Planning Your Outfit: What to Wear in Chicago in June

Chicago is known for its unpredictable weather, and June is no exception. As summer begins, the city’s fashion trends also start to shift, making it important to consider both the weather and fashion when planning your outfits.

While the weather can vary from warm and sunny to rainy and cool, the fashion scene in Chicago during June is anything but dull. From summer dresses to comfortable sneakers, there are plenty of stylish outfit options to choose from.

Key Takeaways:

  • It’s important to consider both the weather and fashion trends when planning your outfits in Chicago in June.
  • The city’s weather can range from warm and sunny to rainy and cool, so it’s important to dress in layers and choose cool, breathable fabrics.
  • Chicago’s fashion scene in June offers plenty of stylish options, including summer dresses and comfortable sneakers.

Embracing Summer Fashion in Chicago

Chicago’s fashion scene is always buzzing, and June is no exception. With warmer temperatures and longer days, it’s the perfect time to experiment with new styles and trends. Here are some summer fashion tips for Chicago to ensure you stay stylish and comfortable.

Check Out the Chicago Style Guide

If you’re unsure of what to wear in Chicago in June, check out the Chicago style guide. This guide will help you get a better understanding of the city’s fashion trends and provide inspiration for your wardrobe. You can also look up fashion blogs and Instagram pages for more ideas and tips on what to wear.

Lightweight Fabrics are Key

Chicago can get quite humid during the summer months, so it’s essential to choose lightweight and breathable fabrics. Cotton, linen, and silk are great options as they allow for ventilation and keep you cool. Avoid synthetic fabrics as they tend to trap heat and moisture, making you feel uncomfortable.

summer fashion in Chicago

Accessorize with Chic Sunglasses

Not only are sunglasses a practical accessory for protecting your eyes from the sun, but they can also add an instant chic factor to any outfit. Choose a classic and versatile style that complements your face shape.

Don’t Shy Away from Colors and Prints

Summer is the perfect time to experiment with colors and prints. Don’t be afraid to add some bold and bright pieces to your wardrobe. Floral prints, stripes, and polka dots are all popular choices in Chicago during June.

Stay Comfortable with Sandals

Walking around Chicago during the summer months can be tiring, so it’s vital to have comfortable footwear. Sandals are a great option as they allow your feet to breathe and prevent blisters. Choose a pair with good support and cushioning for added comfort.

By following these summer fashion tips for Chicago, you’ll be able to dress stylishly while keeping cool and comfortable during the warm June weather.

Understanding Chicago’s June Weather

When it comes to dressing appropriately in Chicago in June, it’s important to understand the city’s weather patterns. June is typically a warm month in Chicago, with temperatures ranging from the mid-60s to mid-80s Fahrenheit. However, it’s not uncommon for the temperatures to drop suddenly, or for unexpected rainfall to occur.

Average Temperature Average Rainfall
65-85 °F 3.5 inches

It’s important to pack clothing that can easily be layered, as the temperature can fluctuate greatly throughout the day. Dressing in layers allows you to add or remove clothing as needed, ensuring that you stay comfortable all day long. In addition to layering, it’s also important to bring lightweight, breathable clothing, such as cotton or linen, to stay cool in the warm temperatures.

It’s always a good idea to check the weather forecast before heading out for the day, as sudden changes in weather can occur. Bringing a light rain jacket or umbrella is always a smart choice, as rain showers are not uncommon in Chicago during the month of June.

By understanding the weather patterns in Chicago during the month of June, you can dress appropriately and ensure that you stay comfortable throughout your visit to the Windy City.

what to wear in chicago in june

Dressing for Comfort and Versatility

June in Chicago can be unpredictable when it comes to weather, so it’s important to have outfits that are both comfortable and versatile. Opt for lightweight and breathable fabrics to stay cool during warm days, and layer up with jackets or cardigans for cooler evenings. Here are some outfit ideas for the Chicago summer wardrobe:

Outfit Description
outfits for Chicago in June Pair a flowy sundress with sandals and a denim jacket for a chic and comfortable outfit. This look is perfect for exploring the city during the day and transitioning to dinner or drinks at night.
outfits for Chicago in June For a more casual look, opt for a graphic tee, high-waisted shorts, and sneakers. This outfit is perfect for a day spent walking around the city or visiting a local park.
Chicago summer wardrobe If you’re planning to attend a summer festival or concert, consider wearing a romper or jumpsuit with comfortable shoes. This outfit is both stylish and practical for standing and dancing for extended periods of time.

Remember to also consider the activities you have planned for the day and the locations you will be visiting. Choose outfits that allow for ease of movement and are appropriate for the setting.

Layering for Changing Temperatures

Chicago’s weather during June can be unpredictable, with temperatures fluctuating throughout the day. The key to staying comfortable is to layer your clothing.

Start with a lightweight and breathable base layer, such as a cotton t-shirt or tank top. This will help keep you cool during the warmer parts of the day.

Next, add a lightweight jacket or cardigan that you can easily remove if the temperature rises. A denim jacket or a lightweight sweater are great options.

