I live in a city where I can take the subway everywhere I need to go so I would prefer something over the shoulder rather than handheld like the leather briefcase I have now.

The problem with the briefcase is that there's no shoulder strap and I don't like not being able to free up both hands when I'm walking around or on the train. I just feel a bit odd standing around with this heavy bag in my hand.

There are a lot of cheap leather tote bags online that I feel would keep my laptop sufficiently protected but so many of the styles are labeled women's, even though to me they appear to be pretty unisex styles. Although "men's bags" as a category in stores feels rather new to me anyways.

Has anyone here bought a "ladies" bag online? What are your "rules" for picking a sufficiently "unisex" style? I dress like your average gay dude that lives in Boston, so I want sleek and simple styles.