What to Wear in the Bitter Cold (See Jane Freeze)

hat / infinity scarf / coat / jeans / shearling-lined boots
boot socks / lined gloves / turtleneck 

Winter in Chicago is not for the faint of heart.  When the temperatures drop below zero and the wind chill is upwards of -50 degrees, it’s hard to think of fashion when all you want is to keep warm.  You know it’s truly cold when any exposed skin simply hurts when you go outside (hint: use a scarf to cover your face up to your eyeballs).  A few more of my tips of surviving this brutal winter weather:

1.) You can avoid puffer coats by taking advantage of the whole “oversized” coat trend.  Why?  You can fit more layers underneath that will keep you warm!
2.) Wear thick socks–even if wearing low booties.  (I know lots of people who forego socks with their UGG boots or if they’re booties are low-cut.)  If it’s truly cold and you’re walking around outside, you will regret any exposed skin.  Frostbite really happens!
3.) Hats and gloves are crucial.  I know this sounds obvious but street style pictures often depict stylish people with unzipped coats, exposed ankles and no gloves; frostbite is never in fashion.
Stay warm!


  1. Winter in Chicago has been crazy. This is coming from a person who has been a Texan her whole life up until recently. Thank you so much for your tips! The oversize coat trick is absolutely brilliant, and so simple. I can't wait to put one to good use, and stack myself up in layers to keep warm.

  2. Great tips; I've come to find out myself that an oversized coat + plus some sort of jacket/sweatshirt really makes a difference. Oh yeah and wear like 3 pairs of gloves too! Stay Warm! xx

  3. most definitely not for the faint of heart. it is absolutely freezing down here in kansas city and i know it's even colder for you! when it is this bad i just do not even care about looking cute anymore, it's just about staying warm enough.

    i have found that bright beanies and fun socks that peek over my boots help me feel a little less like a plain black marshmallow though!

    stay warm!

    xo mary-katherine

  4. I'm totally guilty of wearing low socks with ankle boots but it's actually your site that made me realize socks with booties and cropped pants can look super cute! And in NYC recently, it's been totally necessary to cover up all exposed skin. So thanks!

  5. I live in Canada and the best defense against the cold is:

    1. Goose down parka (a real one, not a stylish one that looks like goose down but isn't)

    2. Cashmere sweater underneath that

    3. Fleece-lined leggings

    4. Pantyhose underneath your pants

    5. Warm insulated rubber boots (Sorel for instance)

    6. Cashmere wrap for your face

    7. Cashmere beanie

    8. Thick cashmere / shearling gloves

    .. and that's how I stay warm.

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