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

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

Despite the competing shades of brown, this is still such a great copy + paste fall ‘fit for me. The emblem knit layered over a crisp white button up is so preppy chic to me. And I love the combination of a “dress up” and “dress down” accessory factor via the competing laidback baseball cap and killer tall boots (which I’m so glad to see are having a fashion trend resurgence).

Worn with: Stella McCartney shirt, Ralph Lauren hat, and Prada boots

Also worn: October 19, 2023

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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 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.

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Rep Room | Pasadena, CA | May 19, 2018

Thanks @emmas-clothes!

Tod’s ‘Midi Lace Up Boots’ – $1,080.00 (sold out)

Not the shoe of choice I would pair with this lighter maxi dress, but perhaps with a tight leather skirt and blouse I could see this slaying. 

Worn with: BA&SH dress

Get the look:

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Rep Room | Pasadena, CA | May 19, 2018

Thanks @emmas-clothes!

Tod’s ‘Midi Lace Up Boots’ – $1,080.00 (sold out)

Not the shoe of choice I would pair with this lighter maxi dress, but perhaps with a tight leather skirt and blouse I could see this slaying. 

Worn with: BA&SH dress

Get the look:

!function(doc,s,id){ var e, p, cb; if(!doc.getElementById(id)) { e = doc.createElement(s); e.id = id; cb = new Date().getTime().toString(); p = ‘//shopsensewidget.shopstyle.com/widget-script.js?cb=1526876016375?cb=’ + cb; e.src = p; doc.body.appendChild(e); } if(typeof window.ss_shopsense === ‘object’){ if(doc.readyState === ‘complete’){ window.ss_shopsense.init(); } } }(document, ‘script’, ‘shopsensewidget-script’);

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Boarding a private plane w/ Tom Hiddleston | Watch Hill, RI | June 16, 2016

Tod’s ‘Studded Buckled Leather Sandals’ – $417.00

And the adventure continues. I’m desperately wishing we could get some HQ versions of these candids as, if you know me at all, it includes many of the things I love most. Grey, black, and ankle strap sandals. 

Let me know your thoughts over at @taylorswiftstylequestions.

Shop similars for under $100:

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Boarding a private plane w/ Tom Hiddleston | Watch Hill, RI | June 16, 2016

Tod’s ‘Studded Buckled Leather Sandals’ – $417.00

And the adventure continues. I’m desperately wishing we could get some HQ versions of these candids as, if you know me at all, it includes many of the things I love most. Grey, black, and ankle strap sandals. 

Let me know your thoughts over at @taylorswiftstylequestions.

Shop similars for under $100:

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Leaving Reese Witherspoon’s birthday party | Los Angeles, CA | March 20, 2016

Tod’s ‘Laser Cut Leather Ankle Boots’ – $398.00

These boots are basically my newest love. If you’ve been following TSS for awhile, you know I have a love for Taylor’s ankle boot collection. And these boots are no exception.

The heel shape, the buckle, and that cool laser cut detail? I’m all about these as a night out shoe.

Worn with: Isabel Marant top + skirt and Versace bag

Shoes like this can go with everything! Shop budget-friendly similars:

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