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.
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.
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).
Into the Millennium
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.
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).
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.