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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.