palette of her outfit today.

Speaking of things we’ve seen before – if I had to guess, Taylor’s security guard in the background here is also carrying her very first Gant piece we saw last month – their cropped wool blazer jacket.

Worn with: Gant sweater, The Row pants, and Sézane loafers

Also worn: May 24, 2023

Get the look: Matt & Nat, $110.00

Photo by Gotham ℅ 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 | November 3, 2023

Gant ‘G Pattern Collar Sweater’ – $200.00 $87.00

Perhaps it’s the combination of the colour palette of this collared sweater paired with wide leg pants but this feels like a throwback to the 70s energy first established in the early days of promotion during the Midnights era. There’s something modern Daisy Jones about it.

I think a pair of wide leg pants a bit more fitted through the waist and hip would have created a more balanced shape for the entire ‘fit. But I do appreciate the autumnal tonal vibes consistent throughout the ensemble.

In terms of creating a consistent fashion story, Taylor’s last two times wearing Gant were as part of significant outings with Travis (the SNL after party #hardlaunch and Chiefs v Jets game). Worth mentioning as we head into yet another KC Chiefs game weekend.

Worn with: Mansur Gavriel bag, The Row pants, and Sézane loafers

Photo by Gotham ℅ Getty

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Out and about | New York City, NY | October 27, 2023

Hunting Season ‘The Trunk in Satin w/ Tassels’ – $925.00

All of Taylor’s fashion hallmarks were on display here with this outfit: 1) An enviable high/low mix by pairing high street like Madewell with designer like Gianvito Rossi 2) Repeating pieces like her Acne Studios corduroy skirt, last seen October 2022 3) Supporting smaller, indie designers like NY-based brand Hunting Season. Which also, in my opinion, has a not-too-farfetched reference to “I Know Places”.

Worn with: Madewell blazer, Jacquie Aiche earrings + Foundrae necklace charm, Mazin Jewelry necklace + Foundrae chain, Acne Studios skirt, and Gianvito Rossi boots

Photo by Getty