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Out to dinner | Los Angeles, CA | October 19, 2023

Tod’s ‘Logo Plaque Leather Crossbody Bag’ – $2,525.00

While this may be Taylor’s second brown leather crossbody bag from Tod’s in the year 2023, what this brand will always bring me back to is the soft, curvy nude ‘Sella’ tote by Tod’s that Taylor carried relentlessly from April through July in 2014.

Worn with: H&M top, Anthropologie clip

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

Roger Vivier ‘Viv’ Choc Bag in Leather’ – $3,995.00

In terms of bag style, Taylor will typically opt for a cross-body worn on her right shoulder or a shoulder bag propped on the top of her forearm. So in an instance like this, it’s fun and notable to see her actually tote a shoulder bag where its name implies.

I do love the rich tones of this bag (the red speaks to me personally) but I wouldn’t have minded it in the black shade that it comes in.

Worn with: Maria Tash earrings, Alessandra Camilla Milano earrings, Jean Paul Gaultier top, Balenciaga corset, Khaite skirt, and Louis Vuitton boots

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Attending SNL after party | New York City, NY | October 14, 2023

Aupen ‘Nirvana Bag’ – $340.00

Taylor previously carried this braided bag at Jack Antonoff’s wedding. It does a great job of marrying the black and gold elements present through the rest of the ‘fit while also balancing the straighter lines of the bustier and slacks with the organic texture of its handle.

Worn with: Maria Tash earrings, Gant coat, Mazin Jewels necklace, Versace corset, and Greymer sandals

Also worn: Jack Antonoff’s wedding

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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 21, 2023

Brandon Blackwood ‘Kendrick Croc-Embossed Leather Top Handle Bag’ – $300.00

Given the pending release of 1989 (Taylor’s Version) and the full release of the tracklist this week, vault songs included, I find the name of this bag reasonably suspicious in the wake of the absence of a Taylor’s Version of the “Bad Blood” remix.

Worn with: Logan Hollowell necklace, Alaïa bodysuit, The Row belt, The Row pants, and Aquazzura sandals

Photo by Getty

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

Luana Italy ‘Paley Mini Pony Hair Satchel’ – $378.00 (no longer available)

I’ve talked about it a lot, but a distinctive feature of Taylor’s style is a masterful mix of designer pieces with accessible high street and smaller, indie designers thrown in. This particular bag – a stunning green one that I’ll put myself first in line for if she ever decides she has no need for it anymore – is incredibly interesting to me.

The brand Luana Italy was founded in the 60s by Giuseppe Rosadi and so named after his daughter, Luana, who would inherit the business and grow its signature top-handle designs over the span of decades. The brand was known for “femininity and cutting edge style with fresh yet timeless designs”. Due to slowing performance, the brand was acquired by 5M USA in 2013 with the goal of making a comeback. The CEO of 5M said at the time, “Luana was such an important brand in Italy back in the Seventies and Eighties that we wanted to revive its legacy.” Influential in the 80s? Colour me intrigued.

I provide this context because some time between 2019 and now, Luana fell out of business (they made a showing at Coterie Marketplace in February 2019). Yet somehow, Taylor still has one of their “impeccable, luxurious handbags” as per Eve Bender the VP of sales for 5M at the time of Luana Italy’s appearance at Coterie.

Its appearance now is fascinating to me, assuming that some time has passed between Taylor acquiring it and it making its street style debut. But that snake-like chain detail and overall colour plus its ties to the 80s and 2013 relaunch is catching my interest. A lot.

Worn with: EB Denim jacket, Reformation dress, and Reformation boots

Photo by Pap Culture

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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.

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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.