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

Free People ‘Patton Porkpie Hat’ – $58.00

Taylor left her apartment this morning with Karlie Kloss in tow to head to another modelFIT workout.

To accessorize, Taylor wore her fave porkpie hat from Free People. For some reason, I’m really digging the minimalist simpicity of this outfit.

Taylor also wore this hat (and shoes) in her recent Instagram posing in front of some wings artwork by artist Kelsey Montague.

Worn with: Dolce & Gabbana bag, J Brand shorts and Rag & Bone boots

Check out the multiple times Taylor has worn this hat here.

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

Free People ‘Patton Porkpie Hat’ – $58.00

Taylor left her apartment this morning with Karlie Kloss in tow to head to another modelFIT workout.

To accessorize, Taylor wore her fave porkpie hat from Free People. For some reason, I’m really digging the minimalist simpicity of this outfit.

Taylor also wore this hat (and shoes) in her recent Instagram posing in front of some wings artwork by artist Kelsey Montague.

Worn with: Dolce & Gabbana bag, J Brand shorts and Rag & Bone boots

Check out the multiple times Taylor has worn this hat here.

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Arriving at the gym | New York City, NY | July 18, 2014

Alice + Olivia ‘Vance Boatneck Boxy Raglan Top’ – $176.00 $106.60
Alice + Olivia ‘Blase Flare Skirt’ – $220.00

Taylor first wore this peachy outfit on Father’s Day before changing into a yellow floral Oscar de la Renta dress. And I’m so glad Taylor decided to rewear it as we didn’t get decent pictures on its first outing.

While at first glance it would sort of seem that the boxy fit of Taylor’s top makes her look like she’s drowning in fabric. But I actually feel like the looser silhouette creates a balance between the super short hemline of her skirt — softening the look.

I’m absolutely loving Taylor in pastels and her accessories here were spot on. Including that fresh white mani she’s sporting — the perfect finish to such a summery outfit.

Worn with: Anthropologie barettes, Tod’s bag and Jimmy Choo sandals

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Arriving at the gym | New York City, NY | July 18, 2014

Alice + Olivia ‘Vance Boatneck Boxy Raglan Top’ – $176.00 $106.60
Alice + Olivia ‘Blase Flare Skirt’ – $220.00

Taylor first wore this peachy outfit on Father’s Day before changing into a yellow floral Oscar de la Renta dress. And I’m so glad Taylor decided to rewear it as we didn’t get decent pictures on its first outing.

While at first glance it would sort of seem that the boxy fit of Taylor’s top makes her look like she’s drowning in fabric. But I actually feel like the looser silhouette creates a balance between the super short hemline of her skirt — softening the look.

I’m absolutely loving Taylor in pastels and her accessories here were spot on. Including that fresh white mani she’s sporting — the perfect finish to such a summery outfit.

Worn with: Anthropologie barettes, Tod’s bag and Jimmy Choo sandals