Brooklyn, N.Y.

Since you're likely to be out and about, these faux leather ponte leggings are the perfect item to take you from day to night and make you look oh-so-chic when paired with these statement heels and coat. Top with a classic shirt and sweater to balance things out.
To buy:
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J.Crew shirt, $88
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J.Crew sweater, $118
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Gap coat, $168
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Anthropologie heels, $138
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Michael Kors leggings, $100
London

You’ll feel beautiful, warm and ready to take in the sights in this cozy sweater dress and oversized scarf. Add a belt for some shape and structure and a leather skirt if you want to use the dress more like a cardigan.
To buy:
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Aritzia Sweater, $165
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Madewell fedora, $68
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Aritzia scarf, $65
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H&M faux-leather skirt, $129
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J. Crew Factory belt, $25
Disney World

Keep things cute and unfussy in a trendy jumpsuit paired with mocks and a denim jacket. For an easy catchall, try a fun tote that everyone can take turns carrying!
To buy:
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H&M jumpsuit, $30
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Gap jean jacket, $70
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Etsy bead necklace, $40
Montana

A graphic poncho, relaxed jeans and booties are perfect for a Thanksgiving feast in the heartland. They're also functional enough to wear on a trail walk, a leisurely horseback ride or during a fireside chat.
To buy:
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Madewell necklace, $58
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Madewell blouse, $70
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Zara jeans, $80
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Zara ankle boot, $100
SoCal

Brave the autumn heat while looking California cool in these faux leather shorts. A tissue-weight turtleneck and cool faux-fur vest add a touch of glamour, while pretty oxfords and a functional tote pull everything together.
To buy:
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J. Crew turtleneck, $30
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H&M faux-fur vest, $70
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Nordstrom tote, $48
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Zara shoes, $50
Texas

Ooze Southern charm in this playful tulle midi-skirt and pom-pom sweater. Pair with nude pumps for legs that don’t end.
To buy:
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C. Wonder bracelet, $58
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Nordstrom Nixon watch, $95;
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Anthropologie midi-skirt, $168
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Mango nude pump, $100
The Pacific Northwest

You’ll welcome the rain if it means wearing these stylish ankle wellies. Pair with a plaid blazer and flattering distressed jean to create that hipster vibe the Seattle area is famous for.
To buy:
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Madewell jeans, $135
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Boden coat, $228
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ASOS necklace, $11
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Zara blouse, $60
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Madewell boots, $195