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Taylor Swift Style 2011-2018
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Out and about | New York City, NY | October 27, 2023

Gianvito Rossi ‘Ankle Boots’ - $1,220.00 $850.00

Lovingly, it is never truly a fully 'Taylor’ outfit without an element of quirk or something slightly 'off’ to make it interesting and 'her’. I perhaps would have gone with this pair of boots in black, but Taylor opted for another rich colour to add to the palette of the outfit.

Worn with: Madewell blazer, Jacquie Aiche earrings + Foundrae necklace charm, Mazin Jewelry necklace + Foundrae chain, Hunting Season bag, and Acne Studios skirt

Photo by Getty

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

After Kansas City Chiefs v L.A. Chargers | Kansas City, MO | October 22, 2023

Nike ‘Air Force 1 Low By You’ - $135.00

Based on the unique grey label and gum sole, it appears that Taylor’s Nike sneakers are a custom pair using the brand’s “By You” feature. Hers look to be all white with the only customization being a 'Sport Red’ on the 'Swoosh / Backtab’ feature.

Worn with: Rally House tee

At Arrowhead Stadium | Kansas City, MO | October 22, 2023

Reformation ‘Lolita Platform Loafer’ - $348.00

Based on Taylor’s longtime love of the brand, my best guess from photos is Taylor’s platform loafers are these by Reformation.

The combination of a pleated skirt and a heeled loafer bring me back to Speak Now days for Taylor - it’s a youthful leaning fashion combination for Taylor that feels core to her feminine style and I love here that there’s an athletic twist to her tried and true schoolgirl style.

Worn with: Ellie Mae sweatshirt, Cartier necklace, Foundrae bracelet, and Jacquie Aiche bracelets

Get the look: Sam Edelman, $140

Out and about | New York City, NY | October 14, 2023

Greymer Spring/Summer 2014 sandals - no longer available

If you have ever thought: Surely Taylor doesn’t always consider what she wears and the messaging behind it. This post is for you.

Now defunct, Greymer is an Italian brand established in 1980. More importantly, the shoes Taylor is wearing here are from their Spring/Summer 2014 collection. When the entirety of the fashion world is at your disposal, why wear a pair of shoes from nearly a decade ago that so happens to nod to the year your upcoming re-record was originally released in?

Fashion history aside, I loved how the metallic heel of these sandals continued the gold hardware present through the rest of the outfit (necklace, corset straps, bag).

Worn with: Maria Tash earrings, Gant coat, Mazin Jewels necklace, Versace corset, and Aupen bag

Get the look: Michael Kors, $155.00

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

At Arrowhead Stadium | Kansas City, MO | October 12, 2023

Prada ‘Black Lace Up 110 Military Boots’ - $1,205.00

Despite not having HQ images of Taylor’s full ensemble (which I’d love!), I still feel reasonably confident on these boots which I suspect are an older pair by Prada that Taylor previously wore in September 2019 while on stage during her City of Lover concert.

Worn with: WEAR by Erin Andrews jacket and Balenciaga corset

Also worn: City of Lover concert

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

Giuseppe Zanotti ‘Intriigo Strap Sandals’ - $950.00

As a lover of a minimalist ankle strap sandal, my eye happily went to this pair of Giuseppe Zanotti heels. While I do personally love a tonal moment, looking at the lewk as a whole, I also can totally picture a champagne or silver pair of heels to complement her tennis jewelry and finish the ‘fit off on a brighter, complementary shimmery note.

Worn with: Oscar de la Renta gown, Cartier necklace + Anabela Chan bracelets, and Cartier studs + Cathy Waterman + Akillis + Anabela Chan rings

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

New Balance x Ganni ‘1906R Sneakers’ - $349.00

Worn with: Still Here hat, Free People shirt, Louis Vuitton bag, and Free People socks

At MetLife Stadium | East Rutherford, NJ | October 1, 2023

Christian Louboutin ‘Pumppie Botta Leather Knee-High Boots’ - $1,795.00

Worn with: Gant jacket, Logan Hollowell necklace, and Area shorts

Also worn: September 18, 2023

Get the look: Steve Madden, $169.95

At Arrowhead Stadium | Kansas City, MO | September 24, 2023

New Balance ‘550 Sneakers’ - $197.00

I respect that Taylor is the type of girl who will seize at any chance for an opportunity to wear a colour coordinated outfit.

