Decoding What to Wear in Chicago in the Fall – Guide 2021

As the leaves change colors and the temperature begins to drop, it’s important to dress appropriately for the fall weather in Chicago. From chilly mornings to sunny afternoons and cool evenings, Chicago’s autumn weather can be unpredictable. But don’t worry, we’ve got you covered with our ultimate fall fashion guide.

In this guide, we’ll explore the latest fall fashion trends in Chicago, provide tips on how to dress for the changing weather, suggest wardrobe essentials, and share ideas for layering and accessorizing. Whether you’re dressing for a casual day out or a formal event, we’ve got everything you need to look stylish and comfortable during the fall season in Chicago.

Table of Contents

Key Takeaways:

  • Chicago fall weather can be unpredictable, so dressing in layers is essential.
  • Wardrobe essentials for fall in Chicago include coats, sweaters, and boots.
  • Transitioning summer pieces and incorporating fall colors are great ways to update your wardrobe without breaking the bank.

Chicago Fall Fashion Trends

Chicago is a city that embraces fashion trends, and fall is no exception. As the weather cools down, the fashion scene heats up with new styles and trends. This season, fashion lovers in Chicago are turning to warm colors, comfortable fabrics, and vintage-inspired pieces.

Warm Colors

One trend that is gaining popularity is warm colors. This season, shades of orange, red, and brown are dominating the scene. Fashionistas in Chicago are incorporating these colors into their wardrobes through coats, sweaters, and accessories.

Chicago fall fashion trends

Comfortable Fabrics

Another trend that is popular in Chicago this fall is comfortable fabrics. Soft, cozy materials such as wool, cashmere, and flannel are being seen in everything from coats to pants to scarves. These comfortable yet fashionable fabrics are perfect for the notoriously chilly Chicago weather.

Vintage-Inspired Pieces

Vintage-inspired pieces are also making a comeback this season. From plaid skirts to retro jackets to chunky sweaters, Chicagoans are embracing these nostalgic pieces and putting their own modern twists on them. These vintage-inspired items add character and depth to any fall outfit.

If you want to stay up-to-date on the latest fall fashion trends in Chicago, be sure to incorporate these warm colors, comfortable fabrics, and vintage-inspired pieces into your wardrobe.

Dressing for Changing Weather in Chicago

Chicago’s fall weather can be unpredictable, with temperatures fluctuating throughout the day. The key to staying comfortable is to dress in layers. This way, you can adjust your clothing as needed as the weather changes.

Start with a base layer that is comfortable and breathable, such as a long-sleeved shirt or lightweight sweater. From there, add a mid-layer such as a cardigan or fleece jacket. Finally, top it off with a coat that is warm and waterproof to protect you from the wind and rain.

It’s also a good idea to wear versatile clothing items that can easily be adjusted throughout the day. For example, a scarf can be worn as a fashion accessory in the morning, but can also be wrapped around your neck for added warmth later in the day.

Don’t forget about your footwear as well. Closed-toe shoes or boots are a must to keep your feet dry and warm. And if the weather is particularly chilly, consider wearing wool or fleece-lined socks for added insulation.

Overall, the key to dressing for changing weather in Chicago is to be prepared for anything. By layering your clothing, wearing versatile items, and choosing appropriate footwear, you can stay comfortable and stylish as you navigate the windy city’s fall weather.

fall weather in Chicago

Wardrobe Essentials for Fall in Chicago

As the temperature begins to drop and the leaves turn shades of red and gold, it’s time to start thinking about your fall wardrobe essentials. In Chicago, where the weather can be unpredictable, it’s important to have versatile clothing items for mixing and matching.

Coats: A warm and stylish coat is a must-have for fall in Chicago. Consider a wool or down coat that can withstand the wind and chilly temperatures. Black, navy, and camel colors are timeless and versatile options.

wardrobe essentials for fall in Chicago

Sweaters: Sweaters are perfect for layering and adding texture to your outfit. Opt for chunky knits, turtlenecks, and cardigans in neutral colors like beige, gray, and cream.

