I like the James Bond approach to riding in the rain. In one of the old movies, James Bond infiltrates some sort of fancy party, coming in under water. He climbs out of the water, pulls off the air tanks and dry suit, and there he is in a tuxedo.
I try to get the right gear so I can ride in regular clothes, covered by rain gear, arrive at work or home, take off the rain gear, and there I am comfortable and dry. So I look at rain days as chances to test the equipment.
It's a work in progress.