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Out and about | New York City, NY | March 22, 2014

Rag & Bone ‘Newbury Bootie’ – $495.00

And that makes three! True to her form, when Taylor likes something – she really likes something. Taylor now owns these adorable, instantly-classic heeled ankle booties in dark brown, black and now ‘deep brown’.

Worn with: Urban Outfitters beanie, Dolce Vita coat, Red C Jewels ring, Dolce & Gabbana bag and Hudson Jeans pants

Check out the multiple colours Taylor owns these booties in here.

Which colour has been your favourite thus far?

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Out shopping in SoHo | New York City, NY | March 20, 2014

Rag & Bone ‘Newbury Bootie’ – $495.00

I’m so happy to see Taylor continuing to wear heeled ankle booties! And, in typical Taylor fashion, she also owns these same boots in two other colours.

Worn with: Ralph Lauren coat, Laura Gravestock necklace, Red C Jewels ring and Dolce & Gabbana bag

Check out the multiple colours Taylor owns these booties in here.

You can shop the look for under $40 here:

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Out shopping in SoHo | New York City, NY | March 20, 2014

Rag & Bone ‘Newbury Bootie’ – $495.00

I’m so happy to see Taylor continuing to wear heeled ankle booties! And, in typical Taylor fashion, she also owns these same boots in two other colours.

Worn with: Ralph Lauren coat, Laura Gravestock necklace, Red C Jewels ring and Dolce & Gabbana bag

Check out the multiple colours Taylor owns these booties in here.

You can shop the look for under $40 here:

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Arriving at LAX Airport | Los Angeles, CA | February 12, 2014

Rag & Bone ‘Harrow Leather Ankle Boots’ – $495.00

And here we have the debut candid appearance of Taylor’s new short hair! Looking inexplicably like the model who inspired her new ‘do – Karlie Kloss – Taylor wore this awesome pair of red heeled ankle booties.

If you’ve been a TSS follower the last few weeks you know that this shoe silhouette has been a favourite of mine so I’m happy to see it continue here.

Worn with: Ann Taylor top, Dolce & Gabbana bag and Taylor Guitars gig bag

Check out all the times Taylor has worn these boots here.

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Arriving at LAX Airport | Los Angeles, CA | February 12, 2014

Rag & Bone ‘Harrow Leather Ankle Boots’ – $495.00

And here we have the debut candid appearance of Taylor’s new short hair! Looking inexplicably like the model who inspired her new ‘do – Karlie Kloss – Taylor wore this awesome pair of red heeled ankle booties.

If you’ve been a TSS follower the last few weeks you know that this shoe silhouette has been a favourite of mine so I’m happy to see it continue here.

Worn with: Ann Taylor top, Dolce & Gabbana bag and Taylor Guitars gig bag

Check out all the times Taylor has worn these boots here.

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Arriving at LAX Airport | Los Angeles, CA | January 28, 2014

Rag & Bone ‘Newbury Bootie’ – $495.00

Worn with: Ray-Ban Wayfarers, Ralph Lauren turtleneck and Dolce & Gabbana bag

Taylor arrived at LAX Airport today, no doubt on her way to London as she begins the European Leg of the RED Tour this weekend at the O2 Arena. As for her clothes …

I sense a really exciting trend! This is the third pair of heeled ankle boots Taylor has worn within just the last month. The first two pairs being her Frye ‘Courtney’ lace up boots and this eyecatching red pair of Rag & Bone ‘Harrow’ boots.

I think the heel aspect brings a more chic, mature aspect to Taylor’s style that I much prefer over her vintage-y oxford flats, casual Keds sneakers or ladylike kitten heels.

Check out the multiple colours Taylor owns these booties in here.

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Arriving at LAX Airport | Los Angeles, CA | January 28, 2014

Rag & Bone ‘Newbury Bootie’ – $495.00

Worn with: Ray-Ban Wayfarers, Ralph Lauren turtleneck and Dolce & Gabbana bag

Taylor arrived at LAX Airport today, no doubt on her way to London as she begins the European Leg of the RED Tour this weekend at the O2 Arena. As for her clothes …

I sense a really exciting trend! This is the third pair of heeled ankle boots Taylor has worn within just the last month. The first two pairs being her Frye ‘Courtney’ lace up boots and this eyecatching red pair of Rag & Bone ‘Harrow’ boots.

I think the heel aspect brings a more chic, mature aspect to Taylor’s style that I much prefer over her vintage-y oxford flats, casual Keds sneakers or ladylike kitten heels.

Check out the multiple colours Taylor owns these booties in here.

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Out antique shopping | Los Angeles, CA | January 21, 2014

Rag & Bone ‘Harrow Leather Ankle Boots’ – $495.00

Worn with: Lanston tunic, Reformation skirt and Dolce & Gabbana bag

Check out all the times Taylor has worn these boots here.

GET THE LOOK: For under >$55.00

Just when I thought Taylor was absolutely losing her shoe game she comes out and knocks this candid outfit right out of the park. I’m so overwhelmed by how mature, chic and statuesque she looks here I’m a little teary-eyed.

Okay, yes, that was overdramatic. But I’m so in love with these candids. She looks so put together and I’m actually in love with the monochrome all-black look and the pop of red via her shoes and lips here. I can see Rosie Huntington-Whiteley wearing this outfit that’s how envious this street-style is.