Boots: Chic and comfortable boots are a staple for fall in Chicago. Ankle boots, knee-high boots, and combat boots can be worn with dresses, skirts, and pants. Black, brown, and burgundy are classic colors to choose from.

Jeans: Denim is a year-round favorite, but in fall, it can be paired with cozy sweaters and jackets. High-waisted, straight-leg, and skinny jeans are all popular styles. Dark washes and black denim are sophisticated and slimming options.

Accessories: Scarves, hats, and gloves are essential for staying warm and adding personal style to your outfit. Look for wool, cashmere, or knit fabrics in neutral colors or statement patterns.

These wardrobe essentials can be mixed and matched to create endless outfit options for fall in Chicago. Aim for a cohesive and versatile wardrobe that can be easily adjusted to accommodate the changing weather conditions.

Layering Tips for Fall in Chicago

When it comes to dressing for the fall weather in Chicago, layering is key. The temperature can fluctuate throughout the day, making it essential to be able to add or remove layers as needed. Here are some layering tips to help you stay comfortable and stylish:

Start with a base layer

The first layer of your outfit should be a lightweight, breathable fabric that will help regulate your body temperature. Consider wearing a long-sleeved shirt or a thin sweater.

Add a mid-layer for warmth

For the second layer, choose a thicker, warmer piece such as a sweater, cardigan, or fleece jacket. This layer will add warmth to your outfit and can be easily removed if you get too hot.

Finish with an outer layer

Finally, add an outer layer to protect yourself from the wind and rain. A classic trench coat or a stylish leather jacket are great options for fall in Chicago. Make sure to choose a coat that is versatile and can be dressed up or down to complement different outfits.

Layering tips for fall in Chicago

Accessorize with scarves and hats

Scarves and hats are not only stylish but also practical accessories for fall in Chicago. They can add warmth and texture to your outfit while also protecting your head and neck from the chilly wind. Choose scarves and hats in neutral colors that can easily complement different outfits.

Experiment with different textures

Layering is also a great opportunity to experiment with different textures and fabrics. Consider mixing and matching materials such as denim, wool, suede, and leather for a more interesting and dynamic look.

Don’t forget about footwear

To complete your fall outfit, make sure to choose footwear that is both comfortable and appropriate for the weather. Ankle boots are a great option as they can be dressed up or down and provide protection from the rain and cold.

By following these layering tips, you’ll be able to stay comfortable and stylish while navigating the unpredictable weather of fall in Chicago.

Dressing Stylishly in Chicago During Fall

Chicago’s fall season offers the perfect opportunity to dress up in stylish, cozy outfits that embrace the changing season. From layered clothing to autumnal hues, here are some tips for dressing fashionably during fall in Chicago.

Warm and Cozy Layers

Dressing in layers is key during fall in Chicago due to the fluctuating temperatures. Opt for cozy knit sweaters, cardigans, and vests that can easily be removed as the day warms up. Scarves, hats, and gloves are also essential accessories that keep you warm and add a stylish touch to your outfit.

For a chic look, try layering a sweater over a collared shirt or wearing a turtleneck under a blazer. These versatile combinations can easily transition from casual to more formal events.

Boots for All Occasions

A good pair of boots is a fall wardrobe essential in Chicago. From ankle boots to knee-high boots, there are endless options to choose from. Ankle boots are perfect for everyday wear, while knee-high boots add a touch of sophistication to any outfit. Chelsea boots are also a popular choice, versatile for both casual and formal occasions.

For a trendy look, try pairing knee-high boots with a sweater dress or midi skirt. Ankle boots look great with jeans or leggings, layered with a long cardigan or oversized sweater.

Autumn Outfits for Chicago

Autumnal Hues

Chicago’s fall fashion scene often features warm, earthy hues like burnt orange, deep red, and mustard yellow. These colors perfectly reflect the changing leaves and add a touch of seasonal flair to any outfit.

