Take advantage of the personal shoppers at Nordstrom (make sure they know your budget) Many personal shoppers are a free service. If you go with a stylist (also very good), you do pay for most of these services but they are good at what they do and may not work specifically with 1 store.
I have a friend who works at White House Black Market and when they get something in that is "me" she holds my size (2) until I get in to try on because my size typically goes first. I have some great basic pieces from here and some fun pieces as well. She has chosen some things that I would never select from a clothing rack that are some of my favorite pieces. They do this for a lot of people at White House Black Market.
Ann Taylor and Ann Taylor Loft have employees with a good eye for what looks great on someone as well.
A lot of boutiques will have nice things as well.
I know being a teacher, it is easy to get in a rut with clothing plus you need durability and something that you can clean easily. I admit, my good clothes go to the cleaners and that can get pricey, especially for women's clothing.
Good luck