[FinancialWar]

seem like a stupid question but, I don't the correct convention on wear my headphone with hoodie, does it go on the outside of the hoodie cap because the cap won't fit over the headphone, or no hoodie cap when headphone is on.

 

[Bee inthe Attic]

I can't seem to find my official headphone rule-book, so I'll have to wing this one:
 
If you put the headphones on top of the hood, the sound will be muffled >> so bad option.
If you can't fit the hood over your headphones >> get a bigger hood, or use IEM's / smaller portable cans.
 
Third option >> move to a warmer climate where you don't need to wear a hood.
Fourth option >> wear the hood, ditch the headphones, and sing quietly to yourself to get your music fix.
 
Hope it all works out.