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Critically Kind takes on Taylor's fashion

jonasbrotha replied to your photo: 41st Annual Songwriters Hall of Fame | June 17,…
what are the sentimental reasons
Taylor wore that dress when she won the Hal David Starlight award which John Mayer presented to her. You can listen to bits of his speech here, including the line where he describes them both as “black swans” which is my OTP tag for John and Taylor on my personal blog.

41st Annual Songwriters Hall of Fame | New York City, NY | June 17, 2010
J. Mendel Spring 2010 RTW
I’ve mentioned before that this is one of my all-time favourite looks Taylor’s worn because of sentimental reasons. But I’ve never actually formally identified it.
Although it doesn’t look like it since Taylor’s version is this pretty lilac colour, her delicately draped frock is from one of her favourite designer’s spring line.
Worn with: Lorraine Schwartz jewelry and Christian Louboutin heels

Performing free concert | Central Park, NY | October 25, 2010
Cole Haan ‘Air Oleanna Boot’ – no longer available
Worn with: Alice + Olivia blouse and Paige Denim pants

Us Weekly | October 2008
Marchesa Spring 2008 RTW
This week some brand new behind-the-scenes shots from Taylor’s Us Weekly shoot with Hilary Duff and Lauren Conrad got released. I was feeling reminiscent and dug up this gorgeous Marchesa gown from Taylor’s style archive.
Marchesa’s flowing, ethereal, feminine style fits Taylor perfectly doesn’t it?

“Safe & Sound” music video | February 2012
Vintage dress
Taylor herself confirmed the beautifully haunting white chiffon dress she wore in the “Safe & Sound” music video is a 1920s vintage piece.

At the Kennedy Compound | Cape Cod, MA | August 2012
Club Monaco ‘Mary Intarsia Sweater’ – sold out
Well this is an interesting turn of events. Taylor’s usually a serial accessories repeater but it appears that she can’t let go of churning out this sweater when she’s feeling nautical. Here, Taylor wears it in Cape Cod as she goes sailboating with the Kennedy family.
Worn with: Joe’s Jeans shorts, Coach bag and Ray Ban sunglasses
Also worn: At Sydney Harbour
Get the look for less:

At the Kennedy Compound | Cape Cod, MS | August 2012
Joe’s Jeans ‘55 Colours Shorts in Atlantic’ – no longer available
Taylor already has a habit of purchasing a single item in multiple colours (see: her Ralph Lauren cable knit sweater addiction). This summer, I’m sensing an oncoming trend of Taylor actually trying to purchase every single one of Joe’s 55 colour shorts.
Worn with: Club Monaco sweater, Coach bag and Ray Ban sunglasses
Check out the multiple colours Taylor owns these shorts in here.

“Mine” music video | August 31, 2010
Lulu’s ‘Gardener’s Niece Dress’ – no longer available
This photo was taken from behind-the-scenes while Taylor was walking around the set of the music video. She wore this dress during the opening scene as she walked into the café to meet Toby.

Parade magazine | October 2010
Golden Goose ‘Camel Used Optic Boots Pony’ – no longer available
… But then stylists throw in a pair of designer boots to balance things out. These did once retail for about $1000 (USD/CAD).
Worn with: Urban Outfitters tank top