"The picture's a little blurry, Mom, but that's ok. It'll hide your wrinkles." ~16-year-old
Andi recently asked me about how we tackle the seasonal clothing swap. In our part of California, autumn lasts approximately 24 hours and then BAM! It's winter. And cold. There's no real transitional time, and so our swap tends to be relatively quick and dirty, although I have gotten it down to a system that works for us.
First of all, I try to handle any new clothing that comes in by way of purchase or hand-me-downs right away. If I don't put it away, it languishes on a countertop somewhere, and typically all the way until the next season. I have big Rubbermaid boxes labeled by size and stored in a large hall closet. When we had a much smaller home, everything was in labeled boxes and kept in the garage.
Next, I keep an inventory of clothing we own, marked by sex and size. I make notes as necessary, noting whether a sweater is part of an outfit, etc. With a good inventory, I can be sure I'm not purchasing something we don't need or I can snatch up a really great sales rack deal even if no one is currently wearing that size. If it's on my inventory as a need, I tend to buy it.
When it comes time to actually try on clothes or swap them out, I find that taking one child at a time works best. I used to try to do the whole thing in a day or two, but I've found it stresses me out far less if I focus on one child per day. It then takes a week or more, but that's ok. No one will freeze or overheat in the meantime.
During our swap days, I keep donation bags at the ready. Right now we're handing clothes down to three different families, so I have their bags plus a thrift store bag labeled and handy. As I am doing laundry this week, I can grab clothes that need to go and just toss them into the appropriate bag.
Nothing is perfect. We find strays throughout the season, but I just pile them neatly on a shelf in the hall closet and deal with them when I can.