Clothing is quite a personal thing and everyone’s taste is different. How about offering to buy the cold weather stuff he wants when he gets there? That way he gets exactly what he wants and needs and you benefit from the fact it’s probably cheaper in Canada.
Find out the main outdoor clothing shops near where he will be living. Buy him a £100 gift voucher for that store. It may not have the personal touch but he will get something useful that he will use.
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