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Ajah, 28, accessorizes her dress from Housing Works with vintage boots from East Village shop Metropolis. Jonathan Baskin

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Nina, 21, is a model citizen, owning the trend by belting her thrift store romper and pairing it with Frye boots.Barneys creative director Simon Doonan approves: “During the punk era I used to wear leather shorts and engineer boots,” he says. “I like a heavy boot with a pair of shorts. And you have to have great legs, which fortunately I did. And still do!” Jonathan Baskin

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Molly wears vintage granny boots with knee-highs, cut off shorts, an Alexander Wang tank under a mesh tank from What Goes Around Comes Around and a Ksubi denim vest. Elizabeth Lippman

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Tess, a student, maneuvers the concrete jungle in a utilitarian look of All Saints combat boots, high-waisted shorts from Forever 21 and an Adam tank. Elizabeth Lippman

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7 For All Mankind’s “Olivia” boot ($360 at shopbop.com) works with miniskirts, dresses and shorts. Jonathan Baskin

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Military camo is one of fall’s must-have trends: “Dampa” boot, $1,112 at Isabel Marant, 469 Broome St. Jonathan Baskin

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Toughen up your floral frock with this studded motorcycle boot by Ash ($295 at shopbop.com). Jonathan Baskin

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Daniblack’s “Lilette” pair ($275 at endless.com) will go with just about everything. Jonathan Baskin

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