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65th Annual Grammy Awards | Los Angeles, CA | February 5, 2023

Roberto Cavalli custom

Rather than look backward and pay homage to RED and its TV in honour of her SOTY nomination for “All Too Well (10 Minute Version)”, Taylor went with a more Midnights-appropriate look at the Grammys.

This midnight navy colour is beautiful on Taylor – a hue she rarely wears. Combined with the starry night embellishments, the looks feels appropriate to the late night theme of Midnights. I think I could envision this as a gown with side cut outs and a slit – or with a completely open back. With the current silhouette, the reference to the co-ordinating sets and crop tops of the 1989 era immediately came to my mind.

I would have loved to have seen the hood (as pictured in the original Fausto Puglisi-designed sketch) but am not mad by its omission to instead commit to a high wattage, statement earring moment. Continuing to prove that styling can really make or break a look.

The slightly mussed, twisted bun was a nice way to counterbalance all the sharp lines of the ensemble. See those strong shoulders, the geometric earrings, the horizontal slice of her torso. An updo was definitely needed with that high neck but it was a great choice to give a little looseness and her makeup was so well-coordinated to the rest of the look.

Worn with: Lorraine Schwartz earrings and rings and Giuseppe Zanotti heels

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Directors on Directors | December 12, 2022

Brunello Cucinelli ‘Linen and Silk Tweed Miniskirt’ – $1,595.00

I love this very cozy combination of oversized sweater and check skirt – but it strikes an interesting juxtaposition for the interview given Martin McDonagh’s sharper suit. It’s a very Taylor outfit (check the burgundy loafers in the full body shot) that plays with layering, interesting colour combinations, and schoolgirl accents (which checks the boxes for a lot of her street style moments) – but a chic trouser set would not have been unwelcomed by me for this particular occasion.

As an aside, whether intentional or not, the smart navy colour story between the two of them interplays nicely on screen as they go back and forth talking about their craft (Aside on the aside: I could listen to Taylor talk about her creative passions for hours!).

Worn with: The Row sweater, Jennifer Zeuner earrings, and Prada loafers

Get the look: Max Studio, $29.99

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Midnights Mayhem with Me | October 7, 2022

Acne Studios ‘Corduroy Skirt’ – $380.00

It’s been the most fun just to see Taylor’s fashion again. Her relationship to the invasive nature of candid street photography is understandable, but it warms my heart to be able to see her style come through in a way that she can control for a project that she’s obviously so proud of. Forgive the emotional sidebar – it just fills my heart with so much joy.

Now to the ‘fit itself – it should come as no surprise that this quickly skyrocketed in my rankings of ‘Mayhem’ outfits. The interplay of both similar ribbing in the materials creates a seamless throughline for the outfit – supported by the overall mossy green(!!!) tonal vibes. But it’s the sheen of each fabric offsets them from one another so each piece is distinct, but complementary.

Get the look: Goodnight Macaron, $58.00

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2021 BRIT Awards | London, England | May 11, 2021 

Miu Miu custom top and skirt 

She couldn’t have been more clear that 1989 (Taylor’s Version) was next without cutting her hair back into that era’s signature bob, don’t you think? 

I jokingly noted in Monday’s predictions post to the TSS Patreon that it wouldn’t surprise me if Taylor made some allusion to the RED album given she’s already [seemingly] dropped hints about 1989 with the “Wildest Dreams” snippet and Speak Now with her usage of three emojis across her social media, that why wouldn’t she also throw in some RED hints too to really mix things up. Enter Taylor in sleek long hair and doing away with the charming curly fringe we’ve been seeing for the folkmore era. I think she still pulls this cut and texture off so well. 

Going back in my DMs, there were many early mentions of gree(eeeeeee)n in Taylor’s outfit but I think that boils down to the filter she applied for her sneak peek Instagram posts. The actual red carpet lewk is closer to a silver or a pale pale pale mint blue, to my discerning gaze. 

But to the lewk itself! At its core, it’s a 1989-friendly crop top with a more sophisticated skirt. Where her two-tone colourful Versace lewk at the 2016 Grammys (aka the curtain call of the 1989 era) was Malibu Barbie chic, this feels as subdued and refined as one can be when you’re wearing a crystal embellished crop top. 

At first with only that Instagram photo to go off of, I had feared that the bottom half of the lewk would be a pair of shorts or skort or a full ballroom skirt. Catch me being pleasantly surprised driving back from the wilderness to learn that it was this more fitted full-length skirt that brings to mind one of my favourite silhouettes on Taylor – the column. She pulls it off well and I think this is a very fresh take and an appropriate update to what was her signature 1989 style. 

The embellishment detail on the skirt and top are so intricate and lovely, that the only nitpick I think I could make is that given the iridescent way the crystals capture the light leans more purple/lilac or cool pink I think I would have loved to have seen that reflected in the lip. 

Otherwise, this is a very lovely outing for Taylor that achieves its objective well: Ushering in the next phase of the re-records era. 

Worn with: Jessica McCormack earrings, Jessie Thomas + Ananya + Astley Clark + Sophie Bille Brae rings, and Tiffany & Co bracelet, and Miu Miu sandals