Deciding What to Wear in Chicago in August: A Guide

If you’re planning a trip to Chicago in August, it’s important to consider the city’s summer fashion and weather. With temperatures ranging from the mid 60s to the high 80s, it’s crucial to have a versatile wardrobe that can adapt to the changing weather conditions. This guide will provide you with essential tips on what to wear in Chicago in August, so you can stay comfortable and fashionable throughout your stay.

Key Takeaways:

  • Chicago’s August weather can be unpredictable, with temperatures ranging from the mid 60s to the high 80s.
  • Embrace Chicago’s summer style by incorporating lightweight and breathable clothing into your wardrobe.
  • Layering is key for cooler evenings in Chicago, so make sure to bring a light jacket or cardigan.
  • Choose comfortable footwear that can withstand various terrains and weather conditions when exploring the city.
  • Accessorize with trendy sunglasses, hats, and scarves to add style to your outfits while serving a functional purpose.
  • Pack light and choose versatile clothing items to maximize your suitcase space, and don’t forget to dress for specific events or festivals.

Understanding Chicago August Weather

Chicago in August can get very hot and humid, with temperatures averaging around 79°F (26°C). This means it’s important to dress light and wear breathable clothes to avoid overheating.

In addition, occasional thunderstorms are common during this time of year, so it’s a good idea to bring a rain jacket or umbrella with you when you venture out in the city. Remember, it’s better to be prepared for any weather conditions that might come your way.

When it comes to clothing, opt for lightweight and loose-fitting clothes made of breathable fabrics like cotton or linen. Avoid synthetic materials, as they can trap heat and make you feel uncomfortable.

For men, avoid wearing dress shirts or suits unless necessary. Go for polo shirts or lightweight t-shirts paired with shorts or chino pants. Women can choose from sundresses, skirts, and shorts paired with a tank top or blouse.

It’s also important to wear comfortable shoes that allow for walking long distances as Chicago is a great city to explore on foot. Consider sneakers or sandals, but avoid flip-flops as they offer little support and can be uncomfortable for extended use.

Chicago August Weather Outfits

By dressing appropriately for the hot and occasionally rainy August weather in Chicago, you’ll be able to fully enjoy all that the city has to offer.

Embracing Chicago Summer Style

Chicago is known for its fashion-forward residents and their bold sense of style. In August, the city is buzzing with summer energy and fashion trends.

To embrace Chicago summer style, start by incorporating bright colors and bold prints into your wardrobe. Think floral dresses, graphic tees, and statement accessories. A popular trend right now is incorporating neon accents into outfits for a fun pop of color.

It’s important to dress for both day and night activities, so consider versatile pieces that can be dressed up or down. Chic jumpsuits, trendy rompers, and summer shorts paired with a blouse or tank top are all great options.

what to wear in chicago in august

When it comes to shoes, comfortable sandals or sneakers are essential for walking around the city. For a more dressed up look, try a pair of block heels or wedges.

Accessories are the perfect way to complete any outfit. Trendy sunglasses, statement earrings, and of course, a stylish face mask are all must-haves. Don’t be afraid to mix and match accessories to create a unique look that reflects your personal style.

Overall, embracing Chicago summer style is about being confident and having fun with your fashion choices. Incorporate the latest trends while still staying true to your personal style. With these tips, you’ll be ready to hit the streets of Chicago in style.

Essential Wardrobe Staples for August

August in Chicago can be hot and humid, so it’s important to choose clothing items that are lightweight and breathable. Here are some essential wardrobe staples to consider:

Item Description
Flowy Tops Avoid tight-fitting tops and opt for flowy blouses or tank tops made with light fabrics such as cotton or linen.
Shorts Shorts are a must-have for staying cool in Chicago’s hot weather. Choose denim shorts or other breathable materials that are comfortable for walking around in the city.
Maxi Dresses Maxi dresses are versatile and perfect for dressing up or down. Look for dresses made with light materials and breathable fabrics.
Sandals Sandals are essential for exploring the city in August. Opt for comfortable and supportive sandals that are suitable for walking long distances.
Hats A wide-brimmed hat is not only fashionable but also helps to protect against the sun’s harmful rays. Choose a lightweight hat that can be easily packed for convenience.
Sunglasses With the sun shining brightly during the day, protect your eyes from glare and harmful UV rays with a stylish pair of sunglasses.

