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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

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Out and about | New York City, NY | September 18, 2023

Vince ‘Houndstooth Wool Blend Coat’ – $845.00
Cartier ‘Agrafe Herringbone Twisted Necklace’ – $27,250.00
Versace ‘Greca Goddess Medium Leather Top-Handle Bag’ – $2,650.00
Christian Louboutin ‘Pumppie Botta Leather Knee-High Boots’ – $1,795.00

Watching people excel in their given field is always a pleasure and a joy to watch. It’s how I feel seeing Taylor dancing with abandon at awards shows or singing to sold out stadiums of 70,000 people. But it’s also how I feel when I see her step out in fall attire in NYC. What a thrill! She’s always had a special knack for layers and colour palettes, but Taylor really does kill fall dressing. So much so that this latest string of outfits has been a consistent, “Yes I will copy + paste that onto my body” response from me. I’m just a sucker for a good piece of outerwear and an outfit dominated by black.

Speaking of black, two notes on her black accessories here.

Choice of brand is always something that comes to my mind, even when we see Taylor out and about in her daily life. Seeing her wear Versace immediately brings to my mind not only the recent memories of her outing at the MTV VMAs just last week (in classic black and gold Versace) but also me of Versace’s top tier placement in the Eras Tour setlist as part of her opening set. It’s subtle, of course, but I can see how even that simple evocation over into her street style would be a great way to keep top of mind her huge award show sweep and that she’ll be back on her record-breaking global stadium tour in less than two months. The bag itself has such a dreamy shape – love the curves.

The boots, on the other hand, immediately had me do a double take because they are incredibly similar to the ‘Babel’ Louboutins she would wear so often in her early years. Given Taylor’s propensity lately for going back into her clothing archives, that really would have given me a shock. But no, this pair differs by a slightly different heel and a side zip.

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Out to dinner w/ Blake Lively | New York City, NY | September 16, 2023

Tod’s ‘Leather Crossbody Mini Bag’ – $1,825.00
Foundrae ‘Petite Chubby Ear Hoop’ – $1,570.00
& Other Stories ‘Leather Knee Boots’ – £145.00 (no longer available)

Taylor continues her social streak in NYC, heading out to dinner with Blake Lively at a members only club wearing a neutrals-dominated outfit (my favourite kind). A few people asked me how I felt about the combination of a cropped black cardigan, slate grey mini skirt, and burgundy boots. To which I say: Yes. This is definitely an outfit I’d personally wear.

But what’s so fun about it is that the idea of a pleated skirt and boot combination is not new to Taylor’s style. She’s been wearing some iteration of this pairing ever since she was a teen. What’s fun to watch is how she makes slight styling adjustments to make it more current and also more ‘her’ of today. It’s that blend of familiarity but modernity that I feel is so relatable to Taylor’s style and what makes her feel so approachable and real, but also recognizable for those who have been observing her ‘fits change from era to era. She’s always there underneath at all!

That aside, these particular boots actually have a story within Taylor’s fashion history. They first debuted in November 2014 and haven’t been seen since winter 2015. With 1989 (TV) around the corner, this obviously has my brows raised. If intentional, what a throwback.

The Tod’s bag is one she also wore earlier this year with a vintage NYU sweater.

On the jewelry front, this particular style from Foundrae (a brand she’s been loving as of late in her pursuit of the perfect stack) does come in a cute initial version which would be very up Taylor’s alley (she loves initial jewelry). However, given that she owns and has worn the matching necklace of the pictured style, this is the one I’m going with for now.

To see all the times Taylor has worn these boots, click here.

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MTV Video Music Awards after party | September 12, 2023

Alessandra Camilla Milano ‘Blue Rain Diamond Cuffs Drop’ – $2,490.00
Mindi Mond ‘Bullet Shaped Hexagon Platinum Diamond Ring’ – $10,500.00
Natasha Schweitzer ‘Double Band Pear Diamond Ring’ – $3,367.00
Nicole Rose ‘Diamond Cross Over Ring’ – $1,150.00

Worn with: Vintage necklace, EB Denim dress, Aquazzura bag, and Aquazzura sandals

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MTV Video Music Awards after party | September 12, 2023

Aquazzura ‘Sundance Crystal Embellished Sandals’ – $2,174.00

The platform here adds to the ‘cheek’ of the look and balances out that short hemline.

Worn with: Vintage necklace, Alessandra Camilla Milano + Mindi Mond + Natasha Schweitzer + Nicole Rose jewelry, EB Denim dress, and Aquazzura bag

Get the look: Steve Madden, $149.95

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MTV Video Music Awards after party | September 12, 2023

EB Denim ‘Polka Dress’ – $480.00 $336.00

What an incredibly fun after party dress. It’s sassy, very short, and feels like another 90s throwback (who else remembers all the ultra #FASHUN denim styles that hit the red carpet then?). In some ways, I can actually see how this could have theoretically worked at the award show itself, with some tweaks. 

The addition of the red lip here does a great job signaling “party!” but I do wonder what a sleek ponytail would have done for the look.

Worn with: Vintage necklace, Alessandra Camilla Milano + Mindi Mond + Natasha Schweitzer + Nicole Rose jewelry, Aquazzura bag, and Aquazzura sandals