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Out and about | New York City, NY | December 13, 2023

Clio Peppiatt ‘Lucina Embellished Stretch Mesh Mini Dress’ – $2,335.00

For the last few days I’ve thought a lot about how there’s been a certain uptick in the level of ‘glam’ in Taylor’s looks that harkens back to the early days of Midnights promotion. A time period when Taylor’s style was a two-tone mix of a patchouli hazed 70s apartment stuffed to the ceiling with well-loved vinyls over which a veneer of pinned up showgirl was laminated. Short hems, high heels, faux furs, dripping diamonds. I always felt this was an appropriate way to create a visual extension of an album that is positively full of emotions that are nuanced, complex, and that seem to be in direct opposition to one another even over the course of one track to the next. Over a year out from that album, much about Taylor’s life (professionally and personally) has been completely upended.

So to see her here now, effectively bookending Midnights fashion in a look that’s dark and ruminating and moonlit and celestial and mysterious yet sparkly and glam and alluring … it feels all the more appropriate on her birthday of all days. Adding another year of life to your experience tally often creates moments for reflection and to sift through memories – good and bad. Which sounds very much like the ethos of Midnights if you ask me.

On its surface, this is a fun party look (in a new-to-her brand which is an exciting new addition to her designer roster) that’s perfectly coordinated between the silver embellishments scattered like the night sky across her dress, to her bag, and even into the details of her shoes. Plus the extra shine factor of her jewels.

But like with any Taylor look, it’s one that gives me pause and makes me think of the context to what got us here and also to where she may be going.

Worn with: Anine Bing jacket, Messika earrings, Mazin Jewels necklace, Aquazzura bag and heels

Get the look: Topshop, $278.00

Photo by Gotham via Getty Images

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Out and about | New York City, NY | December 6, 2023

The Row ‘Constantine Gown’ – $2,490.00 $1,245.00

To support her friend Emma Stone at the premiere of her film Poor Things, I love that Taylor went chic but glam in all black – a decision I feel is rarely a bad one. She kept things simple in a slinky, floor-length black dress by The Row which is fast becoming one of her most worn brands this year.

Worn with: VRAI earrings, Charlotte Simone coat, Naeem Khan clutch and Giuseppe Zanotti heels

Photo by Gotham via Getty Images

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Time 2023 Person of the Year | December 6, 2023

Alaïa ‘Convertible Chenille Gown’ – $3,320.00

An a-what-a?

The entire shoot feels this way to me, but this pose in particular coalesces to represent the ethos of the piece in one frame: Feminine power and artistry. I can’t help but imagine though what this moment could have looked like if styled with the removable hood and asymmetric sleeve options that it was originally designed with. But ultimately the choice to have her curls as a defining calling card feel like the ‘right’ option for Taylor and to center her most identifiable human features for an inherently ‘personable’ piece.

Like all things, the ‘accessory’ choices (a fluffy cat, a coordinating black guitar) in this shoot feel highly intentional to me as symbols of Taylor’s personality and work.

Photo by Inez and Vinoodh for Time

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Time 2023 Person of the Year | December 6, 2023

Area ‘Crystal Embellished Gown’ – $1,900.00

Just yesterday I commented on what I perceived to be Taylor’s level of comfort and confidence to exude equal parts power, ease, openness, and femininity – her fashion being an extension of that and an opportunity for her to communicate that without saying a word.

This Time piece, the first proper sit down interview I feel we’ve had in some time, is the culmination of that. The feature is sweeping and possibly one of the best and fullest profiles we’ve had in some time that I’ll be taking a lot of time to mull over.

Given how long the interviewer has spoken with her over the course of this year for this piece, I can’t help but wonder if the usage of Area as a designer here is intentional as this brand has played a fashion role in a few of Taylor’s most memorable outfits this year. First in the form of embellished butterfly jeans in a post-split pap walk. Second in embellished shorts on ‘home’ turf at a Chiefs vs Jets game at a stadium she’s sold out three times this year.

Photo by Inez and Vinoodh for Time

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RENAISSANCE: A Film By Beyoncé premiere | London, England | November 30, 2023

Balmain custom

When it became apparent that Taylor was going to repay the favour Beyoncé did her by also appearing at the ‘Renaissance: A Film by Beyoncé’ London premiere, it felt all but certain she would appear in an appropriate #RenaissanceSilver gown – and oh did she deliver.

