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The 5 Shoes You Need to Survive Fall in Chicago

Neither rain nor snow nor poorly placed subway grates can stop these shoes. They’re stylish survivors, ready to take on whatever the city throws at you. In short, they’re the only five you need this fall.

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Block-Heel Hiker

For the urban wilderness (aka subway grates and mystery puddles), a style both practical and stylish. 

Get the look: ASOS ($60); Stuart Weitzman ($585); Gucci ($950)


Embellished Sneaker

Combine a little sparkle with laid-back comfort and you have the perfect casual Friday shoe.

Get the look: Steve Madden ($89); Ash ($185); Golden Goose ($665)

Free People

Brocade Slide

You need an edgier alternative to ballet flats, and this one feels like walking around in your bedroom slippers.

Get the look: Free People ($128); Tory Burch ($348); Manolo Blahnik ($645)

Rag & Bone

Stylish Rain boot

Oh hey, it’s raining for the umpteenth day in a row. At least you look chic.

Get the look: Barneys ($145); Loeffler Randall ($195); Rag & Bone ($225)

Neiman Marcus

V-Front Kitten Heel

Because we just can’t do another Saturday night in sky-high stilettos, and the V-front still elongates our legs….for days.

Get the look: Marc Fisher ($90); Ganni ($235); Balenciaga ($665)

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