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Attending Republic Records after party | New York City, NY | August 28, 2022

Vrai ‘Signature V Band’ – $1,550.00
Nicole Rose Jewelry ‘Diamond Mix Cut Coil Ring’ – $5,195.00
Melissa Kaye ‘Aria Belle Ring’ – $4,950.00

Though hidden underneath her coat, Taylor was wearing a few new white gold rings for her after-party appearance. A nice complement to the star motif on her romper.

Worn with: Ananya earrings, Moschino romper, and Alexander McQueen heels

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Attending Republic Records after party | New York City, NY | August 28, 2022

Moschino romper – not available for purchase (pictured similar)

Tentatively from the two appearances we’ve seen, it’s really fascinating the juxtaposition of this level of glamour and glitz with what appears to be one of her most introspective and potentially dark works to date.

While Taylor has explored vintage styles in previous era’s (RED), this feels like a more luxe showgirl-esque version of that. And when placed in the context of an album that explores the intrusive thoughts or the secret highs that come at midnight, the style choice is made all the more fascinating.

Especially when we consider the high shine allure of ‘showgirl’ performance and production – it’s a life and a culture defined by a shiny, beautifully coiffed exterior that is often laminated over a seedier underbelly. Which (again, from what we know) seems to align with the darker narratives I suspect will be present on Midnights.

Which is to say, in short, I’m obsessed.

Worn with: Ananya earrings, Nicole Rose + Melissa Kaye rings, and Alexander McQueen heels

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Attending Republic Records after party | New York City, NY | August 28, 2022

Alexander McQueen ‘Butterfly Glitter Ankle Strap Platform Sandal’ – $1,090.00

This is such a fun true ‘party’ in ‘after party’ look that nods to the night’s earlier showgirl-esque red carpet outfit and also to her newly announced Midnights album with the star motif.

The shrugged jacket continues that touch of over-the-top ‘glam’ that seems to be a tentative theme to this era’s fashion. As do these platform sparkly sandals.

Worn with: Ananya earrings, Moschino romper, and Nicole Rose + Melissa Kaye rings

Get the look: Rachel Zoe platform, $110.00

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MTV Video Music Awards | Newark, NJ | August 28, 2022

Pat McGrath ‘Rose 001 The Essence’ – $86.00
Pat McGrath ‘Skin Fetish Sublime Perfection Primer’ – $45.00
Pat McGrath ‘Sublime Perfection Foundation in Light Medium 11’ – $68.00
Pat McGrath ‘Sublime Perfection Concealer in Light 7’- $34.00
Pat McGrath ‘Sublime Perfection Setting Powder in Light 1 and Light Medium 2’ – $39.00
Pat McGrath ‘Blurring Under-Eye Powder in Light’ – $32.00

I’m appreciative and grateful for Pat McGrath’s beauty work on Taylor last night – and for posting all. the. deets! It’s so fun to be able to have insight into the exact details of Taylor’s beauty lewks.

As I’ve had a moment to process and go over close up photos, my thoughts on beauty styling are the jewels are awesome choices (especially those earrings) and I generally love the makeup and glow.

But I do wish that in order to commit to the retro vibes and provide a cleaner finish around her forehead that her bangs were styled in finger curls and perhaps paring down the crystal appliques to a single one (or 2-3) at each corner of her eyes to further emphasize her signature cat eyeliner. That or instead of black liner, a fun silver glitter liner.

Worn with: Oscar de la Renta dress, Lorraine Schwartz jewelry, and Christian Louboutin sandals

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MTV Video Music Awards | Newark, NJ | August 28, 2022

Lorraine Schwartz earrings and rings

On a night of many surprises, one thing that didn’t surprise me was Taylor’s jewelry provider – the constant and wonderful Lorraine Schwartz. I particularly love that very modern and sharp shape of her drop diamond earrings.

Worn with: Oscar de la Renta dress, Pat McGrath makeup, and Christian Louboutin sandals

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MTV Video Music Awards | Newark, NJ | August 28, 2022

Pat McGrath ‘Mothership x Moonlit Seduction Palette’ – $128.00
Pat McGrath ‘Perma Precision Liquid Eyeliner’ – $28.00
Pat McGrath ‘FetishEYES Mascara’ – $32.00

Pat McGrath ‘Divine Blush in Nude Venus + Divine Rose’ – $39.00
Pat McGrath ‘Skin Fetish Highlighter + Balm Duo in Nude’ – $50.00

Pat McGrath ‘PermaGel Ultra Lip Pencil in Blood Lust + Deep Dive’ – $29.00
Pat McGrath ‘LiquiLUST Legendary Matte Lipstick in Elson 4’ – $32.00

The feeling when Pat McGrath does Taylor’s makeup and drops all. the. details.

