An interesting point. As you probably know the subjunctive form (mood) in English is not a very common form mainly because the construction of it is very similar to that of the indicative mood or non-subjunctive. You might be interested to read a piece I’ve written on it for the site. You’ll find this under the heading esl lessons and if you look in the index, you’ll come across the title Subjunctive. But to come back to the question you ask - I would choose option B, which in effect means that he should wear. You have suggested that he wear, which is also acceptable. The difference in form between wore and wear is that the first is past subjunctive and the second is present subjunctive. The difference in meaning is that the past is a little more remote and indirect and the present is more immediate and direct.