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At first I wanted to carry IWB, but after some thought and research I like the idea of a Kydex holster worn OWB, comfort being the main issue.
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Neither method will be totally comfortable. Personally I prefer OWB myself but be prepared to try a couple methods before you settle on mode of carry. It's a highly personal and subjective thing.
Additionally, leather carries better and is more comfortable than kydex in my opinion so don't rule out a leather holster.
The hammer getting caught on your clothing is greatly exaggerated in my experience.