Worn with: Oscar de la Renta dress, Lorraine Schwartz jewelry, and Christian Louboutin sandals

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MTV Video Music Awards | Newark, NJ | August 28, 2022

Christian Louboutin ‘Bombina Pampilla Sandal’ – $1,095.00 (similar)

While the dripping diamonds here are a great tie-in to the overall cascading effect of the dress, I think the similar idea of the ‘Planetava’ style Louboutins would have accomplished the same goal in a slightly cleaner silhouette.

Worn with: Oscar de la Renta dress, Pat McGrath makeup x2, and Lorraine Schwartz jewelry

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MTV Video Music Awards | Newark, NJ | August 28, 2022

Oscar de la Renta Resort 2023 – $24,990.00

I have the privilege to be able to write this caption with the full knowledge of Midnights on my mind and the awareness that this look is likely a taster of a rich, luxe, almost showgirl glam style. A new, womanly version of the retro and vintage fashion she has favoured for more than a decade – but elevated. And with a fun, vampy sex appeal.

I’m of the opinion this is not a reference to her 2009 dress from this same event – it’s distinctly different in silhouette and composition. Perhaps if I were looking at an asymmetrical one-shoulder gown with diagonal swathes of glitter – I could see the comparison. But this feels far removed from that Kaufmanfranco of 13 years prior.

While this dripping diamond mini has a lot of vintage feels (I love the halter neck), it doesn’t feel right to draw comparison to vintage Taylor fashion. This is a sartorial step in a fresh, new direction to reflect a new body of work and a new period in her life. Let’s consider and treat it as such.

Worn with: Pat McGrath makeup x2, Lorraine Schwartz jewelry, and Christian Louboutin sandals

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TSS PREDICTIONS: 2022 MTV VMAs

With the MTV VMAs on August 28 and Taylor up for significant awards (alongside some highly suspicious attention and promotion being paid to the award ceremony) – it just feels like the time is right for some kind of news and an appearance from her.

Historically, her fashion at the VMAs has been very mixed. Most years it’s fun and short and edgy or interesting – an opportunity to step outside of the box. See: The Incident. Or: The Incident 2.0. But she’s also had two years where she’s opted inside the box with two full-length formal gowns. Add in the fact that Taylor’s style is such a mystery these days without a clear aesthetic driven by a single project – your guess is quite literally as good as mine for this award show.

(Pro Tip: If you want more fashion content, TSS Patreon subscribers get exclusive early access to predictions post plus extra bonus content).

But, as always, I’ll do my best.

And with that, here we go.

  • Christian Siriano Resort 2023: I really like this frock because it offers a best of multiple worlds scenario and ticks a lot of different boxes where Taylor’s style has lived over the years. Feminine and soft (the shoulder bows), a little sexy and saucy (the bustier cups and thigh slit), powerful and tailored (the neutral palette and elegant styling). I would love to see this with Taylor’s signature red lip and a shiny wavy pony with a black velvet hair ribbon for a kicky and girlish touch. And why not go all the way with some Aquazzura bow pumps to finish it off.
  • Alice + Olivia Spring 2022: This gown feels familiar but also fresh. The cutouts and delicate straps are reminiscent of her Balmain jumpsuit at the 2015 BBMAs and the skirt and overall shimmer a reminder of her most recent appearance at the BRITs. I appreciate that this is chic, clean, minimal, but with a bit of skin. A perfect balance for Taylor’s fashionable comfort level seems to be as of late.
  • Naeem Khan Resort 2023: Given Taylor’s love of trousers lately, I feel we are massively overdue for a suited red carpet moment. Taylor has previously worn a suit to the MTV VMAs – but that was a literal decade ago. I think it’s time to revisit the suit. We also know that Taylor has embraced over-the-top prints at this particular event in the past. Again, see: Incident 2.0. So a romantic floral (which is something she has worn many a time in the form of a tea-length fit/flare dress) seems very on brand. I would do a deep side part with old Hollywood waves, modern emerald-studded ear climbers, and a red lip.
  • Erdem Resort 2023: A kind of meeting in the middle between the Siriano and the Naeem Khan picks. A neutral colour palette but with romantic floral fabric and in a separates silhouette. This feels edgy but mature but feminine – all things that I think Taylor wants to accomplish in the here and now and specifically is appropriate for this particular awards ceremony. Tousled hair, smudged eyeliner and shadow, and a popsicle stained orange tangy lip with diamond studs and black diamond ear cuffs plus patent burgundy sandals would be my choices for styling.

What do you think of my picks? Do you have a favourite? And most importantly, do you think Taylor is showing up at all? Fingers crossed!