So, with that in mind, this is what I do. What I need is my storage container, black marker, pen and paper, and a few heavy coated paper department store bags.
First, I keep a plastic tote in a handy location like a closet or basement that is labeled with the child's name.
I don't let myself get overwhelmed. This project will actually be doing two for the time of one. It will restock their drawers with summer clothes and weed out small, outgrown or totally destroyed cold weather clothes making it easier to plan for the winter months.
Start with underwear and socks. Toss out what can't be used, even as play clothes. Start a list on the paper of items needed (ex. Johnny will need 2 new packages of underwear soon)
Go through subsequent drawers, noting which clothing items will need to be replaced. Keep a pile of bigger clothes for storage for the following fall, a trash pile, and a pile for fellow-moms-in-need/donations. Incidentally, I LOVE getting hand me downs and so do the kids, so pass on the kindness Once all the drawers are emptied and the list is written open the tote that has last year's summer clothes. I try to guesstimate what will fit but sometimes the kids go on a major growth spurt. Still, it's easier and cheaper than re-buying entire wardrobes from season to season. Do the same organizing with the tote clothes; one pile for wear now and one for too small/just won't fit.
Neatly exchange the summer clothes to the drawers, notating which clothes are still needed (Johnny could use a spare pair of swim trunks). Put the winter clothes in the tote and the pile of unwanted clothes in the bags for donation. The clothes that are trashed can be used as cleaning rags or see if the hubby needs them in the garage for washing the car (cotton shirts are great for this) or whatever it is they do with the cast-offs.
For the spring switch I see which high water pants that still fit in the waist can be made into cut-off shorts. If you sew, a quick hem is all that's needed. Ta-da! Instant short supply!
Now, take the list you've made and find one of those old-fashioned paper things called a calendar and stick it in under the month of August or whenever you start shopping for school clothes. Or, you could put the list closer to Christmas. Either way, you won't forget what you'll need to buy, the clothes will be in one place and ready to thin out and transfer.
If you're ambitious enough and have a good idea what size your child will be in when the weather cools off, go shopping. Yeah, permission to shop! All winter stuff is on clearance and marked down to move. Stock up on what you need guilt free and hold your chin up high when you brag how much you've saved.