I think it’s fair to compare the Grados and HD598, but the M50 is very different and seems not to fit in that comparison. The DT770 is a better comparison to the M50, although the 770 is a better more expensive item. A long time ago I had a Grado 325 and a Sennheiser HD565 – very similar, very enjoyable. Today for that type of sound I might choose the Soundmagic HP100.
The Bose QuietComfort 25 were released in 2015 and you can still buy them today. They are kind of like a wired version of the Bose QuietComfort 35. They have a slightly dated look, and boast almost as good levels of active noise-cancellation and sound quality as Bose’s QuietComfort 35. The important thing to remember is that even though these are wired headphones, they still need to be charged so you can turn on the active noise cancellation. Otherwise, they just work as normal over-ear headphones.
For older models of telephones, the headset microphone impedance is different from that of the original handset, requiring a telephone amplifier for the telephone headset. A telephone amplifier provides basic pin-alignment similar to a telephone headset adaptor, but it also offers sound amplification for the microphone as well as the loudspeakers. Most models of telephone amplifiers offer volume control for loudspeaker as well as microphone, mute function and switching between headset and handset. Telephone amplifiers are powered by batteries or AC adaptors.
The iPhone will drive the headphone fine and make a very nice sound, but the amp will make a big improvement in harmonic extension and soundstage. Use the amp whenever possible. Both Headfonia and I concur that the E07k is a great amp, and probably the best thing you can get for up to twice the price. I’m familiar only with the E07k, the E17, and the E12. I think the E07k beats the E17 (and both are also USB DACs), while the E12 is just an amp, and has a darker sound but with more power for inefficient headphones. The Philips is not inefficient.
These early headphones used moving iron drivers,[7] with either single-ended or balanced armatures. The common single-ended type used voice coils wound around the poles of a permanent magnet, which were positioned close to a flexible steel diaphragm. The audio current through the coils varied the magnetic field of the magnet, exerting a varying force on the diaphragm, causing it to vibrate, creating sound waves. The requirement for high sensitivity meant that no damping was used, so the frequency response of the diaphragm had large peaks due to resonance, resulting in poor sound quality. These early models lacked padding, and were often uncomfortable to wear for long periods. Their impedance varied; headphones used in telegraph and telephone work had an impedance of 75 ohms. Those used with early wireless radio had more turns of finer wire to increase sensitivity. Impedance of 1000 to 2000 ohms was common, which suited both crystal sets and triode receivers. Some very sensitive headphones, such as those manufactured by Brandes around 1919, were commonly used for early radio work.

I think it’s fair to compare the Grados and HD598, but the M50 is very different and seems not to fit in that comparison. The DT770 is a better comparison to the M50, although the 770 is a better more expensive item. A long time ago I had a Grado 325 and a Sennheiser HD565 – very similar, very enjoyable. Today for that type of sound I might choose the Soundmagic HP100.
The DT770 is fine – not basshead, the COP is the same size and configuration as the 770, and both of those, large though they are, are “tighter” built so they feel less clunky than the M50. But the biggest problem for you is that the smaller headphones under $200 almost all have a steeply rolled-off treble, which is trouble for the more refined type of music. One possible exception is the Harman Soho.

Time to invest in a new set of headphones? It’s a hugely crowded market with hundreds of models to choose from, so here’s a handy timesaver: The Sony WH-1000xM3 are the best headphones. In fact, their combination of top-notch audio quality, superb noise cancellation, and dependable wireless performance is such a strong formula, we named the WH-1000xM3 the best wireless headphones and the best noise-canceling headphones, too.
Despite big promises from Bluetooth’s only Hi-res codec, the standard doesn’t really deliver at best, and it falls far short with its basic 330kbps setting. Both the 660kbps and 990kbps connections offer decent quality, but the 330kbps setting has a lot of noise—and a comparatively poor frequency response with higher-def content. You probably won’t hear it, but it definitely falls short of the marketing.

Headphones (or head-phones in the early days of telephony and radio) traditionally refer to a pair of small loudspeaker drivers worn on or around the head over a user's ears. They are electroacoustic transducers, which convert an electrical signal to a corresponding sound. Headphones let a single user listen to an audio source privately, in contrast to a loudspeaker, which emits sound into the open air for anyone nearby to hear. Headphones are also known as earspeakers, earphones[1] or, colloquially, cans.[2] Circumaural ('around the ear') and supra-aural ('over the ear') headphones use a band over the top of the head to hold the speakers in place. Another type, known as earbuds or earpieces[1] consist of individual units that plug into the user's ear canal. A third type are bone conduction headphones, which typically wrap around the back of the head and rest in front of the ear canal, leaving the ear canal open. In the context of telecommunication, a headset is a combination of headphone and microphone.

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