I so feel everyone's pain. It is so hard to balance what to get kids to wear.
I did most of my son's early fall/ spring shopping in June. I got tons of outfits at The Children's Place for about $150. I also picked up a few things at Target.
He has to have a new backpack this year because his old one is too small, and I usually order that from Land's End: his last one lasted 4 years!!
I'll hit up Elder Beerman's, Kohl's, and JC Penney's for clearance and sale items over the next month or so for a few more hot weather outfits and some late fall/ winter clothes. He's outgrown all of his coats and shoes, so that is a big expense over the next few months.
He's in middle school this year and totally self-conscious about "fitting in"- not in the sense of doing what everyone else is doing (he definitely doesn't care about that), but he doesn't want to look like a "dork." So depending on how you look at it, my biggest "help" or problem is that his high school cousins and his cousin who is in his class are girls- and big time into fashion, so they have decided to help "dress" him this fall. They have taken him shopping and have had him model everything. They have also told him how to wear his clothes.
He totally loves it!! But he has fallen in love with Abercrombie (he loves the feel of their shirts- thanks, girls) and Zara, so we are "accessorizing" his wardrobe with those brands- without breaking my wallet.
Not fun to buy uniform clothes! Because I still have to buy 'everyday' clothes too, this isn't helping my budget any. 
