The Haute Seeker

What to Wear in Chicago: An Easy Outfit Guide For Every Season

Chicago, the Windy City, is renowned for its vibrant culture, stunning architecture, and diverse neighborhoods. Whether you’re planning a weekend getaway or an extended stay, it’s essential to pack the right outfits to stay comfortable and stylish throughout your trip. 

In this blog post, I’ll break down what to wear in Chicago for each season, offering insights into the local weather and wardrobe suggestions. 

Whether you’re exploring the Magnificent Mile or indulging in Chicago-style deep-dish pizza, this guide will have you covered.

What Clothes to Wear in Chicago?

Fall: A Symphony of Colors

Chicago’s fall is a visual feast for the senses, with leaves turning vibrant shades of red, orange, and gold. The weather is crisp, making it the perfect time for outdoor adventures.

Fall in Chicago typically brings mild temperatures ranging from the mid-50s to low 70s°F (13-23°C). To stay cozy and chic, layering is key. 

Start with a lightweight sweater or flannel shirt paired with jeans or comfortable leggings. Don’t forget a stylish jacket or trench coat for those cooler evenings. Complete your look with ankle boots and a versatile scarf that can double as an accessory.

You can rock this look to any event and stand out. Looking for things to do during the fall? Check out these 11 Chicago Fall Festivals to Look Forward to.

Winter: Embrace the Cold with Elegance

Chicago winters are legendary for their cold temperatures and occasional snowstorms. However, with the right clothing, you can still enjoy the city’s winter wonderland.

Chicago’s winter temperatures often hover in the 20s to 30s°F (-6 to -1°C), and the city experiences snowfall, creating a picturesque scene. 

To stay warm and stylish, opt for a cozy wool coat, insulated gloves, and a fashionable knit hat. Layer a turtleneck sweater under a thermal-lined jacket for added warmth. 

When it comes to bottoms, choose thermal leggings or fleece-lined jeans to keep the cold at bay. Waterproof boots with good traction are essential to navigate icy sidewalks.

For shopping in Chicago, check out boutiques like Akira and Ikram for winter essentials that combine fashion and function.

Spring: Blooms and Breezes

As winter bids adieu, Chicago springs to life with budding flowers and milder temperatures. Spring is a delightful season to explore the city’s parks and cultural attractions.

Spring in Chicago ranges from the 40s to 60s°F (4-20°C), with occasional rain showers. 

To make the most of your springtime visit, opt for a light raincoat or trench, which can be layered over sweaters or blouses. Pair these with slim-fit jeans or a skirt. Don’t forget comfortable walking shoes, as you’ll want to explore the city’s various beautiful neighborhoods on foot.

While shopping in Chicago, visit local gems like Eskell for trendy spring attire that supports women-owned businesses.

Summer: Sizzling Style

Summer in Chicago is a time for festivals, beach days, and exploring the city’s vibrant culinary scene. Expect warm weather and plenty of sunshine.

Chicago’s summer temperatures soar into the 70s and 80s°F (21-32°C), making it the perfect season for dresses, shorts, and lightweight tops. 

A sunhat and sunglasses are essential for protecting yourself from the sun’s rays. Don’t forget comfortable sandals or espadrilles for those long walks along Lake Michigan’s shoreline.

When shopping in Chicago for your summer wardrobe, consider supporting Black-owned boutiques like Kiwi’s Boutique, which offers a curated selection of dresses, outerwear, and jumpsuits.


What else we’re reading

Conclusion: Shop Now and Embrace Chicago’s Style

Now that you’re well-equipped with seasonal style tips for your Chicago adventure, it’s time to shop for the perfect wardrobe. 

Whether you’re chasing the fall foliage, braving the winter chill, enjoying the spring blooms, or basking in the summer sun, Chicago offers a unique fashion experience. 

Check out the city’s diverse boutiques and support local businesses while staying comfortably chic throughout your journey. 

Happy shopping, and enjoy you stylish Chicago adventure!