Classic American Style: Summer Outfit Ideas for Men in Chicago

Classic American Style: Summer Outfit Ideas for Men in Chicago

Whether you are a Chicago native or simply visiting the windy city for the first time, it doesn’t take long to discover that windy isn’t Chicago’s only weather condition. If you are spending any length of time in the city throughout the summer season, you can stay cool and comfortable by preparing your wardrobe for hot, humid weather. In this post, we will take a look at classically American summer styles for men in Chicago---all of which are designed with both fashion and comfort in mind.

Style Ideas

When putting together outfits for the summer season in Chicago, reflect on your personal style. Maybe you have one style or a combination of several styles. Below we have highlighted a few style ideas for inspiration:

Preppy Style: You can achieve the timeless preppy style with a sleek polo shirt in a bright color (such as light blue or pink) paired with khaki shorts and boat shoes. To add some texture to the look, incorporate accessories like a woven belt or aviator sunglasses.

Casual Beachy: For a more laid-back beach look, try a graphic t-shirt with colorful board shorts and flip-flops. Don’t forget to protect your face from the sun with a sporty baseball cap and a pair of shades.

Sporty Chic: If you’re into sports or simply appreciate the athleisure style, try a jersey or a tank top with athletic shorts and running sneakers. This look is perfect for casual hangouts, gym sessions, long jogs in the city, or lake days around the area.

Business Casual: If you need to dress up for work but still want to stay cool in the heat, try a lightweight blazer over a collared shirt with dress shorts and loafers. You can also add a colorful print pocket square to add dimension and contrast to your look.

Outfit Ideas

Once you determine what styles you enjoy wearing the most, you can get more specific with outfit ideas. We’ve come up with a few men’s outfits that are perfect for transitioning from day to night during the summer:

Linen suit: A lightweight and breathable linen suit in a light color such as beige or light gray pairs well with a collared shirt and dress shoes. To transition this outfit into nighttime, you could swap out the dress shoes for a pair of leather loafers or white sneakers (depending on the formality of the event).

Short-sleeved button-up: Switch out your usual long-sleeved button-up for a short-sleeved one in a light and airy fabric such as cotton or linen. Experiment with bright colors or bold, summery prints for a playful, trendy look. For a look that can be worn both in the office and on a night out, tuck the shirt in and add a sleek leather belt. Swap out the dress shoes for Chelsea boots and add a lightweight blazer for a more sophisticated feel.

Cardigan and dress pants: For a more casual yet still professional look, try pairing a lightweight men’s cardigan sweater with dress pants and dress shoes and complete the ensemble with a belt and a watch. If you are going from daytime to nighttime, incorporate additional accessories, such as a patterned scarf or tie that will add texture to the outfit.

Casual, Athletic Outfits

If you are looking for timelessly trendy off-duty outfits, consider these athletic styles, perfect for casual social events, relaxing days at home, or outdoor adventures in the city:

Joggers and a hoodie: This classic sporty look can be elevated by choosing a well-fitted hoodie and joggers with a tapered leg. Don’t forget to complete your outfit with statement high-top sneakers!

Athletic shorts and a sweatshirt: Opt for men’s athletic shorts with a fun pattern and pair them with a crewneck sweatshirt for a casual, sporty look. Add sandals or slip-on sneakers for a laid-back vibe ideal for daytime and evening activities.

Windbreaker and joggers: If you have a rainy day ahead of you, choose a lightweight windbreaker and pair it with joggers. Add a simple baseball cap to complete the outfit (and shield your face from the rain).

The Most Comfortable Pieces

The summer months in Chicago can be quite warm and humid, so always strive to choose clothing that is lightweight and breathable. Some popular trends in the city include:

Printed button-down shirts: Short-sleeve or long-sleeve button-down shirts in a cotton material are a great way to add personality to your summer wardrobe, especially if you opt for tops with bold prints like florals, tropical patterns, or geometric shapes.

Linen and cotton fabrics: Both of these materials are perfect for staying cool in the heat, and you can find everything from men’s casual shirts to shorts in linen or cotton fabric.

Sneakers: Comfortable sneakers are always in style, but this summer’s seeing a lot of bright colors and bold designs. Shop around for sneakers with unique details, like contrast stitching or textured fabrics.

Utility-inspired pieces: This trend has been popular for a while now, but it continues to be a great option for the summer months. Cargo shorts, men's khaki shorts, hiking sandals, and vests with plenty of pockets are all great choices for a utilitarian-inspired look.

The key to summer fashion in Chicago is to choose pieces that are both practical and stylish. Breathable fabrics and comfortable footwear are essential, but don’t be afraid to experiment with bold prints and unique accessories to make your look stand out!


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