a) cross body OR backpack
b) not too fashion-y (he's straight, so handbags are out of the question)
c) doesn't deviate too much from his personal style
However, while at the KnowShow, I saw some pretty amazing bags. One brand in particular, recommended to me by at least a couple male blogger friends, was there, and let's just say, it was love.
Best known for being a skate brand, Element showed some great pieces at the KnowShow, illustrating their evolution. The brand had some great men's bags at the KnowShow. These 2 were my favourite - I love the denim of the backpack and the collegiate feel of the duffle.
Penfield has been known for their outerwear - specifically their down-filled coats. Their products are made for the harsh demands of the New England climate and have been around since 1975. With nearly 40 years of industry experience, I would bet that Penfield's bags stand the test. Perfect for Vancouver's wet weather.
My personal preference (and also as recommended to me). Herschel Supply is...Surprise!...local! That's right folks, these fine bags and wallets are based out of Vancity. The aesthetic of the products is simple, yet detailed. By picking from a brand that specializes, the selection is much broader - there are varying patterns, colours, and styles - so your biggest problem would be deciding which bag to get.