This has forced me to de-lurk. I thoroughly understand, especially the part about being short. I'm 5 feet even, which means the only stores in the college town where I usually live that carry clothes that even come close to fitting are the department stores. And their petite selections are--no exaggeration--clothes my grandmother wore. Mint-green elastic-waist polyester blend pants with matching floral tops. I am only 32, for heaven's sake.
It's sad to put something on, think, "I look good," and then realize later that I look good for 1998.
I'm going on the job market this year, so during a trip to visit my family, I plan to clear out the Ann Taylor Loft--which is the only place I can find suits that fit and aren't old-ladyish or too businessy. But more expensive than my tall friends get to find at all the great sales for people with long legs. Grrrrr.
We're going shopping.
Do you have H&M? Assuming it doesn't only have the trashy-teenage section ("Young Attitude", I think), the women's section often has some really nice professional clothes. And cheap! And hip!
Ooh. Can I fly in and take you shopping?
I highly recommend Ann Taylor. Pretty good for us shorties. Expensive, but also pretty classic stuff (but not preppy) that holds up well, and not too old.
I, too, am short, and also recommend Ann Taylor. Also, I LOVE summer clothes and LOATHE winter. My recommendation for summery, but professional, is a camisole or other short or no-sleeve shirt underneath a seersucker, linen, or cotton jacket. Short or 3/4 length sleeves on the jacket are fine.
I've actually had pretty good luck with some of the newer women's clothes from L.L. Bean (for the professional alert level yellow) -- some nice knit 3/4 length sleeve tunics with V-necks that look a bit fancier than standard V-necks, and skirts and slacks that coordinate with them.
I confess, though, that I manage to get away with colored jeans and button-down shirts on teaching days. (On non-teaching days, I often have little enough human contact that I can get away with smart-alecky T-shirts.)
I obviously am not ready for administrative duties!
I actually like Eddie Bauer, but I'm average height, so I don't know how it works for shorter folks. In fact, I just came back from a shopping trip to the outlet mall, where I bought two shirts and one sweater from E.B. at a discount price, so I'm feeling newly pleased with the store.
I completely sympathize with feeling sartorially middle-aged. The reason that I went shopping today is because I couldn't find anything to wear to a dressy evening function a week ago and in the combing through my wardrobe I realized just how blah it all was.
I get things at Talbot's and Coldwater Creek these days. They make things that look good on middle-aged professional women with real figures. I like things that are structured but not uncomfortably so, and which don't require dry cleaning. I look for things made in the USA, but I'm not always successful.
I'm not in the US, so I can't recommend particular stores, but I would suggest - as a good academic - doing some research first to develop an overall aesthetic before you start shopping. This way the clothes you buy will all match, and you'll get more outfits from a limited number of purchases. Although there are a lot of horrible fashion magazines out there, finding a few in a style you like can help give you a sense of what's currently in stores, and suggest new looks you may not have thought of.
I often buy what would have been expensive clothes new from Ebay, too, which has saved me an absolute fortune.
I so sympathize with this post - the same thing drives me nuts. I want to wear Ann Taylor (or Ann Taylor Loft) clothes, but they're not quite cut for my current shape (the jackets work but not the pants). Talbots stuff is cut right for me, but a lot of it is a little too staid/formal for my taste. (I have a middle aged shape longing for younger people's clothes!) Plus the other thing with Talbots is so much of it is suits, which I don't really wear. I feel lost in between what I'd like to wear and what fits me.
Oh, and while I'm 5' 6" (not super tall, but not short), it doesn't help, because designers seem to assume that the only people with waists/hips my size are 6 feet tall. So lots of stuff is too long on me, too. Plus, I'm an A-cup, but I have broad shoulders, so I can end up in the weird situation of having tops that hang in front but pull across the shoulders. I just want my own personal tailor!
J.Jill petites on sale. Not the swoopy stuff, but the tailored trousers, skirts, and jackets.
I can so identify with this post. Trust me, it doesn't get that much easier if you are tall. I'm 5'11", and that just presents a whole different set of problems. I mostly go with Eddie Bauer to get the length I need. I also have a closet full of jackets that I'm afraid are looking out of style, but I don't really understand what is in style these days. . .
I think we all need to go shopping with profgrrrl 
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