Leaving a photoshoot for Target | New York City, NY | September 15, 2014
Aldo ‘Orphillia Ankle Boots’ – $110.00
Worn with: Aritzia top, Dolce & Gabbana bag and River Island shorts
Also worn: Arriving at her apartment September 24 and October 3
Critically Kind takes on Taylor's fashion
Leaving a photoshoot for Target | New York City, NY | September 15, 2014
Aldo ‘Orphillia Ankle Boots’ – $110.00
Worn with: Aritzia top, Dolce & Gabbana bag and River Island shorts
Also worn: Arriving at her apartment September 24 and October 3

Leaving her apartment | New York City, NY | November 12, 2014
Paige Denim ‘Skyline Skinny Jeans’ – sold out
Worn with: 525 America top and Rag & Bone booties
Also worn: Leaving her apartment March 30
Leaving her apartment | New York City, NY | November 12, 2014
Paige Denim ‘Skyline Skinny Jeans’ – sold out
Worn with: 525 America top and Rag & Bone booties
Also worn: Leaving her apartment March 30

Walking around Catalina (x) | Santa Catalina Island, CA | January 9, 2015
Rag & Bone ‘Dunaway Hat’ – $195.00
This one is kind of a shot in the dark post but due to Taylor’s love for the brand, this is my current best guess for the hat she wore while on vacation.
This particular hat features a cute tie feature of its band on one side so if any other photos emerge of Taylor in this outfit, I’m praying they reveal the other side of this hat.
Detail image is here.
Worn with: Free People dress
Click through for some alternative hat options:
Walking around Catalina (x) | Santa Catalina Island, CA | January 9, 2015
Rag & Bone ‘Dunaway Hat’ – $195.00
This one is kind of a shot in the dark post but due to Taylor’s love for the brand, this is my current best guess for the hat she wore while on vacation.
This particular hat features a cute tie feature of its band on one side so if any other photos emerge of Taylor in this outfit, I’m praying they reveal the other side of this hat.
Detail image is here.
Worn with: Free People dress
Click through for some alternative hat options:

On vacation | Santa Catalina Island, CA | January 9, 2015
Free People ‘Jen’s Pirate Booty: I Awoke Caftan’ – $268.00
If Taylor continues wearing things as enviably boho as this, she can stay on vacation for as long as she likes. I already feel like I’m lusting once again for her style to take a permanent swerve in this direction for the next era.
On vacation | Santa Catalina Island, CA | January 9, 2015
Free People ‘Jen’s Pirate Booty: I Awoke Caftan’ – $268.00
If Taylor continues wearing things as enviably boho as this, she can stay on vacation for as long as she likes. I already feel like I’m lusting once again for her style to take a permanent swerve in this direction for the next era.

Walking around Catalina (x) | Santa Catalina Island, CA | January 9, 2015
Free People ‘Dreamy Daze Print Dress’ – $128.00
Boho!Taylor is one of my favourite things and I’m so in love with this effortless outfit she wore while walking around with friends on Catalina. Of course, Taylor’s pick for boho chic items has always been Free People. Adding matching brown neutrals including a hat, belt and heeled ankle booties (!!!!) made the outfit that much more perfect.
Worn with: Rag & Bone hat
Walking around Catalina (x) | Santa Catalina Island, CA | January 9, 2015
Free People ‘Dreamy Daze Print Dress’ – $128.00
Boho!Taylor is one of my favourite things and I’m so in love with this effortless outfit she wore while walking around with friends on Catalina. Of course, Taylor’s pick for boho chic items has always been Free People. Adding matching brown neutrals including a hat, belt and heeled ankle booties (!!!!) made the outfit that much more perfect.
Worn with: Rag & Bone hat

Speak Now photocall | October 2010
Urban Outfitters ‘Toe Cap Oxford Shoe’ – no longer available
Taylor wore these suede and metallic oxfords by Deena & Ozzy (via retailer UO) for her Speak Now photocall.
Taylor also wore a red Trashy Diva dress in another shot from the photocall.