Layering Tips:
Choose breathable fabrics: Opt for natural fabrics like cotton or linen that allow airflow and keep you cool.
Avoid bulky items: Instead of a thick sweater, opt for a lighter layer that you can easily take off if needed.
Don’t forget about scarves: If it gets chilly, a lightweight scarf can add warmth without adding bulk.

Remember, the key is to dress in layers that you can easily remove or add as needed throughout the day. This will ensure that you stay comfortable no matter what the temperature is outside.

dressing for June in Chicago

Don’t Forget About Footwear

Choosing the right footwear is crucial when planning your Chicago summer wardrobe. With temperatures averaging around 75°F and occasional rain showers, you want to make sure your shoes are both stylish and functional. Comfortable sneakers or sandals are great options for walking around the city, while closed-toe shoes or boots are suitable for chillier days or rainy weather.

It’s also important to keep in mind the activities and locations you’ll be visiting in Chicago. If you plan on spending time at the beach or near the lakefront, opt for water-resistant sandals or flip flops. For a night out, dress up your outfit with a pair of stylish heels or dressy boots.

what to wear in Chicago in June

When it comes to footwear, remember to prioritize comfort and practicality while still maintaining your personal style. By choosing the right shoes, you can enjoy all that Chicago has to offer without sacrificing your fashion sense.

Accessorizing for Style and Practicality

Accessories are an essential part of any outfit, and they can make or break a look. In Chicago, where fashion is a crucial aspect of daily life, accessorizing is a must for a stylish appearance. But, it’s not just about looking good; accessories should also be functional and practical. Fortunately, there are many accessories that can enhance both style and practicality when dressing for June in Chicago. Here are some suggestions to help you accessorize like a true Chicagoan.

1. Sunglasses

Chicago summers can get bright and sunny, which makes sunglasses a must-have accessory. Not only do they protect your eyes from harmful UV rays, but they also add an edge to your outfit. When choosing sunglasses, go for a pair that complements your face shape and personal style. Aviators and wayfarers are classic options that never go out of style, but you can also opt for trendy shapes like cat-eye or round sunglasses.

2. Scarves

Scarves are versatile accessories that can add a pop of color or pattern to any outfit. In June, when temperatures can fluctuate, a lightweight scarf can also provide an extra layer of warmth. There are endless styles and materials to choose from, including silk, cotton, or linen. Consider pairing a bold print scarf with a neutral outfit to add visual interest or complement a monochrome outfit with a contrasting colored scarf.

3. Hats

Hats are another practical accessory that can also elevate your outfit. A wide-brimmed hat can protect your face and neck from the sun, while a beanie can keep you warm on a windy day. Choose a hat that suits your personal style and the occasion. Fedora hats are a chic choice for a casual daytime look, while a beret can add sophistication to an evening outfit.

4. Bags

A good bag is essential for carrying your daily necessities, but it can also be a stylish accessory. In June, consider opting for a crossbody or backpack style that allows for hands-free movement. Look for bags made of durable materials that can withstand the elements, such as leather or nylon. Choose a classic style that can transition from day to night and from work to play.

Chicago fashion accessories

In conclusion, accessorizing is a crucial part of dressing in Chicago, especially in June when fashion and functionality are equally important. Sunglasses, scarves, hats, and bags are all accessories that can enhance both style and practicality. By incorporating these items into your wardrobe, you can create outfits that not only look great but also keep you comfortable and prepared for whatever the Chicago weather brings.

Cool and Breathable Fabrics

When it comes to dressing for June in Chicago, it’s important to choose fabrics that are both cool and breathable. The warm weather can make it uncomfortable to wear heavy and non-breathable clothing. Choosing the right fabric can make all the difference in staying comfortable and stylish in the Windy City.

One fabric that is perfect for Chicago’s June weather is cotton. It’s lightweight, breathable, and easy to care for. Cotton is versatile and can be worn in many styles, from dresses to shorts to t-shirts. Linen is another great option for staying cool during the warm weather. It’s breathable, lightweight, and has a natural texture that looks effortlessly chic.

Another fabric to consider is rayon. It’s a synthetic fabric that has a similar texture to cotton, but with a sleek and smooth finish. Rayon is lightweight, breathable, and perfect for a variety of clothing styles. Be careful with rayon, as it tends to wrinkle easily, so it’s important to hang or fold your garments after wearing them.

Lastly, silk is a luxurious fabric that is perfect for dressing up during Chicago’s June events. It’s lightweight, breathable, and has a natural sheen that adds elegance and sophistication to any outfit.

When selecting your Chicago summer wardrobe, be sure to consider these cool and breathable fabrics to ensure comfort and style all month long.

summer fashion in Chicago

Navigating Chicago’s Dress Codes

Chicago is a city with diverse social and cultural scenes, with varying dress codes for different occasions, making it crucial to consider and adhere to the appropriate dress codes when dressing up for events or places. The city prides itself on its stylish yet practical fashion sense, which translates to a balance of chic and comfort dressing, even in formal situations.

