What to Wear In Chicago | Winter Packing List

As winter arrives, many of us find ourselves traveling, whether it’s for holiday gatherings, weddings, or just a vacation. Chicago, in particular, is a favorite destination during this season. I recently visited Chicago for a friend’s wedding and learned a lot about what to pack for a winter trip there. From essential sweaters and jackets to durable boots, I want to share my Chicago winter packing list. It’s tailored to keep you warm and stylish as you navigate the chilly city. So, if you’re planning a trip to Chicago this winter, my list of winter essentials might just be the inspiration you need for packing smart and staying comfortable!

If you’re looking for more winter essentials, be sure to check out my Winter Capsule Wardrobe and my 6 Must Have Cold Weather Essentials as well.

Chicago winter packing list for winter

What to Wear in Chicago in Winter | Winter Packing List

Sharing my essential wardrobe pieces to pack for your trip to Chicago, as well as some chic outfit ideas! Also, for more winter packing ideas, be sure to check out my post here.

Chicago Outfit Ideas

Puffer Coat + Lug Sole Boots Outfit

Puffer Coat | What to Wear in Chicago in Winter

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A good winter coat is essential for braving the chilly winds of Chicago. And I’ve found that this long puffer coat from Mackage is a perfect choice. Mackage offers a range of stylish and warm coat options that are ideal for keeping you comfortable and fashionable during your Chicago travels.

Mackage long puffer coat

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I’m also a big fan of these lug sole boots. They’re not only comfortable for exploring and walking around the city but also keep your feet warm in the cold weather. A good pair of winter boots is definitely essential for traveling to Chicago this season.

Toggle Coat + Black Jeans Outfit

What to Wear in Chicago in Winter

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The toggle coat from Mango has become a staple in my cold weather wardrobe because it is not only stylish, but warm as well. I particularly love pairing it with black jeans, a cozy sweater, and black boots for a chic, put-together look. Plus, the Mango toggle coat is back in stock, so click here to shop it and here to check out some of my favorite ways to style it.

Black Leggings + Long Coat + Beanie Outfit

chic monochrome winter look

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For a classic winter look, I adore going for a chic monochrome look by pairing black leggings with a long black coat and black lug sole boots. To complete this outfit, add a cute beanie. I’m loving this striped one from Toteme, which adds a touch of elegance and warmth. If you’re a fan of Toteme like I am, don’t miss out on my honest review of the Toteme striped sweater.

Grey Joggers + Wool Coat Outfit

Wool Coat Winter Outfit

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When in Chicago, having a cozy and comfortable outfit is crucial, whether it’s for travel days or just a relaxed day exploring the city. I often opt for a monochrome grey look, pairing grey joggers with a matching sweater and topping it off with a wool coat. Then complete the outfit with Adidas Samba sneakers for added comfort. If you’re considering the Adidas Samba, be sure to check out my detailed review here for insights and tips.

Sweater Dress + Wool Coat Outfit

What to Wear in Chicago in Winter

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A monochrome grey sweater dress paired with a wool coat is my go-to for a winter outfit that’s both warm and stylish. The combination of a cozy sweater dress and a comfortable wool coat, finished with a pair of elegant boots, creates a chic look that’s perfect for anything from dinner with friends to exploring the city.

Cashmere Skirt + Sweater Outfit

Cashmere Skirt + Sweater Outfit

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If you’re in search of an outfit for a classy dinner or holiday event in Chicago, this cashmere sweater set is an ideal choice. It’s elegant, chic, and perfect for creating a sophisticated monochrome look. For more holiday party outfit ideas, be sure to check out my latest post here.

Wide Leg Jeans + Cropped Sweater Outfit

What to Wear in Chicago in Winter

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For an elegant yet casual ensemble, try pairing wide leg jeans with a cropped grey sweater, adding a touch of sophistication with boots and a stylish bag. My go-to bag is one from DeMellier, which perfectly complements any outfit not only this season, but all year around.

Black Puffer Coat Outfit

Black Puffer Coat Outfit

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A puffer jacket is an essential piece for your Chicago wardrobe, offering both warmth and style as the temperatures drop. For creative and fashionable ways to style a puffer jacket, take a look at my post here, where I share a variety of outfit ideas and styling tips.

Chicago Packing List for Winter

Chicago Packing List for Winter
Cashmere Sweater

Cashmere sweaters are a key piece for staying warm during Chicago’s winter, because they are both comfortable and stylish. They are ideal for the city’s cold weather, providing a cozy and soft layer, perfect for going under jackets and winter coats. I personally love this one from Reformation but they also have a lot of other great cashmere sweater options.

Sherpa Jacket

A sherpa jacket is another winter essential, perfect for keeping you warm in the colder months. I particularly love Mango’s sherpa toggle coat, but there are so many chic options to choose from as well. Check out more sherpa jackets here.

Puffer Jacket

This Mackage puffer jacket is my go-to in the winter months. It’s amazing quality and will keep you warm in any weather. Mackage coats are definitely a great choice if you’re looking for a jacket that is not only stylish, but great quality and perfect for the Chicago winter.

Lug Sole Boots

Lug sole boots are ideal for winter travel, because they are so comfortable for walking long distances, and they will also keep you very warm. For a range of stylish and practical lug sole boots, check out more options here, perfect for your next journey.

Comfortable Sneakers

Adidas sambas are my go-to for comfortable and stylish sneakers. They also come in a variety of different colors and styles, perfect if you want to match with all of your outfits. For inspiration on how to style your Adidas Sambas, be sure to check out my post here.

Jogger Set

A jogger pants and sweater set is an essential for comfortable travel, and opting for a cashmere set elevates your comfort even more. This set is not only cozy but also come in a variety of stylish colors, to inspire your next winter travel outfit. Also, if you’re traveling for work, check out my Travel Outfits for Work post for more stylish ideas.


Black jeans are a versatile wardrobe staple year round, but I personally love styling them in the winter, offering a chic alternative to classic blue jeans. These jeans from Reformation are a favorite of mine, and they come in a variety of colors as well.

Sweater Dress

A sweater dress is ideal for winter, offering warmth while keeping you stylish. It’s a comfortable and chic option for cold weather dressing. Opt for a chic grey sweater dress paired with a coat and boots for a Chicago look that will take you from exploring the city to dinner and beyond.

Tall Boots

Tall boots are a sleek and chic way to stay warm during the winter. They’re perfect for anything from a winter dinner date or a special event, adding elegance to any outfit. These tall black boots by Loeffler Randall are a favorite of mine because they are not only comfortable, but are so chic.

Suede Tote

I love incorporating suede totes into my winter wardrobe, and the DeMellier suede tote is a particular favorite of mine. Be sure to check out my Honest Demellier Bag Review for more insights on why I love this bag.

Black Leggings

Black leggings are an essential any time of year, but they are especially important in the winter for layering. They are also so easy to style. For some classy black legging outfit ideas for winter, check out my post here.

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Chicago outfit ideas for winter

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As always, thank you so much for stopping by today, I truly appreciate all of you! xx, Amanda


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