Worn with: Ralph Lauren hat, New Era jacket, Jacquie Aiche earring, Dôen top, Louis Vuitton bag, and Ksubi shorts

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

Aquazzura ‘Twist 95 Pleated Sandals’ - $795.00

Calling this one another immediate copy + paste outfit for me. On a personal level, this is the kind of colour palette and style I feel most drawn to. Chic neutrals in smart silhouettes with pops of moody tones like burgundy. Plus some gold jewelry to accessorize. Yes!

Worn with: Logan Hollowell necklace, Brandon Blackwood bag, Alaïa bodysuit, The Row belt, and The Row pants

Get the look: Alohas, $122.00

Photo by Getty

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

Reformation ‘Nylah Nappa Knee Boot’ - $448.00

When you’re perfectly fine over this course of events.

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

Get the look: Target, $99.99

Photo by Pap Culture

Out and about | New York City, NY | September 18, 2023

Vince ‘Houndstooth Wool Blend Coat’ - $845.00
Cartier ‘Agrafe Herringbone Twisted Necklace’ - $27,250.00
Versace 'Greca Goddess Medium Leather Top-Handle Bag’ - $2,650.00
Christian Louboutin 'Pumppie Botta Leather Knee-High Boots’ - $1,795.00

Watching people excel in their given field is always a pleasure and a joy to watch. It’s how I feel seeing Taylor dancing with abandon at awards shows or singing to sold out stadiums of 70,000 people. But it’s also how I feel when I see her step out in fall attire in NYC. What a thrill! She’s always had a special knack for layers and colour palettes, but Taylor really does kill fall dressing. So much so that this latest string of outfits has been a consistent, “Yes I will copy + paste that onto my body” response from me. I’m just a sucker for a good piece of outerwear and an outfit dominated by black.

Speaking of black, two notes on her black accessories here.

Choice of brand is always something that comes to my mind, even when we see Taylor out and about in her daily life. Seeing her wear Versace immediately brings to my mind not only the recent memories of her outing at the MTV VMAs just last week (in classic black and gold Versace) but also me of Versace’s top tier placement in the Eras Tour setlist as part of her opening set. It’s subtle, of course, but I can see how even that simple evocation over into her street style would be a great way to keep top of mind her huge award show sweep and that she’ll be back on her record-breaking global stadium tour in less than two months. The bag itself has such a dreamy shape - love the curves.

The boots, on the other hand, immediately had me do a double take because they are incredibly similar to the 'Babel’ Louboutins she would wear so often in her early years. Given Taylor’s propensity lately for going back into her clothing archives, that really would have given me a shock. But no, this pair differs by a slightly different heel and a side zip.

Out to dinner w/ Blake Lively | New York City, NY | September 16, 2023

Tod’s ‘Leather Crossbody Mini Bag’ - $1,825.00
Foundrae 'Petite Chubby Ear Hoop’ - $1,570.00
& Other Stories ‘Leather Knee Boots’ - £145.00 (no longer available)

Taylor continues her social streak in NYC, heading out to dinner with Blake Lively at a members only club wearing a neutrals-dominated outfit (my favourite kind). A few people asked me how I felt about the combination of a cropped black cardigan, slate grey mini skirt, and burgundy boots. To which I say: Yes. This is definitely an outfit I’d personally wear.

But what’s so fun about it is that the idea of a pleated skirt and boot combination is not new to Taylor’s style. She’s been wearing some iteration of this pairing ever since she was a teen. What’s fun to watch is how she makes slight styling adjustments to make it more current and also more 'her’ of today. It’s that blend of familiarity but modernity that I feel is so relatable to Taylor’s style and what makes her feel so approachable and real, but also recognizable for those who have been observing her 'fits change from era to era. She’s always there underneath at all!

That aside, these particular boots actually have a story within Taylor’s fashion history. They first debuted in November 2014 and haven’t been seen since winter 2015. With 1989 (TV) around the corner, this obviously has my brows raised. If intentional, what a throwback.

The Tod’s bag is one she also wore earlier this year with a vintage NYU sweater.

On the jewelry front, this particular style from Foundrae (a brand she’s been loving as of late in her pursuit of the perfect stack) does come in a cute initial version which would be very up Taylor’s alley (she loves initial jewelry). However, given that she owns and has worn the matching necklace of the pictured style, this is the one I’m going with for now.

To see all the times Taylor has worn these boots, click here.