Ontwo. That's what I used and my helmet even had them crammed up against my ears. If you don't mind constantly changing volume then they should work.

Inner pocket of my jacket or my tankbag when I use it

Yeah, I figure that might be a problem. We'll see

Also, I would put my helmet on first. Then slide the speakers up so they were nice and tight.

I won't even get into my idea of speakers.... :lol:

yeah we know, we make fun of your type. No one wants to hear your shitty grandpa music.

:lol:

Just for a different solution. One I've been putting off, but now kick myself for taking so long... custom ear plugs with speakers fitted inside. Had a mold made of my weird ears, chose the color clear for the plugs (would have to look to see them) and they arrived a week later.

Eureka! No more fiddling with getting plugs or ear phones/plugs to fit, with wind noise still somewhat present, having them come loose during a ride, or having them unseated when putting on the helmet. Plugs pop in an out, perfectly fitted to your ears. Can still hear voices and the sweet bike. Kinda pricey... $100 for plugs only, $200 for plugs with speakers (Outstanding... don't have to have the iPod/MP3 volume so high anymore to hear over the wind). Anyway, just something to consider as a longterm solution that will pay for itself many times over.

http://www.earinc.com/m-motorsports.php

Yeah, I've got a friend who has those. I just don't have the cash for that. If I did, I would spend it on tires