What to Pack Series

What to Pack: Chicago

Posted by Bee Shapiro on September 23, 2013 at 1:52:20 PM EDT | Post a Comment

Whether you go for the food, the shopping, the sports, or just for a good, old fashioned city break, Chicago offers something for everyone. President Obama's old stomping grounds are brutally brisk come winter, but the fall is the perfect time to grab a scarf and explore the Windy City. Pack these cool kid clothes and hit the town.

Women

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Magnificent Mile Days

Shop till you drop is the name of the game on Chicago's Magnificent Mile, lined with shops big and small. For a day of browsing the racks, start with this plaid poplin top ($450), which offers equal parts fashion and comfort.

Layer like a pro with this gray mixed yarn sweater on top for chillier days ($68).

Footwear should be easy to walk in without skimping on style. These metallic silver oxfords are a fun take on the metallic trend ($258).

The temps in October usually hover in the 60s, but the sun still shines bright. These tortoiseshell sunglasses will offer the right protection ($195).

Simple shapes travel well, like this tote in blue ($179.95). Plus, the pebbled leather will hold up better than, say, a smooth lambskin, hiding scratches and wear and tear.

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Nighttime Sizzle

A confessed gourmand? This city has a red-hot dining scene. Try to snag a coveted seat at Alinea, where chef Grant Achatz offers epic tasting menus that use wildly fun molecular gastronomy techniques. Dress for the occasion in a burgundy and black color-block dress ($82).

(Can't score a reservation? MK Chicago is more under the radar but also excellent.)

Especially for fall, a pointy high-heeled bootie (this style in black pony by Nine West, $149) gives any look a polished feel.

Pair those heels with black skinny pants, here accented with neat zips ($79.90).

A solid trench coat provides the right amount of coverage and warmth for breezier evenings ($169).

Finish it all off with a pair of silver hoops in an oversize shape for a touch of nighttime drama ($64).

Men

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Into the Millennium

The impressively futuristic Millennium Park is worth exploring for the architecture and one of its many events. Take a gander wearing these handsome boots ($150).

A straight fit jean, here in a vibrant deep blue, are fashion-forward enough for exploring Chicago's chic streets, while still maintaining a basic and simple look ($200).

On top, a maroon henley ($95) keeps the cool colors going while staying super comfy.

Or on sunnier days, pick this broken-in pocket tee ($24.50) for a rakish, no-effort look.

Cinch the look with waxed leather belt ($170) that's not too precious.

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Deep Dive

Don't ask a New Yorker, but Chicagoans know their way around a slice. The city is famous for its deep dish pizza, so give it a taste at Lou Malnati's for a casual night out. Throw on darker colored chinos (to hide any dribbling pizza sauce) like this olive-brown pair ($158).

After dinner, head to newish watering hole the Trenchermen for a Green Hornet cocktail made of gin, celery, and tonic. You'll fit right in wearing this long sleeved blue striped tee ($60).

Layer up for chillier nights by adding texture to the t-shirt, with this nubby gray sweater ($268.33)

Or pack a red tartan plaid shirt ($79.50) that will make for a smooth segue into the cooler months.

And in a nod to Chicagoans' undying love of baseball, this baseball jacket with leather sleeves is chic, sporty, and will let you fit right in with the local crowd ($450).

Photo Credits: Women Day: Courtesy of Kirna Zabete; J.CREW; COLE HAAN; www.stitchchicago.com; Topshop. Women Night: Courtesy of Nordstrom, Inc.; Nine West; ZARA; ZAPPOS.COM OR ITS AFFILIATES; TOMMY HILFIGER LICENSING, LLC. Men Day: Courtesy of Need Supply Company; J.CREW; Nordstrom, Inc.; Contextclothing.com and Fos5.com; G-STAR RAW. Men Night: Courtesy of 9 TENANTS, LLC; Club Monaco Corp.; Club Monaco Corp.; asos.com Ltd; Arrow and Arrow.

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