Hope you don't mind me putting my 2 cents in.
Bays can work on a guy - but it depends on the guy. There are two gents on the Mulberry forum who have bays - one has a ticking stripe bays and he looks absolutely fabulous, and the other I don't remember the colourway.
Both men a fashionistas oozing with confidence, they own it - so I guess it comes down to your BF and his style.
IWantANewBag suggestion of a messenger is a good one. My DH wears a messenger also and loves it (not Mulberry, another brand).