Olive and Fashion: Chicago Cyclone

Alright, let's do this. I love all the wonderful sites out there which I have bookmarked under my Daily Reads, Fashion, Shopping, and Inspiration folders. They truly help when I am trying to visualize what to wear the next day. As I lay in bed and begin to drift off, I can't help but to begin justifying Derek Lam's faux fur vest I was taunted with on style.com. I mean, it looks practical, I'll totally wear it when... when it's too warm for a coat but cold enough for a furry vest?

However, as a young savvy professional living in this Windy City, I cannot wear the whimsical DVF dress featured in September's Vogue or those new knee high boots I overnight shipped from Piperlime today. I had planned to wear something of this sort in my mind but I'm sorry, there are hurricane winds and rain storms on the way and I will need to dress appropriately.

Out come the Hunter rain boots (ok, ok I was dying to wear them anyway), the Anne Klein tote my mother oh-so-generously bestowed upon me in recognition of how necessary an organized yet very accommodating bag would be, and the pants. Which pants? I'm not sure yet. While visualizing my outfits I did not envision a possible cyclone which could elevate my skirt to embarrassing levels as I walk from the State/Monroe Red Line to the office on Franklin.

Here are a few statements I feel are fair enough to publish:

Chicago weather is unpredictable.
You check the weather app upon waking up, before you leave la casa, perhaps around/during lunchtime, at the end of your work day, and before setting the alarm for tomorrow morning.
Chicago fashion is not as outlandish as New York's or um... "liberal" as California's. I'd say it is a good mix, not ultra conservative but if you think skipping the classy factor in your outfit today is ok... think again.
Over the Knee boots are a great statement. But you don't want that kind of statement in the office so let's put them away until Hub51 this weekend.

Let's put together a quick outfit I can hop over puddles with, look presentable in my 10am meeting, and something which will allow me to sit Indian Style at my desk (because we all know this is the true comfort of pants). We must select an outfit consisting of pants which can be tucked into boots for the commute, layers on top for the cold wind and humid, a big bag to carry your work shoes and what nots (perhaps your 401K forms you forgot to bring yesterday), and of course warm and happy accessories because this is going to be a gloomy one.

Taa-daa! Chicago Cyclone Inspired Outfit for the commute...