Preparing for My First Chicago Winter, Round One (and a polyvore!)

It’s already gotten pretty dang cold here in the Windy City.  The temperatures over the last two weeks have fluctuated slightly, but to me early October felt more like mid-December than early fall.  Each week it’s getting a little colder instead of a little warmer.

There are a few things I know about myself which make me very nervous about the pending doom that will be January, February, and March 2014.  First, winter isn’t that fun once the Christmas lights are taken down.  Second, I tend to eat a lot of comfort food, drink warm beverages, and stay indoors in the winter, which isn’t so great for the waistline.  Finally, if I don’t get enough sunshine in the winter months I can get a little mopey, which is most likely a mild case of that seasonal sadness thing.  Because these three things work together to make me feel not great, I need to do whatever it takes to be sure I am getting outside and getting some sunshine this coming winter.

So, I’ve been doing a little shopping.  Here’s what I’ve accumulated so far to keep me happily outside during the coming winter months.  I’ve used Polyvore to piece together pictures of the items I’ve purchased, and while this effort is notably awkward and slightly unfortunate, this month is all about trying out new things on the blog!    So, I’m sharing my recent shopping adventures AND this sub-par photo-collage with you.

1.  Down Coat

Everyone I’ve met here in Chicago has recommended that I get a down coat immediately.  After a bit of research, I decided that the Lands’ End featherlight down jacket would be my first investment piece.  What I like about this coat is that it is incredibly light weight, it’s rated down to -10 degrees, and I can push the sleeves up or layer a lot underneath it without feeling bound up.  Also, I got it on sale for only $69.99 when the comparable coats from other stores were more than twice that cost.

2. Gloves

For gloves, I chose the Lands’ End EZ Touch casual gloves in Vicuna, which is a soft brown color that slightly contrasts my coat.  They aren’t waterproof, ski-quality gloves, and they aren’t fancy leather gloves, but for reading my phone while waiting for the bus this winter I think they will be just right.

3.  Scarves and hats for warmth, not just cuteness

I have a ton of cute scarves, but they are typically lightweight and not really made for keeping warm.  I added two winter scarves to my collection from Lands’ End sales, and while the red-and-white will be adorable during Christmas, the CashTouch scarf is also very nice and I might order a few other colors if I need them later in the season.  I also picked up the red-and-white hat to match my new scarf, because I don’t have any winter hats and really need to build that part of my wardrobe.  The red-and-white set was on super clearance and I was able to get a great deal.

4. A medium-weight fleece for layering

For a cozy intermediate layer, I also picked up an L.L. Bean sweater fleece.  It’s incredibly warm and looks nice enough to wear in the office if I need it.

Winter Essentials Round Oneb

If you’re on the market for affordable winter wear, I really cannot recommend Lands’ End enough. You have to be careful to avoid the granny-styles, but if you take some time to weed through their products, I think you’ll find that the quality and affordability is fantastic.

Do you have any winter must-haves to recommend?  Tips for surviving the cold weather?  If so, please share them here. 



  1. Meagan

    As someone who grew up where you did and now has to deal with harsh winters also, here are my pieces of advice:
    1. snow boots. I have North Face boots that look relatively nice for what they are, but they are a must!
    2. Keep a pair of shoes at your office if you don’t want to wear snow boots all day. Sometimes I just wear my snow boots all day anyway because they are so nice and cozy.
    3. SmartWool socks and tights. They are thinner than your average wool socks but just as warm.
    4. In addition to the fleece and down coats (Lands’ End IS awesome for that) I also got a heavy winter coat from them, rated to -40. It is fantastic and I don’t know what I would do without it some days! BTW, it can get below -10 in the winters in Chicago (usually a couple days per year), especially with that darn lake!
    5. You might need heavier gloves than the ones shown for those occasional really cold days. Mittens are warmer than gloves. Sometimes I layer a thin pair of gloves under big mittens.
    6. Keep lotion with you. The colder it gets, the drier it gets.
    7. Don’t worry about being cold all the time. Yes, it’s cold, but honestly, once it gets to a certain level, it doesn’t feel any colder even if the temperature keeps dropping. Also, and my husband who is from Wisconsin agrees with this, 30 degrees in Tennessee feels colder than 30 degrees in Wisconsin. I imagine it’s the same in Chicago. :-)

    • pink-briefcase

      This is SO HELPFUL, thank you so much! Everyone has been saying SmartWool socks, so they are definitely going on my shopping list, and so will everything else you’ve mentioned here.

  2. accidental devotional

    Long Underwear. The nice thin silky stuff. Seriously. Oh and tights. Even under pants because that works. (I abandoned the mid-west for the south and couldn’t be happier about the weather. Good luck friend.) Also, even on cloudy days you can get the light you need, so stay outside as much as possible.

  3. Pingback: How to Survive the Coldest Winter Ever (Round Two) | pink-briefcase

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