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Taylor Swift Style 2011-2018
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Dolphins vs Chiefs | Kansas City, MO | January 13, 2024

Christian Louboutin ‘Panaroot Dune Combat Boots’ - $1,395.00

Taylor kicking off sub-zero WAG fashion all bundled up. I have to say the foresight to opt for Louboutin combat boots here are a comfy and also on-colour theme choice to sandwich style her custom jacket.

Worn with: Kristin Juszczyk jacket and Manu bag

Get the look: Sam Edelman

Out and about | New York City, NY | January 9, 2024

Stella McCartney ‘Ribbed Recycled Cashmere Sweater Dress’ - $1,490.00

I’m never one to turn my nose up at any shade of green, but if I were to pick a favourite it would probably land closer in the realm of something like this rich evergreen for me.

There’s something about the colour combination here that despite the bag sticking out to me tonally feels very walk through a wintery forest. evermore vibes, if you will.

Looking in my own closet, I’m very excited to copy + paste this combination myself - necklace stack included.

Worn with: Stella McCartney coat, YSL bag, and Gucci boots

Get the look: Macy’s, $95.00

Photo by Gotham via Getty Images

Out and about | New York City, NY | December 21, 2023

Guest In Residence ‘Grizzly Bomber’ - $895.00

A great example of two mainstay patterns of late:

1. This is another copy + paste Taylor outfit for me (they’re usually easy to spot when defined by a neutral/black-filled palette and very good outerwear)
2. The revolt against pants continues.

Worn with: Manu Atelier bag and Christian Louboutin loafers

Get the look: ASOS, $140

Photo by Gotham via Getty Images

Out and about | New York City, NY | December 12, 2023

Gant ‘240 Mulberry Street Leather Trench’ - sold out

This leather trench retailed in very limited quantities as part of Gant’s FW2023 capsule launch so it’s sadly no longer available but it cut a very chic, fashun moment for Taylor that I loved seeing her boldly experiment with.

Worn with: Versace bag, Louis Vuitton + Cathy Waterman jewelry, and Stella McCartney boots

Get the look: Bardot, $270.15

Photo by Gotham via Getty Images

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

Anine Bing ‘Hilary Faux Fur Jacket’ - $650.00

Layering up against the NYC chill, rather than a long wool coat by the likes of recent outerwear favourites such as Gant - Taylor went glam in a faux fur shrug that, to me, once again just draws similarities to her Midnights Moschino Mayhem with Me moment.

Worn with: Clio Peppiatt dress, Messika earrings, Mazin Jewels necklace, Aquazzura bag and heels

Get the look: Abercrombie, $180.00

Photo by James Devaney via Getty Images

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

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

Out and about | Buenos Aires, Argentina | November 10, 2023

The Row ‘Zip Front Ankle Boots’ - $1,490.00

Worn with: Prada bag and Miu Miu skirt

Get the look: H&M, $99.00

Out and about | Buenos Aires, Argentina | November 10, 2023

Miu Miu ‘Pleated Check Mini Skirt’ - sold out

I am an ardent supporter of formula outfits and have definitely worn a combination of this ‘fit myself. I think this iteration with flat chunky boots with a shorter shaft height are a more balanced (and trendy) iteration of the black sandwich style + plaid mini skirt outfit than the last time we saw this combo on her.

If this particular skirt looks familiar to you it’s because Taylor liked it and so she got it in a different colour after wearing this in a plaid iteration just last week - another closet approach I am personally guilty of.

Worn with: Prada bag and The Row boots

Get the look: Urban Outfitters, $65.00

Out and about | New York City, NY | November 4, 2023

Miu Miu ‘Brown Plaid Skirt’ - $1,489.00

By item, this plaid pleated skirt is nothing new for Taylor’s style which has for years loved a “schoolgirl”-esque mini. By silhouette, however, the way this skirt hangs is more low waist then Taylor would normally opt for.

The effect feels very Rachel Green meets Regina George.

Worn with: Jacquie Aiche necklace + bracelet, Jacquie Aiche + Foundrae earrings, Mazin Jewels rings, Stella McCartney bag, and Stella McCartney boots

Get the look: H&M, $24.99

Photo by Getty

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

The Row ‘Eglitta Straight Leg Corduroy Pants’ - $990.00

Worn with: Gant sweater, Mansur Gavriel bag, and Sézane loafers

Get the look: Urban Outfitters, $49.99

Photo by Gotham ℅ Getty

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

Mansur Gavriel ’M Frame Box Bag’ - $895.00

In terms of recycling accessories, Taylor previously carried this bag back in May. Back then, she paired it with a fresh white eyelet set by Ralph Lauren and complementary minimalist brown sandals by Aeyde. It’s fun here to see her carry this bag again in a new season and see it work just as well with the fall-like palette of her outfit today.

Speaking of things we’ve seen before - if I had to guess, Taylor’s security guard in the background here is also carrying her very first Gant piece we saw last month - their cropped wool blazer jacket.

Worn with: Gant sweater, The Row pants, and Sézane loafers

Also worn: May 24, 2023

Get the look: Matt & Nat, $110.00

Photo by Gotham ℅ Getty

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

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

Prada ‘Leather Knee High Boots’ - $1,040.00

For anyone who would like to continue to deny the resurgence of 1989-era clothes, I present to you a pair of Prada boots not seen since January 1, 2015.

Between the two occasions we’ve seen these boots, I’m a much bigger fan of this iteration which feels far more pared back and - simply speaking - cooler.

Worn with: Stella McCartney shirt, Ralph Lauren hat, and Tod’s bag

Get the look: Journee Collection, $90.99

Also worn: January 1, 2015

“IT’S COOL” (x) | October 23, 2023

Reformation ‘Jadey Oversized V-Neck Sweater’ - $298.00

This brown tone feels very on trend for fall colour palettes these days and looks incredibly cozy.

Get the look: H&M, $29.99