For a timeless look, pair a white collared shirt with dark skinny jeans and a rust-colored trench coat. A deep red sweater paired with a plaid skirt and knee-high boots is perfect for a cozy, yet stylish ensemble.

Accessorize with Scarves and Hats

Scarves and hats are not only functional for staying warm during fall in Chicago, but also add a stylish finishing touch to any outfit. Infinity scarves, blanket scarves, and knit beanies are stylish options that keep you warm while complementing a variety of outfits.

Hats such as fedoras and berets are perfect for adding a chic touch to your fall ensemble. Whether paired with a sweater and jeans or a midi dress and boots, these accessories will elevate your look.

By incorporating these fall fashion tips into your wardrobe, you’ll be stylishly prepared for the changing weather in Chicago. From cozy layers to trendy boots, embrace the season’s fashion trends for a chic and comfortable look.

Incorporating Chicago’s Fall Colors

Chicago’s fall color palette is dominated by warm, earthy hues that reflect the changing foliage. Think rich browns, deep greens, vibrant oranges, and bold yellows. Incorporating these colors into your fall outfits can help you embrace the season and stand out in the city’s fashion scene.

One way to incorporate fall colors into your outfit is by wearing a statement piece in a bold hue. This could be a bright orange sweater, a deep green coat, or a mustard yellow scarf. Pairing this with neutral-colored complementary items, such as black jeans or brown boots, can create a balanced and stylish look.

Another way to add fall colors to your wardrobe is through accessories. A plaid scarf with warm tones can instantly elevate a look and add a touch of autumnal flair. Additionally, a patterned bag or hat with fall tones can be a subtle yet effective way to incorporate the seasonal colors into your outfit.

When choosing fall colors to incorporate into your outfit, it’s important to consider your skin tone and personal style. Not everyone may feel comfortable wearing head-to-toe orange or yellow, and that’s okay. Experimenting with different hues and finding what works for you is key to feeling confident and comfortable in your outfit.

Fall Leaves

Stylish Outerwear for Chicago’s Fall

As temperatures drop in Chicago during the fall season, a stylish and practical outerwear piece is essential to complete any autumn outfit. From cozy coats to sleek jackets, there are plenty of outerwear options that are perfect for the Windy City.

One popular choice for fall in Chicago is a classic wool coat. This timeless piece can easily be dressed up or down and is a staple in many wardrobes. A trench coat is also a great option for its versatility and ability to keep you dry during rainy fall days.

For a more casual look, try a denim or leather jacket. These styles can add a touch of edge to any outfit and are perfect for layering. A bomber jacket or puffer vest are also practical options for cooler days.

When it comes to color, neutral tones such as black, gray, and camel are popular choices. They pair well with any outfit and are timeless. However, don’t be afraid to add a pop of color or pattern to your outerwear for a statement piece.

Stylish Outerwear for Chicago's Fall

No matter what style or color you choose, ensure your outerwear piece is both functional and fashionable. With Chicago’s unpredictable weather, a good coat or jacket will become a fall wardrobe staple.

Dressing Stylishly in Chicago During Fall

Dressing for the fall season in Chicago can be tricky as the weather changes frequently. However, you can still look fashionable while staying warm and comfortable. Here are some tips and outfit ideas to help you dress stylishly in Chicago during fall:

1. Layering is Key

Layering is an essential technique to keep you warm during Chicago’s fall season. Start with a lightweight base layer such as a long-sleeved shirt or a turtleneck. Add a sweater or a light jacket on top and finish with a coat or a heavier jacket. Remember to choose fabrics that allow you to move comfortably, like wool, cashmere, or fleece.

For a chic layered outfit, try pairing a plaid shirt with a sweater vest, skinny jeans, and ankle boots. You can also try layering with a denim jacket, a hoodie, and a puffer vest for a more casual look.

2. Mix and Match Colors and Textures

Don’t be afraid to mix and match different colors and textures to create a stylish outfit. Try pairing neutral colors like beige, black, and gray with bold colors like red, wine, and navy blue. You can also experiment with textures like corduroy, leather, and suede to add depth and interest to your outfit.

