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Arriving at Angelica Kitchen | New York City, NY | July 22, 2014

Christian Louboutin ‘Lady Peep Pumps’ – $945.00

Taylor hit the gym once again with model pal Karlie Kloss, hitting the streets in these sky-high heels. Who else could they be by but the master of the 6-inch: Christian Louboutin.

Her Frye ‘Maya’ pump would have made for a softer, more ladylike finish.

Worn with: Lulu Frost necklace, Reformation dress and Tod’s handbag

Also worn: Leaving her apartment, September 15

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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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Leaving the gym | New York City, NY | July 16, 2014

Rag & Bone ‘Newbury Bootie’ – $495.00

When Taylor first began her epic New York Fashion Takeover back in March, she kicked off strutting the NYC streets in the black version of these Rag & Bone booties.

Eventually, as the cooler months progressed she went on to wear them in two other shades. Back then, I know that I was one of the many supporters of this shoe silhouette (ankle booties being one of my personal favourite styles).

That being said, one of her many pairs of oxford heels would have been preferred over these (still very adorable) booties.

Worn with: Equipment dress and Dolce & Gabbana bag

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

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Leaving the gym | New York City, NY | July 16, 2014

Rag & Bone ‘Newbury Bootie’ – $495.00

When Taylor first began her epic New York Fashion Takeover back in March, she kicked off strutting the NYC streets in the black version of these Rag & Bone booties.

Eventually, as the cooler months progressed she went on to wear them in two other shades. Back then, I know that I was one of the many supporters of this shoe silhouette (ankle booties being one of my personal favourite styles).

That being said, one of her many pairs of oxford heels would have been preferred over these (still very adorable) booties.

Worn with: Equipment dress and Dolce & Gabbana bag

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

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Heading to Karlie Kloss’ apartment | New York City, NY | July 14, 2014

Prada ‘Leather Round Toe Pump’ – no longer available

A nude pair of her go-to Prada heels finished off Taylor’s outfit — and makes those legs somehow look even crazy longer!

Worn with: Theysken’s Theory top, Dolce & Gabbana bag and Black Orchid shorts

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