Basic questions for newbie

I mainly stream Qobuz into pi2aes/Roon to a Schitt Dac/vtl integrated amp. But I listen late at night after wife has gone to bed, keeps her awake. Vtl has a headphone out but is about 10’ from where I sit (Long cable, heavy?). 

I have no experience in headphones. What are options I should pay attention to? Do I just plug headphone in amp? Or run from my surface or iPhone ?  Or ???
Thx