Communication headsets are used for two-way communication and typically consist of a headphone and attached microphone. Such headsets are used in a variety of professions as aviation, military, sports, music, and many service-oriented sectors. They come in all shapes and sizes, depending on use, required noise attenuation, and fidelity of communication needed.
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Ok, it’s been a month and a lot of new experience. I’ve auditoned ATH M-50 (clamp’s too tight; they sweat my ears just from few minutes of exposure) and Senn HD 600 (the velour pad is amazingly comfortable & size is ok). So, long story short, now I can refine my search to: circumaural&non-pleather/foam pads, which brought me to Senn HD 439 (cloth) & 518 (velour).
Supra-aural headphones or on-ear headphones have pads that press against the ears, rather than around them. They were commonly bundled with personal stereos during the 1980s. This type of headphone generally tends to be smaller and lighter than circumaural headphones, resulting in less attenuation of outside noise. Supra-aural headphones can also lead to discomfort due to the pressure on the ear as compared to circumaural headphones that sit around the ear. Comfort may vary due to the earcup material.
The FiiO E17 “Alpin” + AIAIAI TMA-1 or Pro700 Mk2 seem like a mix you’d recommend, but I’m concerned those cans will be uncomfortable for day-long use.  Also I don’t know if that DAC/amp is the best for my style of music/headphones.  Third, some of my techno tracks have stunning vocals, and I don’t want to miss out on those high notes while enjoying the bass.
Every single Bluetooth codec has significant quality issues—despite many creative solutions employed to make the most of the limited bandwidth the standards employ. For those keeping score at home: not a single codec available can meet wired signal quality. Though Bluetooth audio has come a long way since its noisy beginnings, it’s still not ready to replace the headphone jack. Qualcomm’s aptx HD, and Sony’s LDAC 990kbps codecs come close, but everything else falls far short of the mark.

Smaller earbud type earpieces, which plugged into the user's ear canal, were first developed for hearing aids. They became widely used with transistor radios, which commercially appeared in 1954 with the introduction of the Regency TR-1. The most popular audio device in history, the transistor radio changed listening habits, allowing people to listen to radio anywhere. The earbud uses either a moving iron driver or a piezoelectric crystal to produce sound. The 3.5 mm radio and phone connector, which is the most commonly used in portable application today, has been used at least since the Sony EFM-117J transistor radio, which was released in 1964.[9][10] Its popularity was reinforced with its use on the Walkman portable tape player in 1979.
A: Absolutely not... unless you're just looking for an excuse to try something new. But if you're not made of money, you can always hit up the manufacturer for a pair of replacement tips. Most earbuds only come with one set of each size, so losing one can be annoying. If you're in an experimental mood, Comply offers aftermarket tips that fit your brand and come in a variety of materials.

The rule that I use is that the bigger the size of the headphone, the bigger the need for amplification. Of course factors like driver sensitivity and impedance will matter, but the general rule of thumb is, use a dedicated headphone amplifier for a full size headphone. Even a portable amplifier can be enough, depending on the type of the headphones.
There are many good articles here on Headfonia. You could click on Buyers’ Guides and read through those, then click on the Headphones topic header for each individual report. The “process” you go through is learning your own sound preferences, then matching that to the products that are available. It is a process, so you have to learn the major differences. Any shortcuts you take might be OK, but when you buy something that you discover you don’t like, make sure you can return that item.
Whether you wear headphones for your daily commute, regular workouts, or just for jamming out at home, you need a good pair that’s comfortable and can make everything sound great. Headphone tech has evolved significantly, too, so some pairs can do a lot more than just play sound. It’s not tough to find a pair that can connect to your smartphone wirelessly, or one that can keep outside commotion out.
The Samsung Galaxy Buds are one of the best-scoring portable Bluetooth headphones Consumer Reports has ever tested. That’s all the more impressive given their “true wireless” design, meaning the model doesn’t have a cord connecting the left earbud to the right. That’s the same design scheme popularized by Apple’s AirPods, but our testers say the Galaxy Buds sound dramatically better.
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.
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.