Dress: I have always found how to dress puzzling. I study it and copy as best I can, but I still fail frequently. Thank goodness for tenure, as jeans seems to pass for almost anything now. For my kids I have spent as much as a week of drop offs studying boy's pants, for instance, to figure out what kind of pants to buy DS (note, not jeans).
Ok this probably doesn't fit your budget. BUT....anything you buy at Hanna Andersson should get the job done. My own kids (admittedly they share clothes as they are the same gender) both packed their suitcases and commented how their pants from target each have a hole in the knee (all 3 pair) and yet the ones they've been wearing forever (or maybe 14 months?) from Hanna look brand new. It does kill me to buy a pair of pants that's almost as much as I spend on myself. But I can easily order their fall clothes in one setting. Better yet: when we got to cleveland and drive past Michigan City we stop at the outlet mall. Originally just to run off some steam and now to stock up on Hanna leggings. Worth the hour spent there. easily.