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My main hindrance with OWB isn't concealment. It's that I lose the use of my right front pocket. It's blocked by my OWB holster.

When I carry IWB, I have all pockets available. When carrying OWB, I'm down one pocket. That drives me nuts.

I carried OWB for the first time recently too. I just wore a long, untucked shirt (not the hawaiin style or anything like that though... almost more like a sweatshirt, but not thick).

I loved it, but felt so obvious at first. I went to Academy and felt like I was wearing a sign "I AM ARMED". No one noticed of course though.
And, I noticed how often I reach up for things on high shelves or above with my right hand. I had to keep switching to reaching with my left!