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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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Out and about | New York City, NY | October 15, 2023

Louis Vuitton ‘Star Trail Boots’ – $1,760.00 (similar)

One thing about Taylor is that she loves a chunky boot and has for years. She’s worn many iterations of an edgy black lace up combat-style boot.

This particular pair has a long history in Taylor’s closet, hailing from the brand’s Fall 2016 collection which Taylor happened to wear the night before the Met Gala 2016 when she was co-chair of the event as a guest of LV.

Worn with: Maria Tash earrings, Alessandra Camilla Milano earrings, Jean Paul Gaultier top, Balenciaga corset, Roger Vivier bag, and Khaite skirt

Also worn: May 1, 2016

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Out and about | New York City, NY | October 3, 2023

Louis Vuitton ‘Camera Box Bag’ – $3,450.00

For those perhaps not aware or even blown away by Taylor’s ongoing carrying of this cute little LV bag (understandable given repeating fashion in the celeb world is typically a Kate Sanders-worthy no no) – it’s a key part of what I love about Taylor’s fashion is just how often she keeps things in her closet and rotates them. Back in the original 1989 era, she’d carry a nude bag of choice (often D&G or Prada) for months on end before switching to something new.

Worn with: Still Here hat, Free People shirt, Free People socks, and New Balance x Ganni sneakers

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Out and about | New York City, NY | September 8, 2023

Foundrae ‘Sister Hook Choker’ – $6,365.00
Foundrae ‘Forever & Always A Pair Oval Pendant’ – $1,450.00
Sandy Liang ‘Paris Skort’ – $625.00
Louis Vuitton ‘Camera Box Bag’ – $3,450.00
Gucci ‘Half Horsebit Almond Toe Boots’ – $905.42

One thing I love about this outfit is the tension of shapes and textures. The soft, angular swoop of her asymmetric top, knife pleats of her skort, and the sharp boxy lines of her LV camera bag all create certain, strong lines. These all work in direct contrast to the mussed, textured curls we see here that prevent it all from being too put together and polished.

I’m not one to look a gift skort in the mouth, so I won’t be reading into the “Paris” Easter Egg of it all. Especially one as chic as this. Any outfit defined by some sharp pleats and black is perfect in my books.

Let us instead admire how the confidence of an inner pair of shorts has given us all the gift of Taylor’s killer legs thanks to short hemlines.

If I had to, and could, copy and paste an outfit in its entirety on my body from recent Taylor history – it would be this one. At my core, I’m a girl who loves neutrals and polish served with a side of edge. And you all know I’m a proponent of the sandwich style (that is, to match two elements of an outfit between a contrasting colour).

Just add a blazer and we’re golden.

Get the look: Emory Park skort, $56.00 and Gap boots, $134.00

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Out to dinner at Zero Bond | New York City, NY | August 17, 2023

Jennifer Zeuner ‘Tasha’ Earrings’ – $154.00
Ancosti ‘Patchwork Cap Sleeve Maxi Dress’ – $150.00
Jacquie Aiche ‘Rainbow Aura Quartz Necklace’ – $6,000.00
Louis Vuitton ‘Camera Box Bag’ – $3,450.00
The Row ‘Robin Booties’ – $1,680.00

There’s something quite Renaissance meets Disney princess in an autumnal wood meets modern trend look to this outfit. Which is to say that its mix of aesthetics to create something uniquely, delightfully ‘off’ but wonderful is what makes it a quintessential Taylor look.

In particular, the combination of a smaller indie brand like Ancosti, with a designer bag, and a trend-forward piece like a chunky sole boot is the embodiment of Taylor’s personal approach to fashion – a blend that is her own.

Speaking of the designer bag, Taylor is not a stranger to an LV monogram print bag. But this particular one – from the Fall 2023 runway – is her smallest so far. Her first was a larger tote from a limited collaboration with Christian Louboutin back in 2015. The second was a boxier ‘Cruiser’ she wore during some whirlwind summer travel in 2016. Here, she downsizes to a cute pocket-sized bag with the added refreshing factor of the contrast Reverse Monogram colourway that I think ties in neatly to the autumnal palette going on. And yes, I’m a proponent of mixing black and brown.

In the case of the black in this outfit – in a past life, Taylor may have worn this dress with flat, knee high boots. Or sky high nude pumps. Or two tone brogues (maybe a cream and cognac brown combo?). But here we see a nod to todays trends with a heavy, black, chunky sole stomp-worthy boot. Proof of the power of styling and accessorizing to truly change a look completely.

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Toronto International Film Festival | Toronto, Canada | September 9, 2022

Louis Vuitton custom gown

For Taylor’s appearance at TIFF, I was hedging bets as to whether she would show up in the business babe-adjacent attire that she has favoured when attending promotional events where she wants to underscore her title as director on the project … or leaning into the glam showgirl aesthetic that tentatively appears to be the defining factor of the upcoming Midnights era.

In making her appearance at TIFF in this very glam sequinned custom LV gown: I think we have our answer.

I love how the gold paillettes are very reminiscent and recognizable within Taylor’s style repertoire. The girl has yet to meet a sequin she doesn’t love. But the very elegant way the skirt falls (perfectly hemmed btw to just kiss the floor – so well done) combined with the draping chain details makes this feel like a classed up extension of her MTV VMA appearance that had very similar shoulder details. It’s also a very nice slideshow moment where we now have a Midnights-esque appearance in: Silver, a colour, and now gold.

The RED hair (those bangs! the sleek blowout!) gave me temporary whiplash wondering if this was an appearance from 2012 I had somehow missed also feels like a very prescient tie-in to the fact that the project she is promoting is for that very same re-recorded album.

All in all – well done. She looks great, she looks classy, she looks glam and it somehow hits the mark for both of the albums she’s promoting (RED TV and Midnights). And that is not easy to do!

Worn with: Melis Goral earrings and Djula + Cadar rings

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

Louis Vuitton ‘Lingerie Inspired Cropped Tank Top’ – $875.00 (sold out)

Gosh! How much have I missed her? For real. It was so good to see Taylor up on stage again after so many years away. And also so fun to see her take to someone else’s stage and with significantly less pressure for her own setlist.

Now before we jump on the TS10 bandwagon I want to remind people that Taylor has an excellent history of being a good sport and adopting a friend’s on-stage aesthetic to #commit to the performance. See: Fifth Harmony on the 1989 Tour.

Especially because Haim are Louis Vuitton ambassadors and their tour looks were custom designed by LV.

Worn with: Louis Vuitton pants

Get the look: Puma, $27.00