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Time 2023 Person of the Year | December 6, 2023

Ralph Lauren Collection ‘Tuxedo Jacket’ – $2,490.00

I love the combination here of polished three-piece tuxedo suiting with casual denim jeans.

By my eye, it appears Taylor might be wearing a cropped version of this RL Collection jacket.

Worn with: Ralph Lauren Collection shirt + vest and Polo Ralph Lauren jeans

Photo by Inez and Vinoodh for Time

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Time 2023 Person of the Year | December 6, 2023

Bardot ‘Roll Neck Knit Bodysuit’ – $69.00

I think we have all collectively lived so many lives within the Swiftieverse in the year 2023. This year has given us so much.

But the greatest gift of all? The editorial photoshoot debut of one Benji Button.

Onto the fashion! Given the high leg cut and pairing with shiny black tights, this look gives me very Madonna vibes. In other photos of her in this simple ribbed bodysuit, we see Taylor flexing her arms – to me a callout to the Eras Tour choreography for “The Man” and of course embodying her power and femininity.

I love that the shoot’s team worked together to give a look that’s pared back and a play on ballet femininity and strength (styled by Heidi Bivens) while also providing references to some of Taylor’s most iconic beauty signatures like tousled curls (by Holli Smith) that feel closer to the natural texture of her debut era, and a bold red lip (by Diane Kendal).

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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Out and about | New York City, NY | December 5, 2023

Sheertex ‘Modern Diamond Sheer Tights’ – $99.00 $35.00 (on sale)

There are truly few things that give me fashion flashback in Taylor’s closet staples like a pair of designed tights which lift me all the way to her earliest days even through to now. When wearing designed tights like these, Taylor’s also not been one to be afraid of layering them with other patterns – like the plaid you see here.

Also note the signature high/low on display here in terms of designers.

Worn with: Stella McCartney coat and skirt, VRAI + Jacquie Aiche + Louis Vuitton jewelry, Jimmy Choo x Jean Paul Gaultier heels

Photo by James Devaney via Getty

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Out and about | New York City, NY | December 5, 2023

Jimmy Choo x Jean Paul Gaultier ‘Leather Wedge Pumps’ – $2,450.00

One of Taylor’s go-to heel brands is Jimmy Choo so opting for this brand doesn’t necessarily come as a surprise, but what does is the bolder choice to go with this limited edition shoe co-designed with JPG.

The design takes what’s otherwise a regular pointed black pump and gives it a twist with a plexi wedge heel – modernizing the stiletto and also giving it an artistic form.

The pointed toe is also not typically something that Taylor opts for, but its elongated silhouette once again (to me) calls back to that Miss Americana red carpet outing where she also (again, rare occasion) opted for pointed toe boots. Given that in the last week we’ve seen multiple high profile business accomplishments in the press by Taylor (highest grossing tour by Billboard, Most Intriguing Person by People, 5th most powerful woman in the world by Forbes), it doesn’t feel like a stretch to me that she’d be revelling in a shoe that feels more powerful by extension and business-y.

Another fun fact? The wedge was designed to reference the “iconic architectural landmarks of the two brands’ home cities: Paris with the Tour Eiffel and London with Big Ben asymmetrically encased inside each heel.” An interesting homage.

Worn with: Stella McCartney coat and skirt, VRAI + Jacquie Aiche + Louis Vuitton jewelry, and Sheertex tights

Photo by James Devaney via Getty

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Out and about | New York City, NY | December 5, 2023

Stella McCartney ‘Frayed Checked Wool Blend Tweed Mini Skirt’ – $975.00

Just the other day in stories I was talking about the history of Taylor and mini skirts and how – especially as we approach the end of 2023 – that this year has seen quite a revival for them in her candid fashion.

While it’s fun to see Taylor’s style come to fruition in the moment, I very much think that consideration for an ‘era’ as a whole can really only be done in hindsight once we have a birds eye view of the time period in order to be able to really pull out trends, commonalities, and patterns.

In this current moment, a wool tweed mini (esp paired with designed tights – another closet staple Taylor has a long history with) feels preppy, smart, and wintery. Almost Gossip Girl-esque!

Worn with: Stella McCartney coat, VRAI + Jacquie Aiche + Louis Vuitton jewelry, Sheertex tights, Jimmy Choo x Jean Paul Gaultier heels

Photo by James Devaney via Getty

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Out and about | New York City, NY | December 5, 2023

Stella McCartney ‘Double Breasted Wool Blend Tweed Coat’ – $2,900.00

While Stella McCartney is very much a Lover era brand (courtesy of Taylor’s fashion collaboration with the brand), a matching set like this gives me #1989 flashbacks – an era known predominantly for the power of a co-ordinated ‘fit.

Still riding the high of 1989 (Taylor’s Version) this very much to me feels like an elevated, business-esque, modern take on the crop tops and skirts of her 2014 self. But built for cooler weather.

It also to me harkens back to her neck to foot plaid look for the Miss Americana premiere at Sundance which also featured a wool check plaid.

Worn with: Stella McCartney coat, VRAI + Jacquie Aiche + Louis Vuitton jewelry, Sheertex tights, Jimmy Choo x Jean Paul Gaultier heels

Get the look: Abercrombie, $154 (on sale)

Photo by James Devaney via Getty

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At Lambeau Field | Green Bay, WI | December 3, 2023

Vrai ‘Linked Tennis Earring’ – $1,990.00

As Taylor has been expanding her forays into jewelry stacking, it’s also been fun to see what brands she turns to when experimenting with her jewelry. The last time we saw Taylor wear Vrai was June 2022 at her Tribeca Film Festival appearance.

Worn with: Cartier necklace, Stella McCartney coat, Louis Vuitton skirt, and Stuart Weitzman boots

Photo by Stacy Revere for Getty

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At Lambeau Field | Green Bay, WI | December 3, 2023

Louis Vuitton ‘Strap Detail Mini Wrap Skirt’ – $3,400.00

As we approach the end of the year and I start to turn my gaze backwards on 2023’s fashion to pull together my annual list of Favourite Outfits, in addition to really thinking about what ‘fits to include on my last of faves I also like to think about trending items and patterns that crop up.

All this to say that I feel like in looking back on this year, one such trend might just be the mini skirt. Taylor has worn many over the course of her career, but she’s really been rocking many this fall at least – especially paired with tall boots.

Worn with: VRAI earrings, Cartier necklace, Stella McCartney coat, and Stuart Weitzman boots

Photo by Mark Hoffman for the Milwaukee Journal Sentinel

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At Lambeau Field | Green Bay, WI | December 3, 2023

Stuart Weitzman ‘Vidaland Boot’ – $995.00

Two main things of note with these (incredible) OTK boots.

As noted by the distinctive tie at the back and confirmed to me by the brand these are Stuart Weitzman boots. While Taylor has worn this brand many times over the years, for me they have an unshakeable place solidly in the 1989 Era for their sponsorship of that album’s associated tour and providing many a heel for Taylor to strut in on the 1989 Tour stage. Which feels appropriate given the recent release of 1989 (Taylor’s Version).

Secondly, what I find so fun to watch regarding Taylor’s game day fashion evolution has been observing her growing confidence and power as she grows more comfortable entering these football stadiums as guest and watcher. Her first foray saw her in casual denim shorts and sneaker – unassuming and laidback and sweet. To me, opting for a big coat (wintry weather aside) and tall black leather boots feels powerful and sure. It evokes a voluminous and large presence that cannot be ignored and demands to be seen.

Worn with: VRAI earrings, Cartier necklace, Stella McCartney coat, and Louis Vuitton skirt