OP should be prepared for the worst and should be packing his designer suitcase right now.
First time in prison what you can take (SA could be different of course)
Prisons have different rules on what you can have, what can get sent in, and so on. Expect to be annoyed.
Im a list person so I thought Id help OP out here.
Wear a cheap watch to court (hell obviously have to run out and buy one of those)
All toiletries (but dont assume you can keep all of them)
7 or 8 sets of underwear (undies and socks)
4 tops (t-shirt, polo top, long sleeved)
4 bottoms (tracksuit pants, trousers, jeans, shorts)
2 windcheaters or tracksuit tops or jumpers or jackets (no hoods)
1 pair of pyjamas
1 pair of shoes/runners (no doubt he has plenty of those courtesy of Nike)
1 pair of scuffs/slides/thongs
1 belt (small buckle)
1 cap
1 pair of reading glasses in soft case
6 books, 6 magazines and 6 photos
Stamps, writing paper and envelopes. (Im not so sure about this. He wont have the eloquent words to write)
Pens and pencils. (have a variety as not all are allowed)
A radio/alarm clock.
Cash (not too much as there are monthly limits)
Of course he'll need super soft toilet paper and especially scented soaps and fragrances. No doubt the family will be able to bring him a TV, iPad, mobile and all the other little niceties from home that a special person needs to make life bearable. Oh, and that coffee machine. Ah, a home away from home, sort of.