Your Guide on What to Wear and How to Survive a Chicago Winter
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  • Writer's pictureBrenda

Your Guide on What to Wear and How to Survive a Chicago Winter

Winter in Chicago is a magical time, with the city adorned in snow and a festive atmosphere filling the air. However, the Windy City's temperatures during the winter months demand both warmth and style.

In this blog post, we'll explore 11 chic outfits that will keep you cozy while looking effortlessly fashionable during the chilly Chicago winter. If this is your first Chicago winter, you want to keep reading as I’ll go through some must-have winter items to invest in.


*Disclosure: This post may contain affiliate links, which means that I get a small commission if you decide to make a purchase through the links, at no cost to you.

What to Wear in Chicago Winter

1. Classic Trench Coat and Scarf:

A classic trench coat paired with a cozy scarf is a timeless combination that exudes sophistication. Choose a warm, woolen scarf to keep the chill at bay while walking along the iconic streets of Chicago in the cold weather.

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2. Puffer Jacket and Beanie:

Embrace the warmth of a stylish puffer jacket paired with a matching beanie. This casual and trendy look is perfect for navigating the city's winter wonderland. With the average temperature hovering at just below freezing, keeping your ears warm is a good idea.

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3. Camel Coat and Knee-High Boots:

A camel coat adds a touch of elegance to your winter wardrobe. Pair it with knee-high boots for a chic ensemble that keeps you warm and on-trend. This look is a great option for dinner at some place downtown Chicago.

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4. Faux Fur Vest and Leather Leggings:

For a fashion-forward winter look, consider a faux fur vest layered over cozy knitwear like a cute turtleneck. Combine it with leather leggings for an edgy touch that stands out against the snowy backdrop.

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5. Oversized Sweater Dress and Tights:

Stay cozy and stylish this time of year in an oversized sweater dress paired with opaque tights. Add ankle boots and a woolen hat for a chic winter ensemble that's both comfortable and on-point. A winter coat would be necessary if you’re going to be out for long in the cold temperatures.

Get the look HERE

6. Wool Turtleneck and Wide-Leg Pants:

A wool turtleneck is a winter wardrobe staple, providing both warmth and style. Pair it with wide-leg pants made from heat-trapping materials for a sophisticated look that transitions seamlessly from day to night. Add a warm hat if it’s going to be particularly cold.

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7. Plaid Coat and Skinny Jeans:

Bring a pop of pattern to the winter streets of Chicago with a stylish plaid coat. Team it up with skinny jeans and ankle boots for a modern, city-chic vibe. Opt for snow boots if the weather forecast calls for snow or if there’s already some on the ground.

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8. Long Cardigan and Over-the-Knee Boots:

Layer up with a long cardigan and complement the look with over-the-knee boots. Complete your look with a long line coat to face the low temperatures. This cozy ensemble strikes the perfect balance between comfort and fashion, perfect for a day out in the windy city.

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9. Quilted Jacket and Corduroy Pants:

A quilted jacket is both practical and stylish for tackling winter in Chicago. Combine it with corduroy pants for a textured and warm outfit that's perfect for exploring the city. Your base layer could be a thermal sweater to ensure extra warmth.

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10. Monochromatic Knitwear:

Opt for a monochromatic look with matching knitwear. A sweater and pants in the same color create a sleek and streamlined appearance that's ideal for a winter day out. Complete your look with sleek knee boots. This outfit is a great choice for a walk in Millenium Park.

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11. Sherpa-lined Parka and Snow Boots:

When the Chicago winter turns frosty with a high wind chill factor, a sherpa-lined parka and snow boots become essential. Stay warm and stylish as you navigate the snow-covered streets with this cozy ensemble.

Get the look HERE

Braving the Chicago winter in style is all about finding the perfect balance between warmth and fashion. These 11 outfits offer a variety of chic options to keep you cozy and on-trend as you explore the cold climates of the Windy City.

So, bundle up, embrace the chilly weather, and showcase your winter fashion flair on the iconic streets of Chicago.

Chicago winters are renowned for their chilly temperatures and snow-covered streets, making it essential to be well-prepared for the elements.

Get the look HERE

Now that you know the best way to stylishly dress for the winter we'll explore 10 winter essentials to own or add to your Chicago packing list. These items will be essential for a comfortable and stylish experience during the frosty season in the Windy City.

Chicago Winter Essentials – A Guide

1. Insulated Parka Coat with Hood:

Invest in a high-quality insulated parka with a hood to shield yourself from the biting cold winds that Chicago is known for. Look for one with additional features like water resistance to keep you warm and dry.

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2. Warm Winter Boots:

Navigating snowy sidewalks requires sturdy and warm winter boots. Opt for a pair that is both waterproof and insulated to keep your feet cozy and dry in the snowy conditions. Ugg boots are a popular choice as they are made for harsher winters.

