Thanks for the comments! Here's an update if any of you all are interested (long post, sorry):
I got a little more detail from her today when we met and she wants to start dressing more nicely to work because although pretty much everyone wears jeans and a t-shirt (she works in tech), it was brought up in a review of one of her coworkers that the management thought her coworker dressed inappropriately for work (too casually). My friend is going to be moving buildings and will be sitting closer to management, and wants to make a good impression. This is a good reason, because I think it will drive her to keep at it.
We started by me asking her what her favorite outfit in her whole closet was, and why it was her favorite. This was helpful, because we figured out that she likes open necklines, and she likes her clothes to be comfortable. And then I asked her to pull out a "nice" outfit she would wear to a meeting with a boss or something. For this she pulled out some brown jeans and a long sleeved teal v-neck t-shirt with a built in cami. So we talked a little about how she felt about this outfit, and what she might be able to replace it with.
The khaki pants were actually okay, welt pockets, and they had shaping and were a good length (ppl), and she had a pair of darkish denim that had ppl and fit her okay, so we decided to focus on tops for this shopping trip, since a lot of her shirts were boxy and unflattering. We figured out that she actually has a very small waist, and that she is a pretty pear that tends toward an hourglass. She is also short waisted. She seemed to think she was a lot heavier than she actually was, and so she wore loose clothes to "cover it up." So I sort of suggested some shirts that I thought would work, ie shirts that were tailored and came in on the sides, but had ruching or draping, or possibly an empire waistline with a flat front to hide her little tummy she had. She liked the idea of that, and so we went to NY&Co and we got this shirt:
http://www.nyandcompany.com/ny.....=cat350008
in the dark brown, since she doesn't like a lot of color. I thought I would introduce that slowly. Everytime I suggested a bolder cool jewel tone (which looks really great on her) she would sort of shy away and say she'd never wear it. So we stuck with the basics for now. I hope the shirt was a good choice for her body type. I thought it looked really cute on her, and she liked it as well. We are planning on finding a great jacket to wear over this top.
Then we went to AT and shopped the sale rack, and we got her a couple of longer V-neck knit tops with long sleeves in blue and one in red (she's picky about what shade of red she likes), and a navy and white printed sleeveless top she really likes, and this, which is my favorite shirt because it just looks like "her" and fit her really nicely:
http://www.anntaylor.com/catal.....ory=Misses
So then we went back to her house and I told her what shirts would go with which pants and shoes that she has, and took pictures of the outfits, which I'm going to e-mail to her and she can print out and put into a book, because she said she can never really figure out how to put outfits together.
All in all, I think it was successful, and she seemed happy with what she got and not too overwhelmed. So, now she has a few things to work with, and next time we go out, we'll look for some really dark trouser jeans (I'm still convincing her on this point), white pants, and also some jackets, because her office is always freezing, so she wears a grey hoodie to work over her clothes right now.
Any hourglass/pretty pears out there that might have some other suggestions for things to buy? I read over Angie's blog about the "pretty pear," but updated specific suggestions for things that have worked for you all would be fantastic.
Thank you!