Heres two of jorads (great work)
What I'm thinking is you cut longer than you need, measure and cut how long you need by wrapping around, then punch holes (leather hole puncher???). I am wondering if you overlap it slightly to make sure no gaps where the wood is visible. This is what I am worried about. Do you fold over the leather where it is weaved together with the strip so you can't see the edge that was cut? I basically have never done this, can ya tell?