So this is the way I did it when I had 3 children in school. At one point I had one in high school, one in middle school, and one in elementary.
I would buy my youngest child's school clothes in May - minimum of 5 pairs of pants, 5 shirts, underwear and socks. I would put them in a plastic storage container with the child's name on it. The storage container usually cost about $4.
I would usually buy my daughter's clothes in June - the same and any dresses that she may want. Also, since she was in dance,pep squad and band, I would have to buy her uniforms the in July during the prep days. Once again all stored until school began in August.
Finally, I would buy my oldest son's clothes in July, not only because he was easy to shop for, but in addition to his clothes, I had to buy his soccer uniforms.
I generally buy the shoes in August since I could never seem to keep them out of them. Also, the major expense for August is school supplies. The elementary schools are easy since most of them supply the list, but middle schools and high schools are more difficult since they don't tell the students what they need until school begins.
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