Boob mashing?

I'm one of those women you're talking about. :-) Most days I wear my small custom classic, stuffed full of books and school stuff. I wear it two ways. One is traditional messenger style, as in the video. I will admit that I don't tend to cinch it up as tight, because it was digging into my under arm area a bit when I did that, but I do wear the strap high up.

The other way I wear it -- more often -- is to slide the padded strap of my left-handed bag off my shoulder so that it's pressing sideways, not down. The strap ends up looking more level with the floor. I have a shoulder/neck injury, so what this wearing method does for me is makes most of the force going sideways compressing my upper bicep area (or whatever you call that) instead of the force going down, pressing my shoulder and neck. I have a lot of padding on my arms, so it's very comfortable. It also doesn't compress my chest at all, because the strap is going across my upper chest, far away from the sensitive parts.

I don't wear my bag for cycling, I wear it for a long public transit commute with a lot of walking. My sideways method does *not* work for cycling, as it allows for more movement than that, and the cross strap won't work when I'm wearing it that way.