Working Girl

Guess who starts her first big-girl job on Monday?!
I've been waiting to announce it for a while, but have been biding my time meanwhile trying to figure out the perfect first day outfit (because, priorities), creating all sorts of contingency plans for anything that could possibly go wrong, and not thinking about how I no longer get any breaks unless I plan them. Also, somehow I've made it this long without owning an iron, which I'm thinking probably needs to be rectified. But do I get an iron or one of those fancy steamers? (#firstworldproblems)
I really enjoy these and already have a khaki skirt, but there's the constant nagging worry that I'll look like a schlump because of my figure and height. Also, sorry, random girl, for putting your picture on my blog. As I've never had the need for them previously, I have a distinct lack of "work staples" in my closet, but I'm trying to focus on just first day for now, because I'm not too sure on what the work culture is like re:clothes, and will probably have to adjust accordingly.
I don't know when I got so modest, but I have been in the market for some really good below-the-knee, slightly-flared/A-line skirts for months! They are a little problematic to wear in the winter, which is a bit of a downside (unless anyone has tips for that), but otherwise, I would be all up on this outfit. It looks so comfy!
And finally, I guess I have to get some pants and probably some blazers. I love this color, and love the cropped pants trend, but am not excited about trying to find things that I don't have to have tailored.

What are your work staples? Where do I find them where my poor, broke ass doesn't have to shell out an arm and a leg? Help, I want to dress like Blair Waldorf!