Chicago Winter Packing List

I’ve been relearning how to dress for winter after moving from Seattle, where ‘winter’ hovers around 40 degrees, to Chicago, where winter is negative temps and an ice cold blast of wind straight to your face. I’m learning all about the right fabrics, how to layer, and the importance of cold weather accessories (very, very important!)

For those of you visiting Chicago in the wintertime – there is still tons to do here when it’s cold – I’m sharing a Chicago winter packing list along with some outfit ideas. If you’re visiting, you’ll probably be doing a little sightseeing and spending time outside walking downtown or waiting for the L Train. You’ll want to pack plenty of layers, warm sweaters, and heavy duty coats. But, don’t worry, I also created this packing list to be chic and stylish as well.

Chicago Winter Packing List

Sweater // Whether wool, cashmere, or cotton, a sweater or two is a must for winter in Chicago. A v-neck style like this is definitely trendy right now, but a crewneck would also work. You can also use this as another scarf option by tying it around your neck. Or be like the cool girls and tie it around the waist over your coat. More affordable option here!

Turtleneck // A plain black turtleneck can be layered under your tops if it’s cold or you plan to be outside much of the day. I also think this is a chic top for a nice dinner when paired with jeans, ankle boots, and a wool coat.

Turtleneck Sweater // A second sweater option, this time in a turtleneck style. Having that extra bit of fabric around your neck makes all the difference, trust.

White Tee // I love layering my white tee under my sweaters for that extra pop of white at the neckline. I’m also apt to wear a base layer under my white tee with a sweater layered over top when it’s really cold.

Base Layer Top // A base layer top is absolutely essential for a winter visit to Chicago. I wear this one almost daily (I hate being cold) but this one is more light weight and works for mild winter days. While we’re talking base layers, you’ll also want to pack a pair of these.

Silk Top // I recommend bringing a nice top to pair with jeans or trousers for nice dinners (the food here is so good!). I love a silk top like this which is sophisticated and elegant.

Sweatshirt // For travel days or casual daytime activities, a sweatshirt like this is my go-to top. Throw your base layers underneath to stay warm.

Straight Leg Jeans // A pair of straight leg jeans (personally I think rigid cotton denim is the warmest option) is a versatile pair of bottoms that go really well with different styles of boots. If you like a full length jean (me too!), just be aware that the sidewalks can get slushy and dirty, and something more cropped will stay cleaner.

Black Jeans // A pair of denim in black (or a darker wash) is a good option for mixing things up. Black denim can also be dressed up for nice dinners or evening events.

Black Pants // A pair of nice pants with a stretchy waist (this pair comes highly recommended) can be dressed up for a show or evening event but is also comfortable enough for travel days.

Wool Coat // You’ll probably wear a puffer coat most days for treks outside around the city but a nice long wool coat is good for evenings, perhaps when you’re going to be taking a ride share instead of walking. Pair with a scarf, beanie, and gloves to keep warm.

Puffer Coat // I recommend a long puffer coat that covers your bottom and upper legs. It is so much warmer than one that’s cropped. I own this one and highly recommend it, but I love this one in this sand color and the faux fur on the hood.

Chelsea Boots // A thick soled waterproof Chelsea boot that has good traction is the way to go for daytime footwear. Obviously, check the weather – you may need to pack snow boots – but, IMO, these are so much easier to style. I own and love these shearling lined boots. And here is a more affordable option.

Ankle Boots // A pair of dressier footwear is nice for dinners or seeing a show. This pair has amazing arch support and works perfect for city walking (I can walk miles in these) but this is a more affordable option.

Accessories (don’t skip these!) // Beanie, Scarf, Evening Bag, Sling Bag (ASHLEYR15 for 15%off), Sunglasses, Belt, Gloves (and maybe some mittens, too!)

Chicago Winter Outfit Ideas

Below you’ll find some outfit ideas using the pieces in the packing list. I included a mix of casual outfits for daytime activities and more dressy outfits for evenings.

Shop My Chicago Winter Packing List

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