I'd avoid anything that looked to SWATish, or military, unless you're in a combat zone. It for year round, not just Halloween, so I think he should stick with the leather one, that looks big city all the time. It's more serious, not costume. Just like I'll stick with the Timbuk2 stuff, it's designed for exactly what I use it for, so it not only makes sense, it looks sensible, serious even when I'm riding.