I am in Chicago too, and I have a couple of different winter coats to resolve this issue. I have a medium-length toggle coat and long dress coat, both of which will fit over a blazer/suit jacket. I also have other medium and heavy weight shorter, more-fitted coats that I wear on days when I am not wearing jackets underneath.

I've learned in 19 years of living out here that having only one winter coat isn't enough, unfortunately! :)

Thank you Kristen, for the advice. I grew up in Louisiana and just moved to Chicago this year. I didn't even own a winter coat until October! This is all so new to me.

i'm from the midwest as well (milwaukee), so i can totally sympathize with the winter weather. i was actually in evanston, il on sunday, and i couldn't believe it was snowing!! it worked its way up to milwaukee that night though...grr...

anyway, back to the question at hand! multiple jackets may be the way to go. perhaps buy one that works specifically for blazers underneath and another for days you don't wear a blazer. you could also buy a jacket with a detachable liner - that way, you have a lightweight trench for the spring to wear with blazers and a warmer coat to wear w/o a blazer underneath during the winter.

you may also want to consider wearing cardigans, which can still help you achieve a pulled-together look without adding much bulk. also, pullover sweaters over a button-down shirt would look nice too.

Have a look at this blog post:

http://youlookfab.com/2009/02/.....manhattan/

Thanks everyone for the great advice!

If you have anything more than delicate shoulders and arms, then you will be wise to wear a jacket while trying on coats to ensure that you can wear jackets under the coat.

I have only one winter coat that works over jackets; the rest are too fitted in the shoulders. That coat is a black, stylish puffer with a shawl collar. Something about the cut of it works over bulkier layers. My Jcrew and other wool coats? Too fitted in the shoulders - and the arms too (my upper arms are kinda bulky - or perhaps they are "average" - I just know they aren't thin.). (Actually my cream puffer would probably also work, but I'd completely overheat, since it's super-warm and keeps me cozy even with just a flimsy blouse on and no other layers).

If you do size up for more room in the shoulders, be sure that the coat works vertically (waist hits where your waist is; hemline isn't too long, etc), and not just horizontally.

A coat with shoulders like this:
http://www1.bloomingdales.com/.....ageID=4371*1*24*-1*-1*8

Is going to provide more room for a blazer than one like this:
http://www1.bloomingdales.com/.....ageID=4371*1*24*-1*-1*12

The photos are great! Thank you for the ideas - I'll be sure to hit the coat clearances going on now and stock up for next winter. I'm a bit of a cold weather novice, so details like the shoulders are a huge help for me.