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I have strong ankles so I only wear boots during activities that require my ankle to be protected from getting hurt like chainsaw work, prescribed burning/wildland firefighting, using sharp tools, etc. The other exception that I make is for winter or if it is colder than 32F(0C).
Other than that though, I wear pic related for all my trail running and hiking/backpacking. I am with all the others who have stated the benefits of the breathable mesh. These shoes dry faster than a waterlogged boot. I also hate how heavy boots are.