A tie. Heh.
You want something specifically male-oriented? Would something transman-related work? New binder, packy, something like that?
Leather Dopp kit, if he does any traveling at all--it's nice to have one, just in case, and it's very manly. You can even stock it up for him if you want to. Or he can take it to work or keep it in his trunk for emergencies.
Men's manicure set. They're different from women's.
A nice, full-sized, pushbutton black umbrella. Kind of a joke there--we always talk about the trans umbrella; now you can give him one. But by all rights a REAL trans umbrella should probably be multicolored, rainbow-colored.