I was looking around for a bluetooth speaker for my board when I came accross these sunglasses made by bose. They have speakers and gps build in and have an open design so I can hear things around me well. These seem perfect for esk8 because of them being lightweight and not annpying for people around me. When going to new places the maps capabilities of these would be amazing because from reviews they can tell you when to turn. I could have completely missed something but the only things I see wrong with them is the small battery (3-4 hrs on full charge) and riding at night. The night part can be easily avoided by just not wearing them which is a good idea anyway because one needs to be extra alert at night. https://www.google.com/amp/s/www.techhive.com/article/3337530/headphones/bose-frames-review.amp.html
I assume you’ll be wearing you helmet with these?
Full face like must guys use could be a bit tricky
Why not use airpods? 
These theoreticaly have better awareness because there is nothing in your ear and I have an android.
The boombotix pro is lightweight, durable, waterproof speaker that cips on to belts and has internal storage so you can ride without using your bluetooth
I’m sorry but to pipe music into your ears while riding a plank of wood at 30mph on the street is tantamount to suicide. Great for the off road boys though. Never in the city though please.
Even for off-road, nothing better than hearing the gravel slipping under your wheels 
But honestly earphones take away a lot of attention to the things happening around you.
Definitely don’t wear them while riding on the road.
You could try those bone conduction aftershokz headphones as they sit next to your ears but the awareness concern is still there ofcourse. you can hear your surroundings but it could very well remove your attention from your surroundings just like any other earphones
Because it’s apple
Did you try wearing a BT headphone around your neck (so not over your ears)?
Not perfect but that’s what I use for now : I still hear perfectly my surroundings & watch out for dogs, cars and trucks + I can enjoy music at low cruise speed (say till 15mph approx). It is very directional spread toward myself so I don’t bother people either.
At higher speed road and wind noise take over though. But it allows to focus more so is it a bad thing?
I’d call it the “Burnout Revenge” effect, if you’ve played the game you’ll understand haha
Edit : I use Sennheiser BT 4.50 for mobile rig, pretty good for a BT model with lot of punch.
i’ve always had portable BT speakers that hang off my backpack strap just under my shoulders/chest area.
You can still hear everything around you, and the speaker isnt too loud as its fairly near your head area