Beg, borrow, or steal something from Capsule or one of the showrooms for him. More realistically, he may buy himself anything, but he probably doesn't have access to everything, nor is he likely to know every brand. Get him something that isn't available in NYC. For a guy who is probably "streetwear lite", maybe a Stars&Perfect Tens belt from Toronto (~$150), or something from Sydney's eponymous store. Or an Entermodal wallet from Portland. Gimme a call if you decide on this and want a hand.