For example, you can pair a plaid shirt dress with a leather jacket and over-the-knee boots for a chic and edgy look. Or, try wearing a chunky knit sweater with a tweed skirt and knee-high boots for a more sophisticated outfit.

3. Accessorize with Scarves, Hats, and Gloves

Accessorizing with scarves, hats, and gloves is a fun and practical way to add warmth and style to your fall outfits. Choose accessories that complement your outfit and reflect your personal style.

For instance, try wearing a colorful scarf with a classic trench coat and ankle boots. Or, top off your outfit with a statement hat like a fedora or a wide-brimmed hat. Leather gloves are also a great addition to any fall outfit, especially when paired with a wool coat.

dressing for changing weather in Chicago

4. Dress Up Your Denim

Denim is a staple in any wardrobe, and it can be dressed up or down depending on the occasion. Pair your favorite pair of jeans with a blouse and heels for a sophisticated look, or dress them down with a cozy sweater and sneakers for a more casual outfit.

You can also try layering denim with denim for a trendy look. Try pairing a chambray shirt with distressed jeans and ankle boots, or a denim jacket with a denim skirt and knee-high boots.

By following these tips and outfit ideas, you can dress stylishly while staying comfortable and warm during the fall season in Chicago.

Accessorizing for Fall in Chicago

When it comes to fall fashion in Chicago, accessories can make a big difference in elevating your outfit. Not only do they add visual interest to your look, but they can also provide essential warmth and comfort during the colder months. Here are some tips for accessorizing your autumn outfits for Chicago.

1. Hats

A stylish hat can not only keep you warm, but it can also serve as a statement piece for your outfit. Opt for a classic beanie or a trendy beret in a neutral color for a versatile option that can be worn with multiple outfits. For a more elevated look, try a fedora or a wide-brimmed hat in a rich fall hue.

2. Scarves

Scarves are a must-have accessory for fall in Chicago. A chunky knit scarf can provide warmth and texture to a simple outfit, while a silk scarf can add a pop of color and sophistication to an ensemble. For a chic layered look, try styling a long scarf wrapped around your neck or draped over your shoulders.

3. Gloves

Keeping your hands warm is essential during the cooler months in Chicago. Opt for a pair of leather gloves for a classic and stylish look, or try a pair of cozy knit gloves for a more casual vibe. For a fashionable twist, experiment with gloves in different colors or prints.

4. Jewelry

Jewelry can add a touch of personality to any outfit. Try layering delicate necklaces or stacking bracelets for a trendy look that can be dressed up or down. For a bolder statement, try a pair of statement earrings or a chunky necklace in a fall-inspired color.

5. Bags

A stylish bag can be both functional and fashionable. A crossbody bag is a great option for hands-free convenience, while a structured tote can add polish to a work outfit. For a trendy option, try a bucket bag or a mini backpack in a neutral color.

fall fashion in Chicago

Accessorizing your fall outfits in Chicago is all about layering and adding visual interest to your look. By incorporating hats, scarves, gloves, jewelry, and bags, you can stay warm and stylish throughout the season.

Dressing Stylishly in Chicago during Fall

Chicago is a city that loves fashion, regardless of the season. Dressing for fall in Chicago does not mean sacrificing style for warmth. In fact, there are plenty of stylish ways to embrace the season’s trends while staying cozy.

For a chic and effortless look, start with a comfortable pair of jeans or pants and a cozy sweater. Sweaters are a fall staple, and for good reason. They are versatile, stylish, and keep you warm. For a more polished look, swap out the sweater for a blouse or button-up shirt.

Accessories are key to completing any outfit. In Chicago, fall is the perfect time to experiment with hats, scarves, and gloves. A stylish fedora or a cute beanie can add a touch of personality to any outfit, while a cozy scarf and gloves keep you warm from head to toe.

Footwear is also essential in any fall wardrobe. In Chicago, ankle boots are the perfect choice. They are comfortable, stylish, and versatile. For a dressier occasion, a knee-high boot paired with a skirt or dress is a great option.

