I could write a long paraghraph, but I will just say this: Focal Elex, Verum 1, Denon 5k (there’s also the ESP95X which I have yet to unpack so I can’t comment on it) don’t need a crazy amp and I will gladly match them up with the Timeless or similarly priced IEMs any time of day. Same for other headphones though, especially things like the 6XX, 560S which are pretty overrated imo.
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I think the background noise reduction provided by IEMs and the potential impact on dynamic range could be a factor in your (OP’s) perception.
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I’d agree, somewhat more forgiving headphones when it comes to amps, they don’t need one, but they sure benefit from having a nice one (also not to ignore the dac, since if the dac can’t do it properly, neither can the rest of the downstream components/chain)
The 560s wasn’t really as special as some made it out to be for me, although I think the 6 series senns can be incredible with the right pairing, but it’s a lot more picky amp wise than a lot of the aforementioned. But still I see many not really a fan of it, it’s a specific sound for a specific taste
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Open HP’s = a hot, sweaty and heavy way to fail at replicating speakers…Closed back HP’s = even hotter and heavier way to fail at replicating IEM’s…Simples.
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IEMs = a failure at both replicating speakers and headphones. I personally wouldn’t take an approach like this because I don’t really think headphone designers are really trying to replicate speakers or iems, or iems replicating headphones or speakers, and definitely not speakers trying to replicate headphones or iems lol. All 3 provide distinctly different experiences from each other, imo they figured out long ago that trying to replicate the experience of another format/medium wasn’t really that fruitful and it was better to focus on what the format they chose did best at. If you are going to go about making an iem, might as well focus on taking advantage of what in ears do best rather than trying to turn it into something it’s not, same goes with other formats. At least that’s just been my experience with the 3
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I liked that 
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Very wise thoughts. You should not try to do one thing with another!
Doesn’t help that I have an old 650 which probably sounds different than the 6XX… I accidentally wrote 6XX cause I’ve absorbed the notion that both should sound the same but they probably don’t…
They don’t sound exactly the same but they are close enough to where I think it’s safe to use them somewhat interchangeably, they are more similar than not
But this is what makes us human.
Many have asked what differentiates humans from other animals. Some point to a “soul” or “spirit”, but thus far, we have been unable to scientifically observe or measure this aspect, so I will dodge the metaphysical question as not able to be compared at this time.
However, others have tried to point to intelligence as the difference. This argument is continuing to decay and crumble as we learn how very intelligent many of our cousins in the animal kingdom actually are. Others try to use our language as a point of differentiation. However, again, the vocalizations of many of the great apes as well as those of marine mammals are more and more beginning to be revealed as extremely complex, communicating not just simple intents, but emotional and coordinative logistical information, and even regional dialects are being revealed. The more we learn, the more the language argument is crumbling as well. Finally, as a last ditch effort, some will point to tool use and/ or manufacture as being what makes us different. However, this argument too is beginning to crumble as we have observed some apes not only using sticks and rocks, but using sticks and rocks on one another to improve the intended function, and then keeping a well made tool for future use.
Only the human, however, can deliberately choose the wrong tool for the job.
Only a human would be laying under an American made car, with a set of imperial sized sockets and wrenches, and discover that the bolt he needs to remove is metric in size. Now, this human knows he has a set of metric wrenches 15’ away at his toolbox, but heck, it’s only one bolt, so he grabs the pliers that are right next to him and tries to use them to remove this bolt. Only a human will skin all four knuckles on his right hand when the pliers slip, because he was too lazy to climb out from under the car and walk the 15’ to get the correct tool.
Only a human can deliberately choose the wrong tool for the job. This is what makes us unique in the animal kingdom.
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Yes, only man makes the same mistake twice.
I might’ve made this specific mistake a few more than twice 
That’s right. In fact, the strange thing is that even very intelligent people make the same mistake two, three, four or more times. That’s how we differed from animals - they don’t!
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Any thoughts on the Edition X V2 vs other Hifimans like Arya/Ananda?
I will add that budget IEM’s likely sound better than budget headphones, but competition gets tougher as the budget goes up.