I personally have a soft spot for a column gown and the clean, elegant silhouette it offers. One of my previous all time favourite Taylor red carpets happens to be a silver metallic column gown (the Gucci Première gown of the 2014 Grammys).

Where that Grammys look was styled almost sweetly with a ponytail, soft smoky eyes, and a pink nude lip – this take on a silver gown brings more Hollywood glam thanks to the deep side part, sexy waves, and bold red lip. To my eye, it actually feels like a great continuation of the retro glam girl aesthetic we first were served at the outset of the Midnights era – which feels appropriate given the release of “You’re Losing Me” doesn’t it?

The gown also contains references to Balmain’s Spring/Summer 2024 collection, as seen in the rosette detail on the left bust and strap. Olivier Rousteing, creative director of Balmain, said that the floral motif throughout the collection was to deepen the house and its identity with French luxury. “These roses have thorns, you know?” he said. “The Balmain rose cannot just be a romantic rose. There is also toughness and strength. So it’s about love, it’s about colors, happiness and joy. But it’s also about torment! Just because you are tormented it doesn’t mean you need to do a black collection.” It’s very Swiftian.

Of course, as per usual – Taylor thinks of everything when it comes to selecting the designer to bring a look to life. Balmain having played a pivotal role in many of Beyoncé’s looks that she wore on the Renaissance World Tour. What a thoughtful homage to create that design crossover that beautifully pays respect to the many silver custom looks Bey wears on her stage while still feeling entirely Taylor. Very well played.

Worn with: Anita Ko jewelry and Giuseppe Zanotti heels

Photo by Getty

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Out and about | New York City, NY | October 26, 2023

Stella McCartney ‘Oversized Cotton Rugby Polo Shirt’ – $850.00

This dress is so comically Taylor. From the designer choice to feeling like an evolution of her preppy schoolgirl style that’s been a mainstay aesthetic in her outfit repertoire since Fearless days. But this version takes styling cues from the Stella runway, wearing this oversized shirt as a mini dress with tall boots.

The horse girl energy between the RL cap and the equestrian take on a school uniform emblem are also very Taylor.

A fun note about this particular Stella collection is its further push towards sustainability with most of the pieces taking material sourcing from upcycled or overstock fabrics.

Worn with: Ralph Lauren hat, Tod’s bag, and Prada boots

Get the look: H&M, $34.99

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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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Out and about | New York City, NY | September 30, 2023

Aritzia ‘Trix Dress’ – $148.00

The power of styling! As was the case earlier in the day with Taylor’s fall uniform pairing of navy sweater + plaid skirt, we saw Taylor change into a classic LBD as a second outfit for the day to go out for dinner. Taylor’s worn many LBDs over the years, but the styling here with a twisted piecey updo, belt, and layers of gold jewelry feel accurate to her present-day style. The cohesion of gold hardware all throughout also pleases me as a yellow gold lover.

Worn with: Jacquie Aiche jewelry, B-low the Belt belt, Ralph Lauren bag

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Out to dinner with Sophie Turner | New York City, NY | September 19, 2023

Reformation ‘Radlee Knit Dress’ – $98.00

I love the fall-forward palette here (Taylor does fall fashion so well). Recognizing that the duster/long denim jacket here is the #fashun moment and that its proportion balances out the tall boots with the short dress, I wonder if in terms of silhouette and overall colour palette a washed black denim jacket (oversized) would have played better.

Or even a long wool camel coat for those fall leaves vibes.

Worn with: Mckenzie Liataud necklace, EB Denim jacket, Luana Italy bag, and Reformation boots

Photo by Pap Culture

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MTV Video Music Awards after party | September 12, 2023

EB Denim ‘Polka Dress’ – $480.00 $336.00

What an incredibly fun after party dress. It’s sassy, very short, and feels like another 90s throwback (who else remembers all the ultra #FASHUN denim styles that hit the red carpet then?). In some ways, I can actually see how this could have theoretically worked at the award show itself, with some tweaks. 

The addition of the red lip here does a great job signaling “party!” but I do wonder what a sleek ponytail would have done for the look.

Worn with: Vintage necklaceAlessandra Camilla Milano + Mindi Mond + Natasha Schweitzer + Nicole Rose jewelryAquazzura bag, and Aquazzura sandals