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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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Out and about | New York City, NY | September 11, 2023

Jacquie Aiche ‘Large Pave Teardrop Cap’ – $24,400.00
Jacquie Aiche ‘Marquise Center Flying Thunderbird Drop Stud’ – $4,550.00
Foundrae ‘Sister Hook Choker’ – $6,365.00
Foundrae ‘Diamond Center Heart Medallion’ – $1,095.00
Alaïa ‘Fluid Mini Dress’ – $2,914.00
Mansur Gavriel ‘Cloud Clutch’ – $745.00
Jacquie Aiche ‘Evil Eye Bracelet’ – $5,250.00
Prada ‘Suede Block Heel Sandal’ – no longer available

Taylor was spotted out with friends including Gigi Hadid, Cara Delevingne, Blake Lively + Reynolds, and Zoe Kravitz + Channing Tatum.

Pale blue is a reliably lovely colour on Taylor (and really brings out her eyes). Plus, she’s used it to very fun effect as seen on the last night of the Los Angeles string of Eras Tour dates to support the announcement of 1989 (Taylor’s Version). Which is a very interesting thing to bring up as in this case on the shoe front, she went tonal in a matching pale blue pair of heels that veer more ‘sweet’ than ‘city strut’ like the stilettos we’ve seen her rock in the past – such as the 6” towering heels we would have seen her wear in the original 1989 era back in 2014.

A very fun juxtaposition to think about in terms of a visual comparison.

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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

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Out and about | September 5, 2023

Yuzefi ‘Fortune Cookie Bag’ – $593.00

There are a few things that are mainstays of Taylor’s fashion that makes her sense of style not only unique to her, but noteworthy for a celebrity of her stature.

Her penchant for repeating/rewearing items (often over the span of many years), her love of an accessible brand (think Urban Outfitters, Free People), and her intentionality in opting for lesser known or indie brands. We see that third point on display here in opting for a bag by Yuzefi — a London-based brand by Iranian-born Naza Yousefi who started her namesake-inspired accessories line in only 2016.

There’s also a part of me that wonders if the positive manifestation and future-forward thinking of the style name appealed to her.

Worn with: Ralph Lauren hat, Gabriela Hearst top, Vince pants, and The Row boots

Photo by Robert Kamau via Getty Images

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Out and about | September 5, 2023

Gabriela Hearst ‘Nevin Cashmere and Silk Tank Top’ – $490.00

As mentioned, this silk cashmere top acts as yet another textural fabric moment in this ‘fit that makes each piece pop against each other, even when existing in a relatively monochrome palette. The pointelle knit here keeps things a little more breathable, even when a pair of pants (albeit breezy ones made from linen) and heavy leather boots dominate the outfit.

Worn with: Ralph Lauren hat, Yuzefi bag, Vince pants, and The Row boots

Photo by Robert Kamau via Getty Images

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Out and about | September 5, 2023

Ralph Lauren ‘Corduroy Cap’ – $69.50

I’m kind of into the way the ribbing on the corduroy of this cap interplays with the textured ribbing of her tank top. Plus how the dark logo pops off the brown field of the cap to tie into the rest of the colour palette of this ‘fit.

Worn with: Gabriela Hearst top, Yuzefi bag, Vince pants, and The Row boots

Get the look: Old Navy, $19.99

Photo by Robert Kamau via Getty Images

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Out and about | September 5, 2023

The Row ‘Robin Boots’ – $1,290.00 $774.00 (on sale)

Taylor opted to rewear her pair of chunky The Row boots while out and about today. They do offer a grounded, heavier base to counterbalance the lightness of her tank top. Plus some height to prevent hem puddling of her cargo pants. I would have been tempted to opt for some Converse sneakers, but Taylor often goes unique in her shoe styling – such is her calling card.

Worn with: Ralph Lauren hat, Gabriela Hearst top, Yuzefi bag, and Vince pants

Photo by Robert Kamau via Getty Images