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My personal take is that (open back) headphones sound more natural and have a wider soundstage at every price point.
However, IEMs have better technicalities like resolution and instrument separation and general clarity especially in the lower and mid price points until about $1000 where you’ve got something like the Focal Clear.
And my controversial opinion is that IEMs are better than closed-back headphones at all price points.
So to summarize, my thoughts are you either want to spend a small fortune to get a really nice open-back headphone which will have the best timbre and excellent technicalities but will also be much more limited in its use cases or get some IEMs.
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An older thread, but much has changed, especially in the world of IEMs just in the last few years. I’d like to offer my 2 cents when it comes to the high end / TOTL market.
I think it definitely depends on what you prioritize and what your preferences are. I’ve learned through trial and error that I think high end IEMs are better than any headphone currently available. For headphones I own the Susvara, Elite, Empyrean II, Atrium, Clears, and HE1000 V2. For IEMs I’ve owned the U4S and U12T, and now the newer Grand Maestro. So all very high end comparisons.
With high end IEMs, the level of detail is unbeatable. The U12T makes the Susvara sound muddy in comparison, and the Susvara is known as one of the best for detail. For this reason alone I struggle to go back to headphones when there is just so much detail and clarity.
Bass quantity with “bass canon” IEMs is also just unbeatable compared to headphones. It’s so much bass quantity that it’s actually shocking when you first experience it. It took some time to get used to such a different tuning, but once you do it’s hard to go back. U12T and Grand Maestro makes open back headphones sound bass deficient in comparison.
IEMs can’t really compete on sound stage and openness, because physics, but they are getting better and better. It’s actually shocking how much sound stage you can get from the Grand Maestro. I wouldn’t say it’s as wide as most open backs but it’s really impressive for what it is. To the point where it’s not something I miss.
One complaint I have with IEMs is the way treble sounds. I don’t mean frequency response. But it sounds… how do I describe it… a tad tin-y? A little metallic? It doesn’t bother me most of the time but it does have me sometimes reaching for my Susvaras to see if maybe I’d prefer them but because of all the other qualities I like from my IEMs I always go back.
One other issue with IEMs is because they are so detailed and so close to your ear, they reveal any flaws in recordings like crazy. Even compared to the Susvaras or the sibilance revealing Elites I have never before been so turned off of certain recordings that have distortion or microphone peaking. IEMs really highlight it like nothing else.
So with all of that said, it all depends on your preferences. Do you want a flatter frequency response with wide soundstage and realistic trebles? Well you’ll probably prefer headphones. Do you want lots of bass, detail, clarity, punch, and fun? IEMs all the way then. Of course, there’s always going to be outliers to this. Not all IEMs are bass canons, and not all open back headphones have a big sound stage I.E. Atriums. And I’m really only comparing TOTL headphones to TOTL IEMs which is a different market. I’ve heard horrible IEMs at all price ranges and the same goes for headphones. And if you don’t get a perfect deal with IEMs you’ll never enjoy them no matter what. So your mileage may vary.
Lastly, when it comes to practicality, IEMs win hands down. Noise isolation, portability, low power requirements, being able to use them on the go or when exercising… no comparison.
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I enjoyed this read. I will have to take your word for it, for as curious as I am about them, I can’t wear IEMs because my ear canals are too messed up to support therm. I have been told by my surgeon not to do it, so that is that. That said, I have always thought that sticking those things in your ear canals would not be comfortable. My big brother is a bass player, and he can’t stand them. So I reckon I’ll be sticking to headphones! 
… not recommended by any doctor in the universe because they stick into your ear canal… no comparison. 
Also they can never do ‘real’ sub-bass that slams against your skin, because again physics.
Jeez, can’t say anything anymore without some smart alec coming around with comments like this. I tried to write something that might help someone with the sound differences between headphones and IEMs, not to discuss what doctors think about them or to debate what “real sub bass” is.
No offense to whoever you are, just tired of this pattern. I won’t be commenting again so if you just want to roast me knowing I won’t respond go ahead.