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MTV Video Music Awards | September 12, 2023

Anita Ko ‘Stacked Diamond Ear Cuff’ – $5,297.00
Maria Tash ‘Floating Diamond Tassel Hoop’ – $25,300.00
Van Cleef & Arpels ‘Onyx and Diamond Ring’ – $12,000.00
David Webb ‘Diamond Ring’ – quote available upon request to designer
Ita Jewelry ‘Eterno Pavé Ring’ – $1,480.00
Joseph Saidian & Sons vintage diamond necklace’ – $65,000.00
Anita Ko ‘Triangle Eternity Choker’ – $43,574.00

Over the last few candid appearances, we’ve seen Taylor experimenting more with the fine art of a necklace stack and I can’t help but playfully wonder if it was in part a lead up (or inspired by) the layered styling for her MTV VMAs appearance.

The ‘more is more’ approach to accessorizing here is fun to observe, as Taylor doesn’t typically pile it on this excessively for red carpets. But it does up the ‘messy glam’ factor of her gown and mussed, spilling out updo.

Worn with: Versace gown, Foundrae + Jacquie Aiche + vintage bracelets, and Jimmy Choo sandals

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MTV Video Music Awards | September 12, 2023

Versace custom gown (pictured similar)

As is her way, Taylor can only be consistently expected to do one thing: subvert expectations. Swiftly (some might say) bypassing an opportunity to plug any of the three albums she’s either released, or is on the precipice of releasing, she went straight to a very reputation-coded Versace gown. The likes of famed supermodel lore or legendary Liz Hurley status. It’s sexy, it’s slinky, it’s very distinctively signature Versace – using Medusa-embossed buttons in a pseudo snap closure style instead of the more overt safety pin (this detail continues on the strappy open criss-cross back all the way down the back to the end of her train, which is worth a look on its own).

I personally love a classic Versace look such as these. They’ve been done, and done a lot. But I can’t fight a classic sexy siren gown like this. The decision to forego Taylor’s signature red lip, I think, is a smart one that prevents the look from going too overboard. In my opinion, the styling choices were either pile on the jewels or pile on the crimson lip. And Taylor/her team went for the former – something that’s atypical of her style. The mussed hair with the trailing pieces left out of their updo feel “roll out of bed” intimate and sensual and feels akin to the curly bangs from the reputation photoshoot. But I can’t help but think an uber sleek blowout could have been great here. 

If indeed a nod to reputation, I’ve always seen that album as one of two diametrically opposed forces: the external perceptions of who you are vs the internal realizations of the life you’re quietly building. To use a dress with so many asymmetrical details (the bodice, the straps, and even in the movement of the button detailing literally splicing her in half) as an embodiment of that would be quite appropriate. It’s also a smart use of a brand’s signature design details to (possibly) use for your own means.

Not to mention this is precisely the kind of dress at least I would envision buying so someone else could take it off. 

Worn with: Anita Ko + Maria Tash + VCA + David Webb + Ita + vintage jewelry, Foundrae + Jacquie Aiche + vintage bracelets, and Jimmy Choo sandals

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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

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Out and about | September 5, 2023

Vince ‘Wide Leg Linen Trousers’ – $251.00

This sort of outfit really takes me back to the early aughts when the heyday of Avril Lavigne’s flimsy cropped tank tops and oversized wide leg cargo pants dominated the scene. A very skater girl fall moment!

While this side of Labour Day also tends to be recognized as the unofficial end to summer and transition to fall, it can still be disconcerting to see such a heavy look when the sun’s still out and temps are still high. To logic her way into an autumnal outfit here, Taylor’s opted for pants made of breezy linen.

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

Get the look: Abercrombie, $54.99

Photo by Robert Kamau via Getty Images

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Out to dinner at Zero Bond | New York City, NY | August 17, 2023

Jennifer Zeuner ‘Tasha’ Earrings’ – $154.00
Ancosti ‘Patchwork Cap Sleeve Maxi Dress’ – $150.00
Jacquie Aiche ‘Rainbow Aura Quartz Necklace’ – $6,000.00
Louis Vuitton ‘Camera Box Bag’ – $3,450.00
The Row ‘Robin Booties’ – $1,680.00

There’s something quite Renaissance meets Disney princess in an autumnal wood meets modern trend look to this outfit. Which is to say that its mix of aesthetics to create something uniquely, delightfully ‘off’ but wonderful is what makes it a quintessential Taylor look.

In particular, the combination of a smaller indie brand like Ancosti, with a designer bag, and a trend-forward piece like a chunky sole boot is the embodiment of Taylor’s personal approach to fashion – a blend that is her own.

Speaking of the designer bag, Taylor is not a stranger to an LV monogram print bag. But this particular one – from the Fall 2023 runway – is her smallest so far. Her first was a larger tote from a limited collaboration with Christian Louboutin back in 2015. The second was a boxier ‘Cruiser’ she wore during some whirlwind summer travel in 2016. Here, she downsizes to a cute pocket-sized bag with the added refreshing factor of the contrast Reverse Monogram colourway that I think ties in neatly to the autumnal palette going on. And yes, I’m a proponent of mixing black and brown.

In the case of the black in this outfit – in a past life, Taylor may have worn this dress with flat, knee high boots. Or sky high nude pumps. Or two tone brogues (maybe a cream and cognac brown combo?). But here we see a nod to todays trends with a heavy, black, chunky sole stomp-worthy boot. Proof of the power of styling and accessorizing to truly change a look completely.