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

The Row ‘Clotho Blazer’ – $3,350.00

Later in the evening, Taylor donned a boxy, oversized blazer that effectively created a ‘new’ silhouette for the outfit that I think I much preferred to the look sans blazer.

Possibly because it eliminated the appearance of the low rise skirt – or simply because I just love a blazer moment.

Photo by Getty

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

Madewell ‘Larsen Blazer in Leather’ – $548.00

This is a great example of Taylor dressing to formula. While we haven’t seen her in this exact combination before, to me it struck a similar note to her KC Chiefs vs NY Jets game ensemble which also comprised of a few, key similar components: Statement leather topper, simple black top, contrasting short bottoms, complementary leather boots.

While that outfit felt like a hot summer evening outfit, the colour palette here firmly establishes it into ‘fall’ territory.

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

Photo by Getty

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Out and about | New York City, NY | October 26, 2023

Ralph Lauren ‘Corduroy Collar Cotton Field Jacket’ – $762.00

If I were to have picked a piece of outerwear by any brand to complement the equestrian energy of this ‘fit, it would have been Ralph Lauren – so I’m delighted that this toffee coloured field jacket is a Polo by RL piece.

I’ll also say that while previously the two tone mix of browns sans coats wasn’t entirely sold on me that now with the addition of a third brown shade that the mixture now feels more ‘complete’ and robust – like a true, intentional fall-leaning palette.

Worn with: Stella McCartney shirt, Tod’s bag, and Prada boots

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Attending SNL after party | New York City, NY | October 14, 2023

Gant ‘Houndstooth Wool Trench’ – $825.00

How does one dress for a hard launch? For an outing that all parties involved would know would garner headlines, it’s a lot to ask of an outfit.

Stepping out in NYC to make a surprise appearance on SNL in support of Ice Spice, Taylor attended the show’s after parties with Travis Kelce.

Her outfit of choice falls in line as of late with her tendency for luxe neutrals and suiting. This particular choice of outerwear is her third time in recent weeks to opt for Gant – the most recent being her MetLife outfit at the Chiefs v Jets game courtesy of a leather shirt jacket.

Gant is a brand steeped in the American collegiate prep fashion and, since the 70s and changing trends post-war, has had quality clothes informed by athletics and comfort at its core. According to the brand, “As sports activities influenced many creative tailoring features, the demand for a comfortable look continued to spread. GANT shirts helped define the casual-yet-smart look”. What better brand to turn to that nods to both Americana and athleisure to kick off the official public start to a relationship with an NFL player.

The added level of intrigue is Taylor’s choice of outerwear here is from the brand’s menswear line. Pairing it with ultra feminine pieces (a bustier, heels) and wearing it casually one shoulder feels simultaneously powerful yet effortless.

The jacket around her shoulders? Hers.
And in case you forgot, she is The Man.

What a message.

Worn with: Maria Tash earrings, Mazin Jewels necklace, Versace corset, Aupen bag, and Greymer sandals

Get the look: Steve Madden, $176.47

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

WEAR by Erin Andrews ‘Kansas City Chiefs Windbreaker’ – $112.99

It wasn’t really a matter of ‘if’ but ‘when’ Taylor would opt for a piece of football attire by Erin Andrews. Known most for being a prominent NFL sideline reporter, Erin launched her ‘WEAR’ womenswear apparel line in 2019 to give a variety of wearable options for women. Born out of necessity and what Erin perceived as a major gap in the market. “There was … not a lot of options for female fans,” she told Insider of her launch.

A natural choice for Taylor to wear as she opts for home team sportsball merch.

Worn with: Balenciaga corset and Prada boots

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Out and about | New York City, NY | October 1, 2023

Gant ‘240 Mulberry Street Relaxed Leather Shirt’ – coming soon (pictured similar)

I’ve mentioned before being a fan of what I call ‘sandwich’ styling – which is to have two similar elements in an outfit bookend a contrasting element. To sandwich is to imbue an outfit with balance. In this case, the blue of her crystallized denim shorts is anchored by a lot of black accessories. Including this edgy leather shirt by #Gant from their upcoming exclusive FW 2023 collection dubbed ‘240 Mulberry Street’ – named after the address of their creative headquarters in NYC.

The impact of this in the context of sandwich styling also works in multiple regards. Proportionally, the longer length of both the jacket and her Louboutin boots (also leather, upping the sandwichification of the ‘fit) offsets the short hem of her shorts. In short – I loved this styling.

You may recall that last week Taylor actually popped into the very same Gant NYC store to purchase a coat on a whim while out with friends. I’d hazard a guess the team was so delighted they sent through this coat as thanks.

Worn with: Logan Hollowell necklace, Area shorts, and Christian Louboutin boots

Get the look: ASOS, $79.99 / Abercrombie, $90.00

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

New Era ‘Womens Full Zip Windbreaker’ – in store only

For reasons unknown Taylor took a jaunt to Kansas City to take in a sporting event. Taylor is familiar with this stadium having just been there in July during the Eras Tour.

New Era happens to be the main sponsor for NFL merchandise, but I’m sure the name appealed to Taylor regardless.

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

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Out and about | New York City, NY | September 21, 2023

Gant ‘Cropped Wool Blazer Jacket’ – $475.00

To keep things relatively tonal, Taylor shrugged on a cropped blazer jacket to coordinate with her trousers.

Worn with: Logan Hollowell necklaceBrandon Blackwood bagAlaïa bodysuit, The Row belt, The Row pants, and Aquazzura sandals

Get the look: Madewell, $129.99

Photo by Getty

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Out to dinner with Sophie Turner | New York City, NY | September 19, 2023

EB Denim ‘Webster Trench’ – $480.00

I recently commented how Taylor’s street style is no less thought of and considered than her red carpet fashion. The other day, I noted that Taylor’s choice to accessorize via a black and gold Versace bag drew a subtle mind connection both to the recent MTV VMAs (where she wore a black and gold Versace gown) as well as to Versace as an Eras Tour costume provider (and that she’ll be back on tour shortly).

Here, that train of thought is ever more present courtesy of this dramatic denim trench. Fashion-wise it provides a dramatic proportional moment to her boots and short sweater dress that makes it a real trendy (and throwback 90s/00s) piece, but it also flips right back to the MTV VMAs and bookmarks that night neatly as this is the same brand she wore to the after party following that Versace moment.

Worn with: Mckenzie Liataud necklace, Luana Italy bag, Reformation dress, and Reformation boots

Photo by Pap Culture