Channel your inner Carrie Bradshaw.
theSkimm

October 1, 2025

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Just Wear This

Nothing makes an outfit quite like a great pair of shoes. These are the trendiest — yet most wearable — styles we could find. Consider them auto-approved by your coolest friend.

The Tall Boots

 
 
Steve Madden Riggs Black Leather Boots

Steve Madden Riggs Black Leather Boots

Riding boots are big this season, but they’ll outlast trend cycles. 

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Wear them with…

The Tall Boots outfit

Check out the full outfit breakdown here.

The Ankle Boots

 
 
Sam Edelman Paige Ankle Boot

Sam Edelman Paige Ankle Boot

Your go-to booties, majorly upgraded. 

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Wear them with…

The Ankle Boots outfit

Check out the full outfit breakdown here.

The Loafers

 
 
Franco Sarto Alora Penny Loafer

Franco Sarto Alora Penny Loafer 

Penny loafers are in. Carolyn Bessette-Kennedy would wear these.

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Wear them with...

The Loafers outfit

Check out the full outfit breakdown here.

The Sneakers

 
 
Dolce Vita Serina Sneakers

Dolce Vita Serina Sneakers

What’s old is new again, including gum-soled, ‘70s-esque sneakers.

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Wear them with…

The Sneakers outfit

Check out the full outfit breakdown here.

The Ballet Flats

 
 
Madewell The Greta Ballet Flat

Madewell The Greta Ballet Flat

The most comfortable flats we’ve ever worn. 

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Wear them with...

The Ballet Flats outfit

Check out the full outfit breakdown here.

The Clogs

 
 
Seychelles New Routine Mule

Seychelles New Routine Mule

A good dupe for the Row’s $1,000+ clogs.

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Wear them with...