There is no amp in the world that is going to make the HD280 sound good. They are awful headphones. I've built better ones out of coathanders and sellotape.
Spend the money on a better pair. Some nice Ergo 2s for example. Easy to drive and don't sound like mud filtered through sand.
I haven't heard the HD555, but as far as both musical fun and comfort are concerned, there's no question i my mind that the Triport (AE) is the better headphone.
It looks prettier too, which is always nice.