As someone who runs around in jeans and patagonia much of the time, maybe I'm not qualifieed, but ehre's my understanding.

You've got Classic and then you've got Seasonal Trends. Classic are things you can invest in and keep around for years; trends are good for a season or two before they look dated. Since I don't know what the heck I am doing for staying on top of things for when I do need to step it up, I am a big fan of going to better stores with good sales help. Macy's is my favorite. Those gals know how to help you find what you need, and make sure it looks good on you. Plus their sales can't be beat. Nordstrom's is another.