Layering in the Fall

Office Appropriate Outfits - Fall · You Pick Wednesday



First Row: Cowl neck Sweater | Crewneck Sweater | Sweater Vest

Second Row: Faux Fur Vest | Pants | Blazer | Blouse (similar) | Skirt

Third Row: Tights | Booties | Boots

Fourth Row: Gloves, scarf, hat, coat | Scarf, trench | Hat, gloves, coat, scarf


A reader recently asked if I could address the challenge of how to layer for the weather in Chicago.  If case you’re not aware, in Chicago the average highs for November and December range between 35 and 49 and the lows drop into the 20s.   Plus, it tends to be gray and windy.

With all that in mind, I pulled together some outfits using the pieces above with a few options for each temperature range.  I bet you can put together outfits from similar items in your own closets!






What to see examples of this in real life?  Check out Katie at An Alaska Weredork: A Style Diary.  Yes, she lives in Alaska and does a great job layering for the weather.




Don’t forget to submit your own questions, dilemmas or curiosities for You Pick Wednesday!

10 replies on “Layering in the Fall

  1. Bethany @ Accidental Intentions

    I love the handy-dandy coat guide you included in here haha. Last week I got yelled at by a co-worker for only wearing my fleece because it was “too cold” to be wearing just that as a coat (however, my warm pea coat was still in Michigan, so there wasn’t really much I could’ve done about it…it was the North Face or nothing), so now I’m all, “Crap. Is it too cold to be wearing my North Face? Or is it too warm to wear my pea coat? I DON’T KNOW!!” Haha. I spent nearly all of last winter rocking the North Face/sweatshirt combo since it never really got that cold (and I was still in college, so sweatshirts = totally acceptable. Not so much at work), which totally threw of my normal cold/coat perception 😛

    1. Erin @ Loop Looks Post author

      I’m currently wearing my leather jacket with a scarf most days. Laying a sweater or blazer underneath keeps me warm even though the jacket isn’t super heavy-duty. The peacoat will probably start making appearance shortly, though.

  2. Aparna

    Ahh, this post is much appreciated. I am yet to try the sweater under blazer combo. I doubt if only that will work minus the coat now that its almost low 40s? I cant handle cold very well..ah well thanks again .

    1. Erin @ Loop Looks Post author

      You can always layer more items or move up or down a group if you prefer to be warmer or cooler. So, if you like to be warmer you could dress like it’s in the 30s even when the highs are low 40s.

  3. Katie of Alaskan Weredork

    I love your outfit break downs, you’ve given me so ideas for layering down! (Any time anyone talks about cute winter ideas, I am there!) That furry vest in the last series is GORGEOUS, It’s amazing how warm that extra layer can be with those. And thanks for the sweet shout out, that was too kind of you! (Especially as your outfit break down are so much more in depth and better than my ramblings.)

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