Teacher Fashion: What's really necessary?

As I begin prepping to purge my closet of all unnecessary items (a biannual tradition here in Casa del Blanco), I wonder what really are the "must-haves" as a teacher? I know it's very different for elementary school teachers, who more than likely come home splattered with this or that, or those who teach specials or exploratory classes, so what about specifically middle and high school teachers?

I would love to be the type of person who has a "ten" piece closet, but since I live in reality, and frequently daydream about turning the extra bedroom into a giant walk-in closet, I'm going to check myself, lest I wreck myself.

At the beginning of the year I said to myself, "You are going to wear every single item in your closet." Ha. That so did not happen. The school year started, the stress came on, and with that, the laziness kicked in big time. I think I've been rotating the same five or six outfits, throwing in a casual Friday and a spirit wear Monday in as often as possible. When I walk into the closet though, I know that I have spent a lot of my paycheck on what's inside this little fashion palace, so I should stop being lazy and put an outfit or two together!

However, do you ever feel like you are in a fashion rut? I frequently feel as if I wear the same "type" of outfit almost every day. When you live in the Chicagoland area, or anywhere where the sun disappears for months at a time, it's not really fun to get up and contemplate putting on something adorable when you know you will be also adding a parka,  snow boots, a scarf, gloves, hat, and packing your other shoes to put on once you get to work. Winter has a tendency to kill fashion around here, at least for me.

So what's doable for teachers when it comes to fashion?

I have some needs, I'm a little picky when it comes to what I wear, and this is what I would say to a stylist if I could ever afford one:

1. I generally avoid button downs unless I have a sweater on over it... I teach middle school, I can't see all the buttons on my shirt due to my body type....use your divine inferencing skills.
2. I don't like the whole Pinterest "put on fifty layers" trend. I'm trying to decrease bulk, not add to it! I don't know about you, but teaching all day keeps me pretty warm. I don't want to look like the stay-puft marshmallow man when he's angry by 9th period. 
3. I want to be comfortable. I don't want to be pulling or adjusting my clothing all day. 
4. I have an unhealthy obsession with leggings and ballet flats that I completely blame on Audrey Hepburn. I'd wear black ankle slacks, but the button came off and I haven't sewed it back on yet. (It came off two years ago...again...lazy).
5. I would dress like it's the 50's or early 60's every day if I could. However, I dressed in my cutest retro outfit one day a few years ago and a kid asked me why I was in a costume. Confidence balloon=popped.
6. I feel like I have the shortest neck in the entire universe. It bothers me a lot, and I just felt the need to share that I'm sensitive about it. Thanks for listening. 
7. I'm short. 5'0. Nothing looks like it does on the mannequin on me. I'll either look like Frodo in Legolas' clothing, or an exploding cupcake. Yikes.
8. On that same note, I'd like any outfit I wear to make me look at least between 5'2 and 5'4 and 20 lbs. lighter, ok?

So what's a girl to do but turn to the blogiverse for answers? What are your favorite fashions? What are your struggles with dressing for work? How do we prevent ourselves from falling into fashion ruts? Who are your style icons? What era is your favorite?

On another note, I religiously watch blogs where people do Stitch Fix. Does this work? Have you had success with it? Please sound off and share your experience! :)