So I spend significantly more time outdoors than the average person, I bike a lot (about 10,000 miles / year) and so waterproofing is something I typically am concerned with, more so in winter we are approaching.
I make extensive use of waterproof bags, I usually have 2 or 3 of different sizes for different types of kit, a particularly thicker plastic material for my gadget stuff as gadgets have rougher sharper materials, and thinner bags for clothes.
I make extensive use of Android Wear which is a water resistant watch to be able to see and control a lot of the tasks which would cause a phone to be got out and used in the rain. I have also Anker Soundcore IE20 which are water resistant I keep around my neck (the magnets are cool!), so combined with the watch means I can see hear and control common tasks in the rain. This is ergonomically also the best as hands are free for the most part.
I'm usually with at a minimum the Powercore Slim (5000mah) to be able to charge the phone in a bag right up against the phone, and for longer trips also the Powercore 10000 which has excellent density of power (computing the volume and weight and dividing into mah to get the highest mah/oz and mah/cu.in) these are in the waterproof gadget bag with the phone.
I have a water resistant BT speaker for in the shower. I can't imagine a situation I'd want a waterproof speaker for outdoors as headphones suit my needs better.