How to Create a Wardrobe for Chicago Winters

Bundle up in Chicago for the winter (especially with that lake effect snow).

Chicagoans like to joke that if you don’t like the weather, just wait a few minutes. Corny, but true. Weather can shift dramatically between Uptown and Downtown, from the West Loop to East Lakeview, which can make getting dressed a confusing chore. Knowing how to dress for a Chicago winter is a rite of passage for new residents and a badge of honor for current Chicagoans, and it’s about more than just a warm coat. Read on to learn how to stay warm, dry, and stylish for all parts of the Chicago winter. 

Layering 101

There’s an art to dressing for Chicago winters, and it starts with a solid foundation of layers. Because the temperature can dip and spike within hours, or between L stops, layering allows for maximum comfort with minimal bulk. When it comes to base layers, the best fabrics are made from synthetic wool, silk, or bamboo fibers because they trap warmth well and wick away moisture. Avoid cotton, which takes too long to dry and pulls heat away from the body, leaving you clammy and cold. To avoid being too puffed up, look for fibers, like merino wool, which can be both warm and relatively slimline. 

The basics 

Let’s get the obvious out of the way. You’ll need a solid coat, durable shoes, and some good ‘ole common sense to get through an (in)famous Chicago winter. And if you think toughing out negative-degree weather in shorts and t-shirts is some kind of trophy, well, you’d be wrong. Why be cold when you can be comfortable? 

When it comes to your coat, fashion should complement function. You don’t want your coat to be too snug or you’ll be a bucket of sweat after a subway ride or a brisk walk to the office. The best models are breathable, wind-resistant, and allow for free movement in your arms and shoulders. Keep in mind: 

  • Water-resistant is key, as most winter weather is a mix of rainy snow or snowy rain, thanks to the beautiful lake next door. 
  • Look for a coat with a hood that stays close to your head, which keeps the body heat in and the wet weather and wind out.
  • A decent winter coat is a good investment, so it’s best not to scrimp on durability, flexibility, and comfort. A classic mid-price synthetic down option will see you through several years as a comfortable commuter coat. A more expensive full-down option, like Canada Goose, will certainly keep you warm but might not be economical for your lifestyle and usage. Shop around, including neighborhood boutiques, to see which options best fit your budget and your lifestyle.

Chicago winters are long, slushy, and wet. Durable, waterproof, winter-ready shoes can make your commute lovely or loathsome. Here are some things to consider for footwear: 

  • If you plan to do some urban hiking in the winter months and need the best traction, warmth, and support, consider tough-soled winter boots, such as KEEN, Merrill, or Sorel brands.
  • If you have a short but wet walk to and from the CTA, or want a lighter pep in your step, a good pair of rain boots, like Hunter or Sperry, might be better suited to stay dry without added heft. Just add thick socks for a cozy fit, and make sure the boot comes up tall enough to protect from any puddle sloshing. 
  • Look for products that are waterproof, not just water-resistant, and ideally have a lug-soled bottom and warm interior lining, such as brands like LL Bean’s famous duck boots. 
  • Make sure your winter socks are made of a tight weave and moisture-wicking material, such as merino wool. Compression socks also help keep blood flowing to your lower limbs.
  • Commuter tip: If possible, keep work-appropriate shoes and socks at your office, either tucked into an empty cabinet or stashed under your desk. It’ll be one less thing to schlep around, plus professional footwear is a more polished look in the office. 

The accessories

When it comes to winter accessories, stock up on several pairs for any occasion so that you are prepared for the slush, sludge, and snow.  

Cover your head with a nice weave and a cozy interior, such as fleece, shearling, or silk (especially if you want to keep frizzy hair at bay). Earmuffs and headbands work to cover your ears, but full-head coverage is best for keeping your noggin warm in the chilly winds. Now that Bluetooth technology is available in many hat styles, you can stay warm while listening to your favorite podcast. 

A pair of washable insulated slimline gloves for everyday wear from brands like the North Face, Lands End, and Under Armour keep fingers toasty and agile for holding coffee and reaching for your Ventra card. A text-friendly style and thermal lining are a nice upgrade for fashionable dexterity. It’s also nice to have a few of the cheap, stretchy gloves on hand (pun intended) — they’re great for layering under big mittens for especially windy days.

Anything that blocks the wind, covers your face, and is washable is a good buy. A rechargeable heated scarf might be worth exploring if you have a chilly office and a lengthy commute, and a colorful pashmina adds functional fashion to your office attire. 

You won’t get chilled to the bone in fleece-lined leggings and long underwear. Opt for soft fibers like silk and bamboo with a comfortable fit so air can move freely. If your job requires more formal business attire, wool tights or flannel-lined pants can add the extra layer of warmth and coziness through a day of meetings. 

Armed with a warm coat and these tips, you’ll handle this Chicago winter like a pro! And the less you’re worrying about freezing toes or a wind-burned face, the more you’ll be able to appreciate the beauty of the city in this season.

Bonus: Where to Shop

Visit any of the following Chicago locations for name brand and local creations. 

Macy’s: It’ll never be Marshall Field’s, but it is still a classic State Street destination, with name brands and excellent customer service.

Fleet Feet: Locations in Old Town, Lincoln Square, Lakeview, and South Loop, as well as a handful of suburbs locations, means that this premier running shop knows the ins and outs of the outdoor elements. 

Alice & Wonder: A women’s boutique in Lincoln Park and on Southport has a wide range of cozy knitwear items, as well as outerwear and accessories. 

Carhartt: Seriously durable and utilitarian (and now, trendy), this Wicker Park storefront is no-nonsense about quality items. 

Penelope’s: This Bucktown staple has a rotating variety of trendy warm weather hats, sweaters, and accessories. 

Art Effect: A Lincoln Park boutique hosts a funky and charming array of winter accessories and gifts.

REI: The Lincoln Park flagship store (and its four suburban outposts) has plenty of options as well as knowledgeable staff. 

Gearhead Outfitters: This Lincoln Square shop boasts everything you need for outdoor adventures and has North Shore locations.

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