20+ Cute Chicago Outfit Ideas You Can’t Get Around This Year
IG: itsmrsbarclay
Chicago’s one of those cities where you need to be ready for… pretty much anything. I’ve been there in April and had sun, rain, and wind all in the same afternoon.
First trip, I didn’t pack a jacket and ended up panic-buying one near Millennium Park (best impulse purchase ever). The style here is practical but still fun – people know how to dress for the weather and still look good.
And yes, your shoes matter. You’ll walk more than you think, even if you’re mostly Ubering.
Here are my absolute favorite Chicago outfit ideas I’m completely obsessed with atm and I’m sure you’ll love them just as much as I do!
20+ Cute Chicago Outfit Ideas You’ll Love
Grey Pleated Skirt with Navy Blue Sweater
This grey pleated skirt with a navy sweater is so perfect for a fall day at the Art Institute of Chicago! I love how it’s preppy yet cozy for museum hopping. Pair with a structured tote and loafers.
Baggy Jeans with Grey Graphic Tee
You need these baggy jeans with a grey graphic tee for a casual Chicago coffee shop hangout! It’s so cool and comfy for sipping lattes in Wicker Park. Add a crossbody bag and sneakers.
Chicago Outfit with Black Shorts and White Top
Can we talk about these black shorts with a white top? They’re perfect for a summer stroll along the Chicago Riverwalk, feeling so breezy! I’d toss on a straw hat and slip-on sandals.
Black Mini Dress Chicago Outfit
Picture yourself in this black mini dress, hitting up a Chicago rooftop bar at night! You’ll feel like a total city star sipping cocktails. Pair with a bold red lip and strappy heels.
Denim Shorts with White Button-Down Shirt
This white button-down with denim shorts is so perfect for a Chicago street festival in the summer! I’m all about that fresh, laid-back energy. Pair with a fanny pack and canvas sneakers.
Cream Knit Sweater with White Mom Jeans
This cream knit sweater with white mom jeans is so cozy for a Chicago fall day at Lincoln Park Zoo! You’ll look cute and warm wandering around. Pair with a crossbody bag and ankle boots.
Brown Leather Jacket with Brown Joggers Outfit
Okay, this brown leather jacket with brown joggers is perfect for a Chicago evening at a jazz club! I’m loving how it’s edgy yet comfy for a night out. Pair with a small clutch and heeled boots.
Grey Mom Jeans with Black Longsleeve Look
These grey mom jeans with a black longsleeve are so perfect for a Chicago day exploring Logan Square’s murals! You’ll feel artsy and relaxed snapping pics. Pair with a small backpack and sneakers.
Navy Sweater with White Mom Jeans Outfit
You’ve gotta try this navy sweater with white mom jeans for a Chicago bookstore date! It’s so chic and cozy for browsing shelves. Pair with a structured tote and loafers for a bookish, city look.
Grey Wool Coat with Grey Jeans and White Top
This grey wool coat with grey jeans and a white top is so perfect for a chilly Chicago day at the Field Museum! I’m all about that sleek, wintery energy. Pair with a knit scarf and ankle boots.
Trench Coat with Mom Jeans and Black Top
Picture yourself in this trench coat with mom jeans and a black top, strolling through Millennium Park! Pair with a crossbody bag and heeled boots.
Cargo Blue Jeans with Brown Leather Jacket
These cargo blue jeans with a brown leather jacket are so perfect for a Chicago night at a blues bar! I love how it’s bold and ready for live music. Pair with a small clutch and ankle boots.
White Tube Top with Black Polka Dot Skirt
This white tube top with a black polka dot skirt is so cute for a Chicago summer rooftop brunch! You’ll feel flirty and fabulous sipping mimosas. Pair with a woven clutch and strappy sandals.
Khaki Cardigan with Blue Shorts Chicago Look
Can you even with this khaki cardigan and blue shorts? They’re perfect for a Chicago day at Navy Pier, munching on popcorn! I’d add a fanny pack and slip-on sneakers.
Beige Plaid Skirt with Teddy Jacket Outfit
This beige plaid skirt with a teddy jacket is so perfect for a cozy Chicago fall day at a farmers market! You’ll look cute and warm picking out pumpkins. Pair with a crossbody bag and flat boots.
Black Leather Jacket with Blue Mom Jeans
This black leather jacket with blue mom jeans is so perfect for a Chicago night out in River North! I’m all about that edgy, city energy. Pair with a small clutch and heeled boots.
Camel Trench Coat with Mom Jeans Chicago Outfit
Picture yourself in this camel trench coat with mom jeans, hitting up a Chicago art gallery! You’ll feel like a stylish local soaking in the culture. Pair with a crossbody bag and loafers.
Burgundy Leather Jacket with Denim Jeans
You’ve gotta try this burgundy leather jacket with denim jeans for a Chicago evening at a comedy club! It’s so bold and perfect for laughing the night away. Pair with a small tote and ankle boots.
FAQ:
What is the fashion style in Chicago?
It’s a mix – a little sporty, a little classic, with a hint of whatever’s trending. You’ll see puffer jackets in winter, flowy dresses in summer, and plenty of denim all year.
What is the 3-3-3 rule for clothes?
It’s basically packing three tops, three bottoms, and three pairs of shoes that all mix and match. Works great for a trip here so you’re not hauling your whole closet.
Is Chicago a dressy city?
Not really – unless you’re going somewhere fancy. Day-to-day is more casual, but people still look put-together. Dinner at a nice place? Yeah, you’ll want to step it up.
What to pack for 4 days in Chicago?
Layers. Always. A jacket, a couple sweaters or sweatshirts, jeans, a nicer outfit for dinner, and comfy shoes. If it’s winter, throw in gloves and a hat.
How should Chicago style look?
Weather-ready but not boring. Think a good coat, stylish sneakers or boots, and maybe one statement piece – like a bold scarf – to break up the neutrals.
What to wear to events in Chicago?
Depends on the event. Sports game? Hoodie and jeans. Theatre night? Dressier coat, boots, maybe a nice dress or smart trousers. Summer festivals? Light, breathable clothes you can move in.
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