25+ Chicago Outfit Ideas + Inspo On What To Pack & Wear In Chicago

 

Hey there, fashion enthusiasts! If you’re planning your first trip to the Windy City and wondering what to pack, you are in the right place.

Having trotted around the USA and Europe, I’ve picked up a thing or two about dressing for city adventures. Chicago, with its vibrant culture, diverse activities, and unpredictable weather, offers a unique style challenge that I’m here to help you navigate.

 

 

Typical Chicago Style

Chicagoans have mastered the art of blending practicality with style. The city’s fashion is as diverse as its neighbourhoods, with a mix of upscale elegance and laid-back chic.

You’ll see a range of styles, from sophisticated coats in The Loop to artsy ensembles in Wicker Park. The key? Versatility and comfort stand up to the city’s bustling vibe.

 

 

Things To Consider When Packing For Chicago

• Weather Woes: Chicago’s weather can be a bit of a wildcard. Summers are warm and winters are cold, but the in-between seasons can fluctuate wildly. Layers are your best friend.
• City Exploration: You’ll likely do a lot of walking or hopping on and off the CTA, so comfortable footwear is a must.
• Activity Diversity: From brunch spots to jazz bars, theatre outings, and architectural tours, your wardrobe needs to cover a range of occasions.

 

 

 

 

Top 10 Chicago Outfit Ideas

 

Brunch in the City

Start with a comfy yet chic jumpsuit paired with low-block heels for easy walking. Accessorize with a crossbody bag for hands-free exploration. We have covered tips on the best brunch places in Chicago in additional inspiration on Chicago brunch outfits see our other post.

 

@danaberez

 

Chic Stripes and Shorts for Exploring

For a day of exploring the city, you can’t go wrong with a striped tank top paired with black high-waisted shorts. The outfit is effortlessly stylish and comfortable, making it ideal for walking around downtown or visiting museums.

The brown belt adds a touch of sophistication, and the matching brown sandals ensure you’re ready for a day on your feet. Accessorize with oversized sunglasses and a minimalist watch for a polished look.

This ensemble is perfect for a casual day out, whether you’re sightseeing or shopping on the Magnificent Mile.

 

 

Elegant in Monochrome for Brunch

Heading to a chic brunch spot? A black crop top paired with a high-waisted white skirt creates a stunning monochrome look. The belt adds a sleek detail that ties the outfit together.

Pair this with strappy black sandals and a woven tote bag for a touch of casual elegance. Don’t forget your black sunglasses to complete this sophisticated look.

This outfit is perfect for a brunch date or a casual meeting with friends at one of Chicago’s trendy cafes.

 

 

Architectural Tour Ready

Opt for breathable fabrics. A cotton tee, lightweight trousers, and comfortable sneakers make the perfect combo for walking tours. Don’t forget your sunglasses and a camera!

 

 

Theatre Elegance

A night out at the theatre calls for a bit of glam. A sleek midi dress with a statement jacket (think velvet or sequined) and heeled boots fit the bill perfectly.

 

 

 

Urban Edge for Casual Outings

For a casual outing with an urban edge, try a black crop top paired with camouflage cargo pants. Top it off with a black blazer for a touch of chic contrast.

This outfit is great for those cooler summer days when you’re roaming the city or grabbing a coffee. Pointed-toe boots and a baseball cap add a fashionable twist to this edgy look. It’s perfect for an afternoon of exploring the city or a casual lunch with friends.

 

 

Beachy Vibes by the Lake

When you’re planning to relax by Lake Michigan, a white maxi dress is a perfect choice. This dress is breezy and comfortable, ideal for a day at the beach or a lakeside picnic.

Pair it with woven sandals and a straw hat to keep the sun at bay. Minimalist jewelry and a small wicker bag complete this effortlessly chic look. This outfit is perfect for a relaxed day by the water or a casual stroll along the lakefront.

 

 

Bar Hopping Chic

Embrace Chicago’s nightlife with a cute little cocktail dress or for something different, some edgy leather pants, a stylish top, and ankle boots. Add a pop of colour with your accessories to stand out.

 

@danaberez

 

 

Art Institute Inspiration

Channel your inner artist with a boho midi skirt, a tucked-in blouse, and comfy flats or keep is simple but elegant with a little blazer and some shorts paired with flats. A tote bag will carry all your essentials, plus a little room for souvenirs.

 

 

 

Lakeshore Biking

 For a leisurely bike along Lake Michigan, wear some cute shorts or  sporty leggings, a breathable top, and sneakers. A lightweight windbreaker will keep you prepared for breezy conditions.

 

 

 

 

 

Colorful and Fun for Exploring

Brighten up your day with an orange two-piece set. The matching top and shorts are both fun and fashionable, making this outfit perfect for exploring the city or attending a summer festival.

Pair it with comfortable black sandals and a small crossbody bag for a look that’s both practical and stylish. This outfit is ideal for those who love to make a statement with bold colors and are ready to take on the city with confidence.

 

 

Classic White Dress for Dinner

A white midi dress is a timeless choice for a dinner date or an evening event. The simplicity of the dress is its charm, allowing you to accessorize with bold pieces like pink flats and a statement necklace.

A small clutch and delicate bracelets add just the right amount of sparkle. This look is elegant and perfect for a night out at one of Chicago’s upscale restaurants or a cocktail party.

 

 

Millennium Park Picnic

 Casual and cute is the way to go. High-waisted shorts, a flowy top, and sandals make for a relaxed yet Instagram-worthy outfit.

