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Arriving at the gym | New York City, NY | July 21, 2014

Rag & Bone ‘Miles Boot’ – $550.00

I know there have been a lot of mixed feelings about Taylor’s latest affinity for pairing shorts with chunky heeled ankle booties. But what I think it boils down to is appropriate styling to pull the look off.

Here, with the simplicity (and quirk) of her high-waisted shorts with a white burnout tee and a porkpie hat, the boots don’t look as out of place.

Worn with: Free People hat, Dolce & Gabbana bag and J Brand shorts

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

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Arriving at the gym | New York City, NY | July 21, 2014

Rag & Bone ‘Miles Boot’ – $550.00

I know there have been a lot of mixed feelings about Taylor’s latest affinity for pairing shorts with chunky heeled ankle booties. But what I think it boils down to is appropriate styling to pull the look off.

Here, with the simplicity (and quirk) of her high-waisted shorts with a white burnout tee and a porkpie hat, the boots don’t look as out of place.

Worn with: Free People hat, Dolce & Gabbana bag and J Brand shorts

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

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Out and about | New York City, NY | April 29, 2014

Rag & Bone ‘Miles Boot’ – $550.00

Taylor’s chunky-heeled ankle booties were also by Rag & Bone and are a nice, refreshing change of pace from the heeled oxfords she’s been sporting over the last two weeks. They provide a much edgier, urban silhouette.

Worn with: Rag & Bone hat, DemyLee top and Dolce & Gabbana bag

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

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Out and about | New York City, NY | April 29, 2014

Rag & Bone ‘Miles Boot’ – $550.00

Taylor’s chunky-heeled ankle booties were also by Rag & Bone and are a nice, refreshing change of pace from the heeled oxfords she’s been sporting over the last two weeks. They provide a much edgier, urban silhouette.

Worn with: Rag & Bone hat, DemyLee top and Dolce & Gabbana bag

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