Oh yeah!!! I totally hear you on the school stuff!
I "showed (relatively) poor" at school, as well as generally out of it socially, and I hated it. Interestingly, I always desperately wanted new school supplies -it was the first thing I shoplifted- and to this day, office supply stuff is still among my favourite. And I let myself get new scissors, paper, binders, etc, now :)
At the elementary school I went to, kids were kind to me -we were such a diverse group in every way, and there were kids much poorer and in rougher shape than me. (I was clean and groomed and healthy-looking, just not hip or stylish or anything and I lacked the special supplies.) But high school, no, I really got it there, because kids honed in on clothing brands, styles, hair, make-up, etc. That's where I started to understand that we had way less money -as well as some other things- than a lot of families did. (But again, we also had more than some families did.) I remember the moment, hearing people talk about what they got for Christmas. I was stunned. But the fact is, we got stuff for Christmas. Enough. And hand-selected for each of us. If we don't compare, we have a good chance of feeling really satisfied and happy.
Anyway, as a result, yep, my kid got brand new school supplies to start his new school-life. For me, my kid's development and psychology is considered very much in our Mustachianism. With his disabilities, he has enough social barriers to deal with without me imposing strong cost-saving measures into his social life. All his clothes are all from the thrift, but I make sure they're in excellent shape and look great on him as well as being comfortable for him in every way, and combining well with the rest of his stuff into cute outfits. I put a few conventional food items into his lunch every week, because it's important to him that he be eating the same as other kids (and then he's otherwise totally fine with the weird stuff I generally pack). I get those from the 50% aisle, but that doesn't show on the package. He spends his allowance on their expensive hot lunch program a couple of times a month. I pay the extra fees for field trips, etc. I know how cruel the school culture can be for a kid who shows poor.
Happily, the food bank fundraiser at school doesn't connect to specific families. They collect, then deliver it to food banks and the local hamper program that started this whole thread. So, no worries there.
I have tricks to make up for the costs of the above. His autism program got him an iPad, and rather than present it weeks ago when it came, I'll be putting it under the tree at Christmas. That way, his disability needs are met, and he has a Christmas like he's never had, but we still have money to help him survive "school culture". Another thing I did was, right from the start, spend nothing on extraneous baby gear, disposable diapers, formula, cute clothes, or even presents -because how much does a baby or toddler know about Christmas and presents anyway? Their whole life is a Christmas present! Anyway, all that time I was aware I was saving up for when clothes and hair, etc, would make a difference to his social life. We've just edged into that recently.
He *is* bummed that his newest ice skates are, like all the previous ones, used. But I do draw a line at points like those. It's one thing to spend $2 more on second-hand pants that look nicer than another, but no way am I spending $60-$160 on one season's ice skates. He's allowed to save his allowance if he wants stuff like that. So, I think he's getting sufficient "cultural safety" while he also learns about finances.