These wardrobe staples can be mixed and matched to create various outfits suitable for Chicago’s August weather. Remember to choose breathable fabrics and clothing items that are comfortable for walking around the city.

chicago august wardrobe essentials

Dressing for Warm Days

Chicago in August can be scorching hot, so it’s important to dress appropriately for warm weather. This section will provide you with some outfit ideas to keep you cool and stylish. Whether you’re exploring the city or attending an outdoor event, these outfits will keep you comfortable.


Sundresses are a perfect choice for hot days in Chicago. They’re lightweight, breezy, and come in a variety of styles. From flowy maxi dresses to fitted midi dresses, there’s a sundress for every occasion. Pair with sandals or sneakers for a casual look, or dress it up with heels for a night out.

dresses for august in chicago

Shorts and Tank Tops

If you prefer a more casual look, shorts and tank tops are a great option. Opt for cotton or linen materials to keep you cool in the heat. Pair with sneakers or sandals and a crossbody bag for a practical and effortless look. Don’t forget to wear sunscreen and bring a hat to protect yourself from the sun.

Skirts and Crop Tops

For a trendy summer look, try pairing a flowy skirt with a crop top. This outfit is both comfortable and stylish, perfect for exploring the city or attending a summer festival. Choose a skirt with a bold pattern or color to make a statement, and pair with comfortable sandals or sneakers.

Layering for Breezy Nights

Chicago weather in August can be unpredictable, with warm days and cooler nights. It’s important to be prepared for any temperature changes, especially if your plans include outdoor activities in the evening. Layering is the key to staying comfortable while still looking stylish.

One outfit idea is to pair a sundress with a denim jacket or a light cardigan. This gives you the option to remove the jacket if it gets too warm, or add it back on if the breeze picks up. Another option is to wear a lightweight blouse and high waisted shorts, topped with a flowy shawl. This adds an extra layer of warmth while still maintaining a summery look.

For men, a classic combination is a t-shirt and jeans, topped with a button-down shirt or a sweater. This provides flexibility to adjust to the changing temperatures. A light jacket or a blazer can also be added for a dressier look.

outfit ideas for august in chicago

When it comes to footwear, closed-toe shoes are a good choice for the cooler evenings. A pair of ankle boots or sneakers can easily be paired with any outfit. It’s also a good idea to bring a pair of socks in case it gets chilly.

Remember to bring a bag or a backpack to store your layers in case you need to remove them. This will also come in handy if it starts to rain. Overall, layering allows you to adapt to the changing Chicago weather while still looking fashionable.

Footwear for Exploring the City

When it comes to exploring the city of Chicago in August, it’s essential to have comfortable and sturdy footwear that can withstand the various terrains and weather conditions. The city is known for its beautiful parks, beaches, and iconic skyscrapers, so it’s important to have the right shoes to take in all the sights.

For those planning to do a lot of walking, athletic shoes or sneakers with good support are a wise choice. Look for materials that are breathable, such as mesh or canvas, to help keep your feet cool during the hot summer days. Sandals are also a popular choice, but make sure to opt for ones with straps that securely fasten to your feet to avoid any mishaps while exploring the city.

If you plan on visiting the beach, water shoes or sandals with a durable sole are a must. They will protect your feet from rocks or sharp objects while still allowing you to enjoy the water.

For a night out, dressy flats or low heels can be a comfortable option for walking around the city while still looking stylish. Avoid wearing high heels, as they can be challenging to navigate the city’s many cobblestone streets and uneven sidewalks.

Whatever footwear you choose, make sure to break them in before your trip to avoid any discomfort or blisters. Your feet will thank you for it as you explore all the wonders of Chicago in August.

what to wear in chicago in august

Accessorizing for Style and Function

When it comes to dressing for August in Chicago, accessorizing is key. Accessories can add a pop of color, texture, and personality to any outfit. They can also serve a functional purpose, such as protecting from the sun or adding warmth during cooler evenings.

One essential accessory for Chicago in August is sunglasses. These not only protect your eyes from the sun but also can add a stylish element to any outfit. Consider choosing a classic pair of aviators or experimenting with bold colors or unique shapes.

