I don't care what people think, but a guy walking into a room with a strap over their shoulder is going to draw some attention (Starbucks doesn't count).
BUT, this not just about an image issue. It is more about comfort COMBINED with image. This is not just about what men look like carrying purses in to places like Lowes or theaters. Women have it a little easier because they can throw their iPad in their purse, my wife does. Guys have to be a lot more selective, IMHO. And it isn't just what I think. It is what my wife thinks. She doesn't like me to look too OFF. 20+ years, she is used to me carrying something, cameras, Newton, now iPad, etc., but it still maters.
We don't all live in progressive cities. If I go to Houston for the day, I feel a lot less noticeable with a bag over my shoulder. But in my small city, it is a lot more obvious when I walk into a restaurant with a nurse. It doesnt help that I have pretty serious case of vitiligo, so people are going to look no matter what.
Anyway, point is, a lot of this depends on where you live. It is not likely for you to understand if you are in a big metroplex area like Houston, Seattle, San Fran, Austin, etc. Go shopping in the city of Beaumont to change your perspective.
No thanks, I grew up in Oklahoma City. I left for a reason.