Ladies (sorry to be so presumptuous) but labelling is going to become your passion for however long your darling is at school. The only way to go is woven labels. Boarding school and sewing seems to go hand in hand.
DS has been boarding for the last 5 years first weekly at prep, now full at senior school and the thing I have learnt is label everything, I even do pencils. Superglue is my best friend for all non-clothing items.
Labelling is just one of those chores you have to do. The washing nets do work however after buying lots nice M&S and John Lewis undies at first, found lots of items were "borrowed" by other pupils (that may be a boy thing). It is now a job lot from Primark for socks and pants. Plain black and they are thrown away each academic year if they get to the end. I keep a bag of replacements already sewn and to reduce the chore, sew throughout the year and keep in a bag. As my DS is a full boarder he has some nice pants and socks for weekends but wears plain black boxer shorts during the week. For my DS's school, each child has a school number as well as name on their labels and they are quite strict on the placement of labels and that everything must labelled even socks. If you are wondering how to do socks, fold label in half with the number at the top, and sew horizontally across each sock. I don't sew but have purchased a sewing machine because although schools have a sewing service (they charge £1 per item at DS school), a sewing machine will payback within a year because of all the items they go through. Pants, I sew the labels on the cuff of the left leg, that way if borrowed, it is very visible who it belongs to.
Highly recommend a tuck box ideally with a re-enforced lid so they can sit on it. Had my DS box clad in metal and it is still going strong after 5 years.
If I can give one tip, it is send food parcels even if they are coming home at the weekend, with a funny note inside. Ds loves them. I fill it with things like noodles, crisps, sweets, cookies the odd cake but it is the joy he gets when a parcel arrives.
CathyandClaire, your child's tutor is going to be your number one contact. By the time the reports arrive, you don't want any surprises. At DS school, report cards approximately every 3 weeks and end of term reports twice yearly. Parents Meetings are once per year but given the scale just not an effective way to having a discussion.