k, Citrus: you moved along faster than I could answer, but ballet slippers come in high end leather (I wear the ALL the time) to 6 dollar fabric ones at accessory stores. You can get them in metallic (silver is big for fall, btw) and they go great with jeans. I like the simple black ones with capris (think Mary Tyler Moore in The Dick Van Dyke show). I'm in my mid 40s and they look so much better than crocs, flip flops, or sneakers! You always look polished with a little shoe. Round toe is the cutest, but if you want to elongate your leg, a pointed end is nice too.
Pointy shoes... I'd go for a slight pump. I don't like the really really pointy ones, but if you don't like them you can go for a more round toe although it's something more suited to younger women. The lace up spat look (high heeled) is pretty cool this fall season. I'd wear them with a pair of pants, a white shirt left out and a vest. Vests are REALLY in this year. You could even wear the school boy look and have a tie loosely around the collar... not tight... Annie Hall. The pants are also a bit looser for this look.
and Citrus, yeah, I'm a triangle. My butt is in the plus store my tops are in the fun ones. Sigh.
Sandy: Emerald green silk is the BEST with red hair. I used to be a redhead and it was my one blouse that really garnered the compliments. Try one of the new high-waisted skirts, in a textured or lovely fabric with a teeny belt on the skirt. Very 40s and classic. Suits with the blouse work well, too as they often look too severe and the green will pop. Slouchy, pleated high-waisted pants would look great with these too.
Note on nails: the look now is natural, not fake nails. Cut to be roundish, just a bit of white showing and buffed, not coated with goo. Also a really simple pink or beige-y pink for professionals is best.Depending on where you work, you might want to save the blue nail polish for your toes. And never match your toenails to your fingernails.
Skinny jeans: gotta be tall and thin to pull these off well. They are really hot right now as are wide legged jeans too! (thankfully). The key is to wear them so they don't make your body look like it goes from wide to a point (like you're teetering on your pins) If you're straight up and down, then they're fine. Tucking them into boots looks fine if you're under 35, but over that and you look like you're waiting for a John. Really. Also, unless you're in your 20s and thin as a rail (or teens) no wedge boots with this look. crepe soled boots add pounds to the look.
Black is so slimming but dull. Pop it with jewellery, scarves, lovely shoes and lipstick. I actually love seeing a well-dressed goth look. But note the over the top lips and eyes. Very cool and striking (of course, not for work, but I like to look at it)
I also thought about collars today. Giving a bit of 'lift' to your collar (no not like Elvis's) makes an older neck look softer and you look sophisticated. If your fabric can be starched, iron it with starch, open so you can mould it into a face framing look. I have one that's a bit too floppy, so I sewed some interfacing into the inside of the collar and that worked. Really tricky if you can't sew, might not be a good venture.
Diemde: What are you going to be doing in Chicago? professional? evening out? tourist? An amazing look is the jean, blouse (untucked) with a very well pressed and folded sweater over the shoulders and loosely tied, great sunglasses (the larger ones), gold jewelery. You can fold up the sleeves of this shirt and could show off a big bangle bracelet (easy on the size of the necklace if you do that). This would be a good tourist/shopping look. And get an large bag, something funky.
Suits can look stodgy. Break them up. Buy a really lovely rust-coloured jacket to team up with some earth tones (i've seen your pics). This can go with chocolate trousers and some ankle boots. Pagminas over blouses and jackets will make you look rich and important. These come in every colour known to man and can give you the bright glow you might need. Don't worry about being 50. Just don't dress like you're 20 and you'll be great.
Hair... I think a great and easy cut on you would be parted on the side, shortish, but long enough in the back to flip it out. It will lift your face without surgery! And if you can, invest in some new, cool glasses. You will ROCK!