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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!

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Out to dinner with Joe Alwyn and Lena Dunham | New York City, NY | August 23, 2022

Rouje ‘Gabinette Dress’ – €180.00

Nice of Taylor to post a TikTok of her wearing this dress originally first seen in pap photos taken of her grabbing dinner in New York just a few days prior.

Worn with: Burga phone case

Get the look: Max Studio, $33.74

Editor’s Note: Posting without photographs due to the photo agency responsible for the pap images.

Editor’s Note 2: Updating with photo taken from TikTok published August 28.

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Camping (August 21-23)

Hi TSSers!

Just a heads up that in case Taylor decides to show up over the course of the above noted days – you know who to thank. 😉

I’ll be taking some time away for what seems to be my annual digital detox to unplug and enjoy nature, campfires, and some nice company.

I’ll be back in the swing of things late Tuesday/early Wednesday.

Thinking of you all and hoping you’ve all had a lovely August that has sipped away like a bottle of wine – so to speak.

Sincerely,
– Sarah

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“30, nerdy, and worthy” (x) | July 22, 2022

Christy Dawn ‘Lianne Dress in Colorblocked Crimson’ – $575.00

My entire heart! It seems almost impossible that this friendship has spanned as long as it has (or that Selena really is 30 this year) – but we got adorable Taylena content as Taylor celebrated this momentous birthday with her dear friend in this mixed print dress by one of her favoured sustainable dress brands.

Worn with: Christy Dawn dress

Get the look: ASOS, $26.00

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Performing with Haim | London, England | July 21, 2022

Christian Louboutin ‘Izamayeah 130 Platform Boots’ – $1,295.00

While I almost expected Taylor to go full LV with this lewk, she swerved a little to opt instead for a pair of platform Louboutins. I appreciate that the tight upper on this boot probably fit very nicely under the wider legs of her leather pants.

Worn with: Louis Vuitton tank top and pants

Get the look: Steve Madden, $149.95