 

 

Minimalist Chic for a Museum Visit

A black tank top and a white midi skirt create a minimalist chic look that’s perfect for a museum visit. The simplicity of the outfit allows you to focus on the art while still looking stylish.

Black flat sandals and a small handbag complete the look, making it both comfortable and fashionable. This outfit is great for spending a day at the Art Institute of Chicago or any of the city’s other cultural hotspots.

 

 

Magnificent Mile Shopping

Prepare for a day of shopping with stretchy jeans, a comfortable yet fashionable tunic, and easy-to-remove shoes for those fitting room trials. For some additional inspiration Blake below wearing a long cardigan paired with wide-leg trousers.

 

 

Beachside Elegance for a Day by the Lake

For a serene day by Lake Michigan, this outfit perfectly captures the essence of beachside elegance. A navy blue smocked crop top paired with white linen pants creates a striking contrast that is both chic and comfortable. The smocked top provides a flattering fit, while the lightweight linen pants keep you cool and stylish.

Accessorize with a small woven bag, which adds a touch of texture and is perfect for carrying your essentials. Beige slide sandals complete the look, offering comfort and simplicity. A pair of oversized sunglasses protects your eyes from the sun and adds a touch of glamour. Finish off with some delicate jewelry, such as layered necklaces and bracelets, to add subtle elegance to your outfit.

This look is perfect for a relaxed day by the lake, whether you’re enjoying a picnic, taking a leisurely walk along the shore, or simply soaking in the beautiful views. It’s a versatile and fashionable choice that ensures you stay comfortable and stylish throughout the day.

 

 

Navy Pier Exploration

For a day at Navy Pier, keep it simple and stylish with denim shorts, a graphic tee, and comfortable walking shoes. A backpack keeps all your day-out essentials in check.

 

 

Bright and Breezy for Daytime Events

For daytime events or a casual outing, an orange maxi dress is a fantastic choice. The vibrant color is eye-catching and perfect for summer. Pair it with white sunglasses and a small black handbag for a trendy contrast.

Wedge sandals will keep you comfortable while adding a bit of height. This outfit is great for attending outdoor events, summer parties, or just enjoying a sunny day in the city.

 

 

Casual and Comfortable for Travel

When traveling, comfort is key. A loose-fitting shirt dress is perfect for this purpose. It’s stylish yet incredibly comfortable, making it ideal for flights or long drives.

Pair it with black slide sandals and keep accessories minimal with a simple bracelet and sunglasses. This outfit is perfect for travel days or when you just want to be comfortable while still looking put together.

 

 

Fine Dining Delight

Experience Chicago’s culinary scene in a chic, tailored blazer paired with dark jeans or trousers. A pair of loafers or sophisticated flats rounds out this dinner-ready look.

 

@thegraydetails

 

Remember, visiting Chicago is all about embracing the city’s energy and diversity, and your wardrobe should reflect that.

Mix and match these ideas to create outfits that not only look great but also let you experience all that Chicago has to offer comfortably and stylishly. 

 

 

 

What To Wear In Chicago In Spring Summer Winter And Fall

Diving into the seasonal nuances of Chicago will ensure you’re well-prepared for its capricious weather patterns. Here’s how to pack smartly for each season in Chicago:

 

Spring In Chicago

Spring in Chicago can be unpredictable, with chilly mornings that blossom into warm afternoons. Layering is your best strategy.

Start with breathable basics like cotton tees or blouses and layer up with a light sweater or cardigan. A waterproof jacket or a chic trench coat is essential for those sudden spring showers.

Footwear should be versatile – think waterproof boots or comfortable sneakers that can handle a bit of rain. Don’t forget accessories like a lightweight scarf and an umbrella to navigate through the city’s spring whimsy.

 

 

Summer In Chicago

Summers in Chicago are glorious and warm, perfect for exploring the city’s outdoor attractions. Pack light and airy clothing – sundresses, shorts, and breathable tops will keep you cool while you’re out and about.

Sandals and comfortable walking shoes are a must for strolling along the Magnificent Mile or the lakefront. Sunglasses, a wide-brimmed hat, and sunscreen are crucial to protect you from the midday sun. And always carry a reusable water bottle to stay hydrated as you soak in the summer vibes.

 

 

Winter In Chicgo

Bracing for a Chicago winter means gearing up for cold and wind. Start with thermal underwear and layer up with fleece-lined leggings or pants, knit dresses, sweaters, and a heavy-duty down jacket designed to withstand the Windy City’s gusts.

Waterproof boots with good insulation are essential to keep your feet warm and dry, especially with Chicago’s snowy sidewalks. Don’t forget accessories like a warm hat, gloves, and a scarf to protect against the chill. A portable charger can be a lifesaver, as batteries tend to drain faster in cold weather.

 

 

 

Fall In Chicago

Fall in Chicago is a beautiful medley of crisp air and changing leaves, but temperatures can vary. Packing should focus on versatility – think jeans, long-sleeve tops, and light sweaters that you can layer under a medium-weight jacket. Comfortable footwear is key for walking through the city’s parks and along its picturesque streets.

A scarf and a beanie will add warmth as the temperatures drop in the evening. Given the chance of rain, a water-resistant jacket and umbrella should also make their way into your luggage.

No matter the season, always leave a little room in your suitcase for the inevitable treasures you’ll find in Chicago’s boutiques and markets. With these packing tips, you’ll be ready to embrace the Windy City in style and comfort, making the most of your visit regardless of the weather.

 

 

There you have it, a run down of tips on how to pack for Chicago as well as ideas on outfits to wear in Chicago.  Hope you enjoy your trip.