First off, you have forgotten everything you knew about fashion. And you said, the tight clothes will no longer do it. You're going to want clothes that lay against the body, rather than clothes that look like they were painted on.
There are some simple basics that will take you far. A nice pair of black dress pants is great-you can wear them to work, or you can wear them out. Express has a lot, and they are very flattering on everyone. Get a tan pair to wear with brown. Some of the stores will carry the kind of cloths that you are looking for it is the question of what kind of running around are you willing to do to have cloths that you want.
Look for the “Christie fit" because it has a bit of a younger look (so you won't look matronly). A black or grey pencil skirt is good to have too (again works for going out or work). Express has these, and you can actually find some nice ones at cheaper places. A crisp white button-up shirt is a MUST HAVE because it will ALWAYS be popular and look good. You can actually find some nice ones at most any store that you go to and again this will consist of you having to drive to many different stores so you can find the right one that matches you.
You'll also need a good pair of dressy jeans. My favorite brand is paper denim and cloth. . . they are ridiculously expensive, so I don't buy them in stores. Auction web stores are a lifesaver for stuff like this. Go to a store that has this brand (chip and pepper is good too). Try on a bunch to find your size. Then go onto a web store and search for the jeans you found. They usually have brand new jeans with the tags still on for less than half price. I don't know how they do it. But it is so worth it.
Well, you'll want more plain colored shirts now. H&M has great fitted long sleeve ones. Rich colors are in right now like plum and dark green. In addition to this, invest in a couple nice accessories-like a big structured bag or some chunky silver jewelry. They add a lot to an outfit.
The dress sounds great and you can wear it with either hose and pumps or tights and boots. Either way will look fabulous. If it were me I'd probably do the hose and pumps for the company dinner because that's the more conservative look, and wear the knee high boots for a dinner out with friends. Again, could go the other way too and still be perfectly proper! Enjoy the dress. . . it's so practical and at your height and weight, you probably look amazing in it!! I always recommend women have at least one of those in their wardrobe!
I am a huge fan of your idea of dark wash jeans and the sweater-personally I'd go with red or another bright color. The ankle boots sound cute. It's probably getting a little chilly for open-toed shoes anyway (I just live on the dangerous side). Any type of heels and jeans just looks so classy in my opinion. The cropped jacket sounds cute, as does the velvet pea coat. The jacket says “I'm such a fun gal!" and the peacoat says “I'm fun but much to classy!" so it is up to you. Both choices sound great.
Victor Epand is an expert fashion consultant at http://www.LingerieDress.com/ .