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3. Thermal Layers:

Stay warm by always adding a thermal layer to your winter outfits. Thermal tops and leggings provide an extra layer of insulation under your winter attire, ensuring you remain comfortable and maintain your body temperature in the chilly weather.

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4. Touchscreen Gloves:

Want to keep your hands warm while staying connected? The best way to do so is with touchscreen gloves. Look for a pair that allows you to use your smartphone without exposing your fingers to the cold.

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5. Wool or Cashmere Scarf:

A wool or cashmere scarf is not only a stylish accessory but also a practical one. Wrap it around your neck to add an extra layer of warmth and protect against the chilly Chicago weather.

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6. Insulated Water-Resistant Gloves:

Invest in insulated and water-resistant gloves to keep your hands warm and dry in the snow. Look for gloves that offer both insulation and protection against moisture. They don’t have to heavy duty to do the trick.

Get the look HERE

7. Thermal Socks:

Ensure your feet stay warm with thermal socks. This is especially true if you plan to be in the cold for extended periods of time, checking out attractions such as Lincoln Park.

Thermal socks such as wool socks are designed to trap heat, providing additional insulation for your feet during the coldest days of winter.

Get the look HERE

8. Snow-resistant Trousers:

Opt for snow-resistant trousers or insulated pants to keep your lower body warm and dry when walking through snowy streets. These pants provide protection against the winter elements. For extra warmth, add a pair of long underwear or fleece-lined leggings underneath.

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9. Beanie or Ear Muffs:

Keep your head warm with a cozy beanie or a pair of ear muffs. These outer layers are essential for retaining heat and protecting your ears from the cold winds in the winter season.

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10. Hand and Foot Warmers:

For exceptionally cold days, consider carrying hand and foot warmers. These small, disposable packs can be tucked into your gloves or boots for added warmth during extended periods outdoors.

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Equipping yourself with these 10 winter essentials ensures you're well-prepared to face the challenges of a Chicago winter. From insulated parkas to thermal layers and snow-resistant accessories, these items will not only keep you warm but also help you embrace the winter season with style and comfort.

So, gear up, stay warm, and make the most of the snowy wonders the Chicago area has to offer during the winter months.

As the Windy City transforms into a winter wonderland, choosing the right footwear becomes paramount for navigating the chilly streets of Chicago. From snow-covered sidewalks to icy patches, having the right shoes ensures both style and comfort during the frosty season.

Get the look HERE

Below, we'll explore the 7 best shoes to wear in Chicago winter, providing the perfect balance between practicality and fashion.

7 Shoes to Wear in Chicago Winter

1. Waterproof Snow Boots:

Investing in high-quality waterproof snow boots is essential for facing the unpredictable winter conditions in Chicago. Look for boots with insulated lining to keep your feet warm and a durable, slip-resistant sole for navigating snowy and icy surfaces.

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2. Insulated Winter Sneakers:

For those who prefer a sporty and casual look, insulated winter sneakers offer a comfortable and stylish alternative. Choose a pair with thermal lining and water-resistant features to keep your feet dry and warm.

Get the look HERE

3. Tall Leather Boots:

Tall leather boots are the best option to not only provide a chic and sophisticated look but also offer excellent protection against the winter chill. Opt for insulated options that cover your calves to keep you warm during cold days.

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4. Waterproof Ankle Boots:

Ankle boots are versatile and stylish, and when they're also waterproof, they become a practical choice for Chicago winters. Pair them with warm socks and leather gloves for added warmth and a fashionable winter look.

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5. Shearling-Lined Booties:

For a touch of luxury and warmth, shearling-lined booties are an excellent choice. These cozy and fashionable boots provide insulation while keeping your style on point during winter outings. Pair them with puffy coats for chic yet warm everyday wear.

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6. Insulated Chelsea Boots:

Chelsea boots are a timeless and versatile option, and when they're insulated, they become a winter essential. Choose a pair with a waterproof exterior to combat slush and snow.

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7. All-Weather Sneaker Boots:

Blending the style of sneakers with the functionality of boots, all-weather sneaker boots are perfect for the dynamic winter conditions in Chicago. Look for options with durable soles, water-resistant materials, and thermal insulation for optimal comfort.

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Navigating a Chicago winter requires footwear that combines style, durability, and practicality. These 7 shoe options cater to various preferences, ensuring you can step out in comfort and fashion during the frosty season.

From waterproof snow boots to insulated sneaker boots, embracing winter in Chicago becomes a stylish affair when you choose the right shoes. So, lace up, step out, and make the most of the snowy wonders that the Windy City has to offer during the winter months.

Get the look HERE

Do check out my post: 11 Shoes to Wear with Dress Pants in the Winter for some ideas on how to style your dress pants for the cold.

I also have a post titled: 7 Shoes to Wear with Dresses in the Winter, which shows you the perfect pair of shoes to pair with your winter dresses during the colder temperatures.

Until the next post,



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