For outdoor events or casual hangouts, dress codes tend to be more relaxed, with common attires including shorts, jeans, t-shirts, sundresses, and sandals. However, the comfort level of the clothing should not compromise the overall look of the outfit. To ensure a fashionable yet relaxed look, consider choosing breathable and lightweight fabric to beat the heat, accessorizing, and adding appropriate footwear.

Dress Codes for Business

Business dress codes in Chicago, much like any other business district, tend to lean towards professional and conservative attire. It’s advisable to skip anything too flashy, too casual, or too revealing. Common business dress codes include suits, blouses, trousers, skirts or dresses, and closed-toe shoes. Men may choose to wear ties or jackets for more formal meetings, but it’s not mandatory. Additionally, it’s important to maintain the professional image with clean and polished shoes, hair, and nails.

When attending evening events like dinners, cocktail parties, or galas, it’s essential to keep in mind the level of formality of the gathering. Men may wear a suit or tuxedo, while women can wear evening gowns, cocktail dresses, or dressy separates. Accessories such as watches, jewelry, and clutch bags can also enhance the look of the outfit.

Lastly, it’s crucial to research and understand the specific dress code of an event or establishment before attending, as some venues may have strict policies that enforce dress codes. By considering the dress codes in Chicago, one can dress appropriately for the occasion, and at the same time, make a stylish statement.

dressing in Chicago in June

Whether you’re visiting or residing in Chicago, it’s important to always dress appropriately for the occasion while maintaining a sense of personal style. By following the Chicago style guide, one can ensure a stylish and comfortable experience in the city, no matter the event or location.

Staying Chic During Rainy Days

Chicago’s unpredictable weather can make dressing for June a challenge, especially on rainy days. But don’t let the rain dampen your style! There are plenty of fashion-forward ways to stay dry during your Chicago adventures.

First and foremost, invest in a quality raincoat or trench coat. Look for a style that is both functional and fashionable, with a waterproof material and a flattering silhouette. Pair it with a pair of rain boots or waterproof sneakers for added protection.

If you prefer to wear regular shoes, be sure to bring an umbrella or a stylish rain hat to keep your outfit from getting soaked. And don’t forget to accessorize with a fun, bright-colored scarf or hat to add a pop of color to your rainy day ensemble.

what to wear in Chicago in June

When it comes to clothing, opt for lightweight, quick-drying pieces that won’t leave you feeling weighed down. A simple cotton t-shirt or blouse paired with comfortable jeans or leggings can be dressed up or down, depending on your plans for the day.

And finally, consider adding a splash of color or pattern to your rainy day outfit with a fun printed umbrella or a statement piece of jewelry. Not only will it brighten your mood, but it will also make your outfit stand out in a sea of black umbrellas.


In summary, dressing for June in Chicago requires careful consideration of both the fashion trends and weather conditions. To stay stylish and comfortable, it is important to prioritize cool and breathable fabrics, and to layer clothing for changing temperatures.

For those looking to embrace summer fashion trends in Chicago, versatile outfits and appropriate footwear are key. Accessorizing can also enhance both style and practicality in the Windy City.

When navigating Chicago’s dress codes, it is important to dress appropriately for various occasions, while also staying true to personal style.

And for those rainy days, staying chic and dry is possible with the right clothing and accessories.

With these tips in mind, anyone can confidently plan their outfit for a stylish and comfortable experience in Chicago during the month of June.


Q: What should I wear in Chicago in June?

A: It’s important to consider both the fashion trends and weather conditions in Chicago during June. Opt for lightweight and breathable fabrics to stay cool, and layer your clothing to accommodate for the fluctuating temperatures. Don’t forget to pack comfortable footwear for walking around the city.

Q: How do I dress stylishly in Chicago during June?

A: Embrace summer fashion trends in Chicago by incorporating vibrant colors and lightweight fabrics into your outfits. Accessorize with stylish and practical accessories, and don’t be afraid to experiment with different styles and patterns. Remember to dress appropriately for various occasions and dress codes in the city.

Q: What should I do if it rains in June in Chicago?

A: Prepare for rainy days in Chicago by bringing along a lightweight and waterproof jacket or umbrella. Opt for shoes that are water-resistant or bring a spare pair of shoes to change into. Consider layering your clothing with a light rain jacket or a waterproof hat to protect yourself from the rain.

Q: How can I stay comfortable in Chicago’s changing temperatures during June?

A: Layering is key to staying comfortable in Chicago’s fluctuating temperatures. Start with a lightweight base layer, add a sweater or jacket for warmth, and top it off with a light scarf or shawl for versatility. This will allow you to adjust your clothing throughout the day as the temperatures change.

Q: What footwear is suitable for June in Chicago?

A: Choose footwear that is both stylish and comfortable for walking around the city. Opt for sneakers or sandals with good arch support for maximum comfort. Make sure your shoes are well-cushioned and breathable to keep your feet cool and comfortable throughout the day.

Q: What are some recommended fabrics for clothing in Chicago in June?

A: Choose cool and breathable fabrics such as cotton, linen, and lightweight blends. These fabrics allow air to flow freely, keeping you comfortable in Chicago’s warm weather. Avoid heavy fabrics that can trap heat and make you feel uncomfortable.

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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