My Love-Hate Relationship with Fashion During the Chicago Winter

During my recent 3 months of unemployment, I embarked on a clothes-buying sabbatical. We're talking shoes, bags, jewelry, belts, etc. - the whole shebang. Why? Simply put, I needed to save money and cut costs wherever possible.

It was a tough 3 months of not buying clothes because the silhouettes and shoes that are popular this winter a far different from that of last year's trends. Creating a somewhat updated outfit was even more of a challenge for me because, having lived only 1 winter north of the Mason-Dixon line, my wardrobe is still hardly suited for brutal winter weather.

Needless to say I was excited to finally secure a new job before the holidays, because that meant - shopping time!

Over the course of the past few weeks I have been working on creating a new business casual wardrobe. It sounds fun, right? - having a valid excuse to drop tons of money on clothes and accessories during the biggest sales events of the season. I thought it would be too; however, it's been nothing but stressful.

My three-month sabbatical made me forget how hard it is to find unique and affordable pieces that fit well on my not-so-averaged-shaped body. And trying to find shoes with heels that won't get stuck in between the wood planks on the train platforms (yes, this has actually happened to me before; my foot walks forward to step on the train when I realize my foot is bare all of a sudden and my shoe is stuck on the platform behind me) or fall into the grates in the sidewalk downtown (been there, done that; quite embarrassing, but more so, annoying), yet that are still business casual-appropriate and will allow you to trek safely through snow and across ice-slicked paths to client meetings, was quite the challenge.

Yes, I can wear my Ugg-like fur boots to and from work, but when I am walking from my office to meet a client downtown in the biting cold and snow, when I wouldn't dare wear my peep-toe heels, what is a girl to do? Waltz into the client's office in fur boots and attempt to inconspicuously attempt to change into your peep-toe heels? And then if you're successful, do you shove your wet snow boots into a large purse, thereby dirtying your appointment calendar and meeting notebook? Okay, maybe you can contain the wet boots within your purse in a plastic grocery bag; but then the question becomes: is it possible to carry a purse smaller than the size of a large child? And how ghetto do I look if someone sees me slipping fur boots into a plastic grocery bag?

These are serious questions, people, and I'm not sure I know the answers.