Hi noddy
My nearly 13 year old seems to want new things all the time, so he is used to me saying no, or striking a deal with him.
As he likes clothes I have to be clear with him what clothes I buy him and how much I am prepared to spend.
I buy what I call the basics ie one new outfit approx four times a year, plus one coat, 2 or 3 new pairs of shoes depending on how his feet have grown and some extra t shirts etc.
The rest of his wardrobe comes from his christmas and birthday money or extra money he gets given. If he lost a basic bit of kit, ie his winter jacket, and the incident was a one-off, he would get a replacement from me as soon as I could afford it. But if it happenend again it would come out if his present money. And the replacement jacket would be a no frills one - something pretty functional.
I give him a set budget for basic clothing ie £30 for a new pair of school shoes. He begged for Kickers costing £65.00, so I gave him £30.00 towards them and he paid the rest out of his christmas present money.
If he someone stole hiss phone (a birthday present) again I would probably buy him a new one eventually, but if he lost it through sheer carelessness, I would make it part of his next birthday present, and only buy him a smaller, token present for his birthday. Or make him go without some promised treat/ present to pay for it.
We do deals like this months in advance of the dates. By september, ds had already organised his main christmas presents from us. I try to be very clear what money I will give him towards things. I am always glad when ds gets money from friends and relatives as it is very useful for topping up.
In your situation, how about telling your son that you will get him a skateboard for his birthday (or as an easter present, if you as a family give easter presents) but for now, his current skateboard fund will be paying for his replacement clothes.