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Hi! My first post here on head fi though I've been lurking for a bit. I've had my DT880/600 for about 4 years. Can't say how it compares to the 250/32 ohm versions so I'll refrain from commenting. It is one of my favorite headphones. Nowadays I find myself reaching for the HD600 more, I guess it's just a matter of changing tastes. The DT880, however, is my first love. It has weathered a lot of headphone purchases and I've never even thought of selling it to fund another purchase.
Which one do you think is the better overall headphone?
Which one you prefer will be totally up to you and what sound signature you prefer and what qualities in a headphone you consider most important. The HD600 has better, more forward mids while the DT880 has better, more detailed highs. Neither have a whole lot of bass but both have very high quality bass and both respond very well to a good bass-emphasized EQ. Lots of people love the quality of the DT880's bass but I slightly prefer the HD600's. Its bass can seemingly be EQ'd infinitely. I have one particular EQ setting with a
HUGE sub-bass emphasis and with it I get an amazing amount of high quality bass with no distortion, an amount of quality and punch that I previously thought impossible with open cans. On the other hand, with the DT880s, although also impressively versatile and also seemingly impervious to bass distortion, there seems to be a point at which further bass EQ has no effect. As such it can't quite reach the level of head-rumbling bass that the HD600 can produce. However, none of this crazy bass EQ'ing will be necessary for you if you don't listen to or enjoy very bassy genres and even without EQ they both do surprisingly well with bassy genres IMO.
Soundstage width is about even. Neither have extremely wide or deep soundstages but are still definitely better than closed cans in that regard. Because of the forward mids on the HD600 most people will perceive a slightly wider soundstage on the DT880s.
Both are extremely comfortable and breathable. Its hard to pick a winner in comfort. They are both loads more comfy than the huge majority of cans out there. Its not that all other cans are uncomfortable, these two are just extremely comfy and most people will be very happy with the comfort of either.
The DT880 isolates a bit better but neither are a good choice if you need good isolation since they are both open-backed.
Both are extremely good headphones. If you value detail retrieval highly get the DT880s. If you value mids and a warm sound that is not fatiguing get the HD600.
But all that said... after extensive use of both I have to tip my hat to the HD600. I consider it, overall, the technically superior headphone of the two.