Don’t be afraid to mix and match fall trends and colors to create a unique and stylish look. Chicago is a city that loves to express itself through fashion, and fall is no exception.

Chicago Fall Fashion Tips

If you’re looking for more specific fashion tips for fall in Chicago, here are a few to consider:

  • Layer, layer, layer! The weather in Chicago is unpredictable, so it’s important to be prepared for both warm and cool temperatures.
  • Incorporate fall colors like burgundy, olive, and navy into your wardrobe.
  • Invest in a warm coat that is both stylish and practical.
  • Don’t be afraid to mix and match patterns, such as plaid and stripes.
  • Add a pop of color to your outfit with a bold accessory, like a statement necklace or brightly colored bag.

By following these tips, you’ll be sure to stay stylish and comfortable throughout the fall season in Chicago.


Q: What should I wear in Chicago in the fall?

A: It is best to dress in layers to accommodate the changing weather. Start with a lightweight sweater or long-sleeve shirt, and top it off with a jacket or coat. Don’t forget to bring an umbrella as well, as Chicago’s fall weather can be unpredictable.

Q: What are the current fashion trends for fall in Chicago?

A: Popular trends for fall in Chicago include earthy tones, plaid patterns, and oversized sweaters. Incorporate these trends into your wardrobe by choosing clothing items in these styles and colors.

Q: How can I dress stylishly in Chicago during the fall?

A: To dress stylishly in Chicago during the fall, focus on layering and accessorizing. Add scarves, hats, and statement jewelry to elevate your look. Don’t be afraid to mix and match different textures and patterns for a fashionable ensemble.

Q: What are the must-have wardrobe essentials for fall in Chicago?

A: Essential clothing pieces for fall in Chicago include a warm coat, comfortable boots, a cozy sweater, and versatile bottoms such as jeans or leggings. These items will keep you prepared for the fluctuating temperatures and changing weather.

Q: How do I transition my summer pieces into my fall wardrobe in Chicago?

A: To transition summer pieces, add layers and pair them with fall-appropriate items. For example, wear a sundress with a denim jacket or a maxi skirt with a chunky sweater. This way, you can continue to wear your favorite summer pieces while staying warm in Chicago’s fall weather.

Q: What colors are popular for fall fashion in Chicago?

A: Colors that dominate Chicago’s fall fashion scene include warm hues like burgundy, mustard yellow, and olive green. Incorporate these colors into your outfits through clothing choices or accessories to embrace the autumnal atmosphere.

Q: What outerwear options are suitable for fall in Chicago?

A: Suitable outerwear options for fall in Chicago include trench coats, leather jackets, and wool coats. These pieces will keep you warm and stylish during the cooler months. Consider investing in a versatile coat that can be dressed up or down for different occasions.

Q: How can I accessorize for fall in Chicago?

A: Accessorize for fall in Chicago by adding hats, scarves, gloves, and statement jewelry to your outfits. These accessories not only add style but also provide extra warmth and protection against the chilly winds.

Q: How should I dress for changing weather in Chicago during the fall?

A: Dress in layers to accommodate the changing weather. Start with a lightweight base layer, add a sweater or cardigan for warmth, and top it off with a jacket or coat that you can easily remove if the temperature rises. This way, you’ll be prepared for whatever weather comes your way.

Q: What is the importance of dressing appropriately for the fall weather in Chicago?

A: Dressing appropriately for the fall weather in Chicago is important to stay comfortable and avoid discomfort. The temperature can vary greatly during the day, so dressing in layers allows you to adjust your clothing to the changing conditions. It also ensures that you’re prepared for any unexpected weather changes.

Katie Sophia

Hey there! I'm Katie Sophia - your go-to gal for all things style at With a love for fashion and a knack for picking the perfect outfit, I'm here to make dressing for any event a breeze. I believe in looking fabulous without the fuss. Join me as we conquer the fashion world one outfit at a time!

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