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Eras Tour Film premiere | Los Angeles, CA | October 11, 2023

Oscar de la Renta ‘Cutout Floral Gown’ – $11,990.00 $5,995.00

In my predictions post for this premiere on the TSS Patreon I selected a different dress by Oscar de la Renta (a longtime favourite designer of Taylors) and noted that my ideal styling with said gown would be a “red lip and pinned faux bob with tons of bangles and chandelier diamond earrings … for an old Hollywood glam feel.”

Needless to say, I support and love this outing.

It’s dramatic and ladylike while also honouring and extending the #1989Blue precedent she set during the final stages of the U.S. 2023 leg of the Eras Tour. Dressing to a colour palette is a perfect connector and reminder to bridge both the event at hand of the concert tour movie and her most pressing upcoming record with 1989 (Taylor’s Version) set to release on October 27.

All in, this is a beautiful gown and perhaps one of her best appearances ever. The elegant styling (dainty rings and eye-popping matching diamond tennis necklace and bracelet) were the perfect choices. And maybe I’m just jealous that Taylor is someone who can pull off blue eyeshadow (any other brown eyed girls who were told that blue makeup would make your eyes pop and subsequently did not look like Taylor Swift when you tried a powder blue shadow look? anyone? just me?).

Designer Fernando Garcia also noted during the Resort 2023 collection’s presentation that “cut-outs have become a go-to for our customer”. The ones on this gown feel like an organic nod to the spliced crop tops that were signature to the original 1989 fashion run in 2014. But here, they’re more organic and integrated into the design – a natural part of fully blossoming some might say. And if you missed the subtle cut-out nod, there’s always the faux bob that might double take you into believing you were back in 2014/15 and also nods to the messy, slightly undone style seen on the 1989 TV cover.

As backstory, it should surprise no one that this particular collection happened to debut on June 13, 2022 at (where else) the New York Botanical Garden.

Worn with: Cartier necklace + Anabela Chan bracelets, Cartier studs + Cathy Waterman + Akillis + Anabela Chan rings, and Giuseppe Zanotti heels

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The Eras Tour | Midnights section

Oscar de la Renta custom

As a former dancer myself who’s done a chair dance, I respect and feel a kinship towards Taylor challenging herself with more intricate and highly choreographed numbers on this tour. It’s even more impressive when you consider that the number appears on the tour’s final section of a three hour show.

The fringe on this midnight blue bodysuit drips beautifully over her hips here and plays multiple roles. Serving to mimic raindrops for “Midnight Rain”, a fun twirly moment worthy of strutting and spinning during “Bejeweled”, and to add a sensual tasseled burlesque feel during that aforementioned chair dance of “Vigilante Shit”. Plus it also feels kind of cheeky western glam.

Worn with: Christian Louboutin boots

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The Eras Tour | Midnights section

Oscar de la Renta custom

The most direct reference to present Midnights fashion comes via this faux fur jacket – a designer take on the Free People faux she wears in the “Lavender Haze” music video.

The number of times outerwear is used as a method of quick change to impact the silhouette of a look (the duster added during her RED set) or shift the visual direction of an outfit (the Boss blazer added for “The Man”) feels like a fun folkmore reference to the chic outerwear that dominated those visuals.

Worn with: Christian Louboutin boots

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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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63rd Annual Grammy Awards | Los Angeles, CA | March 14, 2021

Oscar de la Renta ‘Floral Embroidered Tulle Mini Dress’ – $8,990.00

While none of my predictions included a mini (I definitely had an elegant full-length gown in mind for this big night), I did accurately predict the brand so I’ll take a partial win for that. 

My predictions also noted that there was a possibility for the ‘fit to reference Lover, and I definitely think this lush floral dress would not have been out of place during that time. Taylor looks like she walked out of a flower field and the petal pink soft makeup is the perfect complement. 

It’s romantic, it’s whimsical, and while being colourful it still somehow neatly bridges Lover to folklore in a very lovely way. The changes made to it from the original runway presentation include floaty cuffs and a slightly longer hem. 

I could easily see this dress being worn to the AMAs (where Taylor has a stronger history of wearing minis), so while I’m still mentally attached to the concept of a long, elegant and impactful gown, this short and sweet mini as-is is very beautiful and also notably is an appropriate choice given the timeshift of the awards ceremony to be situated more in the springtime. 

Worn with: Cathy Waterman earrings + rings and Christian Louboutin sandals

Get the look: EFINNY dress, $28.99

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63rd Annual Grammy Awards | Los Angeles, CA | March 14, 2021

Oscar de la Renta ‘Floral Embroidered Tulle Mini Dress’ – $8,990.00

While none of my predictions included a mini (I definitely had an elegant full-length gown in mind for this big night), I did accurately predict the brand so I’ll take a partial win for that. 

My predictions also noted that there was a possibility for the ‘fit to reference Lover, and I definitely think this lush floral dress would not have been out of place during that time. Taylor looks like she walked out of a flower field and the petal pink soft makeup is the perfect complement. 

It’s romantic, it’s whimsical, and while being colourful it still somehow neatly bridges Lover to folklore in a very lovely way. The changes made to it from the original runway presentation include floaty cuffs and a slightly longer hem. 

I could easily see this dress being worn to the AMAs (where Taylor has a stronger history of wearing minis), so while I’m still mentally attached to the concept of a long, elegant and impactful gown, this short and sweet mini as-is is very beautiful and also notably is an appropriate choice given the timeshift of the awards ceremony to be situated more in the springtime. 

Worn with: Cathy Waterman earrings + rings and Christian Louboutin sandals

Get the look: EFINNY dress, $28.99

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CATS premiere | New York City, NY | December 16, 2019

Oscar de la Renta ‘Fil Coupé Gown’ – $17,990.00 (sold out)

Fit for a princess. 

Given Taylor’s role in the film and that this premiere is her first truly big budget film making its debut, it’s understandable why she and her team would want to go the classic, beautiful princess route instead of something more experimental. 

The embroidery is beautiful and I love her beauty look (the red lip here is slightly darker than her classic blue red) and jewels. 

The pockets and contrast side panel are also lovely touches to bring some intrigue/interest to what otherwise amounts to a very lovely premiere gown that also subtly nods to Christmas with its hue and rich indulgent embroidery. 

There’s also something about this look that is incredibly reminiscent of Taylor’s style of her youth. The red carpet look that immediately comes to mind is her farewell to country music in red Elie Saab at the 2013 CMAs.

Worn with: Maxior Joias + Beladora + Borgioni jewelry and Chloe Gosselin sandals

Get the look: Lord & Taylor, $173.40

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CATS premiere | New York City, NY | December 16, 2019

Oscar de la Renta ‘Fil Coupé Gown’ – $17,990.00 (sold out)

Fit for a princess. 

Given Taylor’s role in the film and that this premiere is her first truly big budget film making its debut, it’s understandable why she and her team would want to go the classic, beautiful princess route instead of something more experimental. 

The embroidery is beautiful and I love her beauty look (the red lip here is slightly darker than her classic blue red) and jewels. 

The pockets and contrast side panel are also lovely touches to bring some intrigue/interest to what otherwise amounts to a very lovely premiere gown that also subtly nods to Christmas with its hue and rich indulgent embroidery. 

There’s also something about this look that is incredibly reminiscent of Taylor’s style of her youth. The red carpet look that immediately comes to mind is her farewell to country music in red Elie Saab at the 2013 CMAs.

Worn with: Maxior Joias + Beladora + Borgioni jewelry and Chloe Gosselin sandals

Get the look: Lord & Taylor, $173.40