Hats are also a versatile accessory for August in Chicago. A wide-brimmed hat can provide shade and protection from the sun, while a beanie or fedora can add warmth during cooler nights. Scarves are another great accessory to consider. Not only do they add a touch of sophistication, but they can also be wrapped around the neck or shoulders for added warmth if needed.

chicago august fashion trends

Fashion is not necessarily about labels. It’s not about brands. It’s about something else that comes from within you. – Ralph Lauren

When it comes to other accessories, consider adding a statement piece such as a bold necklace or earrings that can add a touch of glamour to any outfit. For those looking to incorporate the latest fashion trends in Chicago during August, consider adding a colorful crossbody bag or oversized sunglasses.

Remember to have fun when accessorizing for August in Chicago. With so many options to choose from, you can mix and match accessories to create unique and stylish outfits no matter where your day takes you.

Packing Tips for Travelers

Visiting Chicago in August can be an enjoyable experience, but it is essential to pack the appropriate clothing and accessories. Here are some tips for packing wisely and maximizing suitcase space:

  1. Keep it lightweight: Choose lightweight clothing items that are easy to pack and won’t weigh down your luggage. Fabrics like cotton, linen, and rayon are great options as they are breathable and comfortable to wear in warm weather.
  2. Layer up: While Chicago is known for its hot summers, the temperature can drop at night, so it’s important to bring layers. A light sweater or jacket can help keep you warm and stylish when the sun goes down.
  3. Choose versatile pieces: Pack items that can be mixed and matched to create different outfits. A pair of jeans or shorts paired with different tops can make multiple ensembles, maximizing your wardrobe.
  4. Consider your activities: If you plan on attending specific events or activities like outdoor concerts or boat tours, be sure to pack appropriate clothing and shoes. A dressier outfit may be necessary for a night on the town, while comfortable shoes are a must-have for walking and exploring the city.
  5. Don’t forget your rain gear: August in Chicago means occasional rain showers, so make sure to bring a waterproof jacket or umbrella to stay dry.
  6. Accessorize: Accessorizing can be a great way to add a touch of flair to any outfit. Sunglasses, hats, and scarves are both fashionable and functional, protecting you from the sun and adding a pop of color to your outfit.

By following these packing tips, you can ensure that you are ready for any adventure in Chicago during August.

what to wear in chicago in august

Dressing for Special Events

August in Chicago is a busy month for events and special occasions. From weddings to outdoor concerts and rooftop parties, there are plenty of opportunities to dress up and show off your summer style. To help you look your best, here are some outfit ideas to consider:

  • For an outdoor wedding, opt for a flowy maxi dress in a bright or pastel color. Pair it with wedges or block heels for comfort on the grass and add a statement necklace to elevate the outfit.
  • For a rooftop party, embrace the Chicago summer style with a crop top and high-waisted shorts combination. Accessorize with hoop earrings, a crossbody bag, and strappy sandals.
  • For an outdoor concert or festival, choose a breezy sundress in a floral print and pair it with comfortable sandals or sneakers. Add a denim jacket or kimono for when the temperature drops in the evening.

When it comes to the latest fashion trends in August, bright colors, bold prints, and statement jewelry are all the rage. Don’t be afraid to experiment with different styles and patterns to find what suits you best.

outfit ideas for august in chicago
Outfit ideas for August in Chicago

Staying Fashionable in Chicago Rain

August in Chicago may bring some rainy days, but that doesn’t mean you have to sacrifice style for function. With the right clothing items, you can stay dry and fashionable at the same time.

First and foremost, invest in a good-quality rain jacket. Look for one that is both waterproof and breathable. A hooded option will also come in handy during those unexpected downpours.

Chicago August Weather Outfits

When it comes to footwear, select shoes or boots that are also waterproof. Avoid materials like suede or leather that may be damaged by water. Rubber or waterproof boots are a great option for staying dry and stylish.

Accessorize with a colorful umbrella to add a pop of color to your outfit. Look for one that is compact and easy to carry with you throughout the day.

Don’t forget to layer underneath your rain jacket in case the temperature drops. Opt for lightweight fabrics that won’t weigh you down but still provide warmth. A scarf or hat can also protect your hair and add an extra touch of style to your outfit.

