i think it would!
i thought the smallest size id ever go was a work, but today i was in neiman while my sister went into vickys to play around with bra's, i was playing around with twiggys, and i actually really liked the way it looked with my outfit (the twiggy is REALLY long, so it reminded me of carrying a small duffle bag, especially with the shoulder strap!).
even though it's a womens bag, the less flaming a man dresses, the more he can pull of the smaller moto bags, IMO. id still count the box and first out of the question though!