My Sennheiser HD280 Pro cans, about 15 years old by now, are about as flat and 2-3 hours wearable at a time as I could ever need and/or afford. Something amazing about learning how things "should" sound in a reference mode, and then go take it to other systems to try it out...burn CD, play in car, laptop speakers, earbuds from SoundCloud on an iPhone...
For me, the joy of the H280 is that a: it leaks little sound in or out, and b: they can be played REALLY REALLY LOUD. Handy for putting on the drummer who needs to hear the acoustic guitar when tracking.
But flat? Ugh. Try a set of AKG K240 headphones! They're cheaper, much more neutral, and much more comfortable. They also leak sound into your surroundings pretty freely, so everyone else can enjoy your tunes, too...
Beyerdynamic dt770 pros. They won't break your bank and have good isolation. They're decently detailed, comfortable to wear, and pleasant to listen to hours on end. Not neutral, though. Good for bassheads.
Also, you can just buy Sennheiser 600s or 650s with a good reasonably priced DAC/amp and you will get a very good value and can probably just stop there. Satisficing this way is probably the best thing in the larger scheme. Being a can-head is an endless and expensive hobby.
I had those. Gave them to my girlfriend's brother. Didn't like the highs and made my ears sweaty. But I know lots of people who like the sound and the isolation. I suspect that individual differences make a huge difference, and the industry just doesn't have the technology to cheaply compensate for those (yet).
15 years is a lot. I own some HD380 Pro (reasonably flat for something closed, and supposedly a huge improvement over the HD280 which I haven't tested) and HD600 (flat as an ironing board), both purchased recently.
I'm curious... how well have your HD280 Pro endured through these 15 years?
Fantastic, I think they've "broken in" and given me that impression of not really coloring the sound a lot. I've sweat through 2 sets of ear cushions and the headband. I've bought a replacement headband but just left it off. They've been so trusty I consider them my go-to even though I don't really get the chance to formally sit down in the old ways anymore (more on the go sketches).
I second the 380s. They're pretty great, though they can get more fatiguing than I'd like after a few hours of listening due to the horizontal snugness. 7 5/8 hat size, YMMV. I use them every day despite that.
>they can get more fatiguing than I'd like after a few hours of listening due to the horizontal snugness
They get quite loose over time. I've had mine for a while, and I can barely feel I'm wearing them.