Im a guy and I would not carry a Speedy 30, I think the size is too small for a guy But a Speedy 40 is perfect. I think larger womens bags suit men. Snoop was not well dressed at all in that photo and if you are using it for work and are smartly dressed, I think it would look good on you. Please buy what YOU want because at the end of the day, its you who is using the bag.