With these tips, you can navigate the rain in Chicago during August without sacrificing your fashion sense.

Dressing with Style and Comfort in Chicago’s August

When it comes to fashion, Chicagoans know how to embrace the summer season. August in the city is no exception, with residents and visitors alike donning their best outfits for outdoor events, festivals, and more. However, with hot and humid weather to contend with, it’s important to find a balance between style and comfort.

One way to stay fashionable and comfortable in Chicago’s August weather is to embrace the summer fashion trends. From breezy dresses to flowy tops and shorts, there are plenty of options to choose from that are both stylish and lightweight. It’s also important to consider the specific weather conditions during this time of year. With average temperatures ranging from the mid-60s°F to the mid-80s°F, it’s crucial to choose clothing items that are breathable and comfortable.

Choosing Essential Wardrobe Staples

To create a versatile wardrobe for August in Chicago, it’s important to invest in essential pieces that can be mixed and matched to create a variety of outfits. Some key items to consider include lightweight dresses, denim shorts, flowy pants, and comfortable sandals. Accessorizing with sunglasses, hats, and scarves can also add a stylish touch to any outfit while serving a functional purpose.

Dressing for Warm Days and Breezy Nights

When dressing for warm days in Chicago during August, it’s important to choose clothing items that are lightweight and breathable. This can include cotton dresses, flowy skirts, and shorts paired with lightweight tops. For breezy nights, layering is key. Opt for a light jacket or cardigan that can be easily removed if the temperature rises. And don’t forget to bring along a scarf or shawl to stay warm when the evening breeze picks up!

Choosing the Right Footwear

Exploring Chicago’s many attractions during August requires comfortable footwear that can withstand various terrains and weather conditions. Sneakers, sandals, and flats are all great options for walking around the city. And if rain is in the forecast, waterproof boots or sneakers are a must-have to stay dry and comfortable.

Dressing for Special Events

Chicago’s August calendar is packed with special events and occasions, such as weddings, outdoor concerts, and rooftop parties. When dressing for these events, it’s important to take into account the specific dress code and location. Chic dresses, dressy shorts, and lightweight suits are all appropriate options depending on the event. And don’t be afraid to add some flair with bold accessories!

Dressing for Rainy Days

August in Chicago can also bring rainy days, but that doesn’t mean you have to sacrifice style for practicality. Investing in a stylish rain jacket and waterproof shoes can keep you dry while still looking fashionable. And be sure to opt for clothing items made of quick-drying materials to avoid feeling damp all day.

With these tips in mind, navigating Chicago’s August weather and fashion scene should be a breeze. Remember to find a balance between style and comfort, and embrace the summer fashion trends while keeping practicality in mind!


Q: What should I wear in Chicago in August?

A: In August, it is best to wear lightweight and breathable clothing to stay cool in the summer heat. Opt for dresses, skirts, shorts, and tops made from light fabrics. Don’t forget to bring a light jacket or cardigan for the cooler evenings.

Q: What kind of shoes should I wear in Chicago in August?

A: Comfortable shoes are essential for exploring the city in August. Choose footwear that can withstand long distances and various terrains. Sneakers, sandals, or flats are all good options.

Q: How can I stay fashionable in Chicago during August?

A: You can stay fashionable in Chicago during August by keeping up with the latest fashion trends and incorporating them into your outfits. Accessorize with sunglasses, hats, and scarves to add style to your look.

Q: What should I pack for my trip to Chicago in August?

A: When packing for Chicago in August, it is advisable to pack light and choose versatile clothing items. Pack a mix of summer clothes such as dresses, shorts, and tops, as well as a light jacket or cardigan for the cooler evenings.

Q: How should I dress for special events in Chicago in August?

A: For special events in Chicago in August, consider the dress code and the nature of the event. If it is an outdoor occasion, opt for a stylish dress or a nice pair of pants with a dressy top. Don’t forget to accessorize and add your personal touch to the outfit.

Q: What should I wear on rainy days in Chicago in August?

A: On rainy days in Chicago in August, it is important to dress appropriately and stay dry. Pack a waterproof jacket or raincoat, as well as waterproof footwear. Consider bringing an umbrella and wearing layers to stay comfortable.

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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