Music keeps me energized all day (and into the night) at work — 70% electronica/dance/DNB, 20% rock, 5% hip hip and 5% other/classical — but I’m tired of low-quality sound and I’m ready to put my money where my ears are.  I want to buy a USB DAC + Headphone amp, buy headphones (or, per your recommendation, to buy 2 pair) to complement the amp and my choice of music, and get great desktop sound for around $350.
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.
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.

If you’re buying wireless headphones, keep a spare pair of wired headphones around in case the others run out of battery. Wireless headphones are definitely the future, and the convenience is a huge benefit, but they rely on battery power to work their magic, and batteries run out. If you’re going to be in a place where you won’t be able to recharge your wireless headphones, consider keeping a backup wired pair with you so the music never has to stop.
That depends on what you’re using them for and how much you’re willing to spend. At the high-end, over-ear and in-ear headphones can both perform fantastically. For those of us not willing to spend thousands on headphones, over-ear headphones typically offer better bass response and a bigger soundstage, but in-ear headphones are significantly more portable and convenient — especially wireless earbuds.
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).

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Open back usually results in more natural sound, but they leak sound in and out. This means you probably can’t use them in a library or a plane flight since the sound of your music will leak out and disturb the people around you. You also can’t use them on loud public places since noise from the outside will disturb your music. Therefore, even though open back would give you more natural reproduction, for these reasons their use is limited to mostly at home or in the office (if you have your own space that is).

Telephone headsets connect to a fixed-line telephone system. A telephone headset functions by replacing the handset of a telephone. Headsets for standard corded telephones are fitted with a standard 4P4C commonly called an RJ-9 connector. Headsets are also available with 2.5 mm jack sockets for many DECT phones and other applications. Cordless bluetooth headsets are available, and often used with mobile telephones. Headsets are widely used for telephone-intensive jobs, in particular by call centre workers. They are also used by anyone wishing to hold telephone conversations with both hands free.
Open back usually results in more natural sound, but they leak sound in and out. This means you probably can’t use them in a library or a plane flight since the sound of your music will leak out and disturb the people around you. You also can’t use them on loud public places since noise from the outside will disturb your music. Therefore, even though open back would give you more natural reproduction, for these reasons their use is limited to mostly at home or in the office (if you have your own space that is).
Active noise-cancelling headphones use a microphone, amplifier, and speaker to pick up, amplify, and play ambient noise in phase-reversed form; this to some extent cancels out unwanted noise from the environment without affecting the desired sound source, which is not picked up and reversed by the microphone. They require a power source, usually a battery, to drive their circuitry. Active noise cancelling headphones can attenuate ambient noise by 20 dB or more, but the active circuitry is mainly effective on constant sounds and at lower frequencies, rather than sharp sounds and voices. Some noise cancelling headphones are designed mainly to reduce low-frequency engine and travel noise in aircraft, trains, and automobiles, and are less effective in environments with other types of noise.
Passive noise isolation is essentially using the body of the earphone, either over or in the ear, as a passive earplug that simply blocks out sound. The headphone types that provide most attenuation are in-ear canal headphones and closed-back headphones, both circumaural and supra aural. Open-back and earbud headphones provide some passive noise isolation, but much less than the others. Typical closed-back headphones block 8 to 12 dB, and in-ears anywhere from 10 to 15 dB. Some models have been specifically designed for drummers to facilitate the drummer monitoring the recorded sound while reducing sound directly from the drums as much as possible. Such headphones claim to reduce ambient noise by around 25 dB.
The outer shells of in-ear headphones are made up of a variety of materials, such as plastic, aluminum, ceramic and other metal alloys. Because in-ear headphones engage the ear canal, they can be prone to sliding out, and they block out much environmental noise. Lack of sound from the environment can be a problem when sound is a necessary cue for safety or other reasons, as when walking, driving, or riding near or in vehicular traffic.[19]
The problem is made even worse by the fact that Android phones can’t handle AAC in a method that approaches Apple’s performance with the codec. Consequently, we will no longer be recommending AAC-only headsets here at SoundGuys, as the experience is that broken from source to source. The results are crappier and noisier than the other codecs by a longshot.
The E25BT didn’t score quite as high for audio quality as other models on this list, and it lacks some features you’ll find on certain other models, such as water resistance and extended battery life. But if you want a pair of wireless headphones that provide decent sound at a fraction of the cost of its competitors, the E25BT is an appealing option.
Hearing risk from headphones' use also applies to workers who must wear electronic or communication headsets as part of their daily job (i.e., pilots, call center and dispatch operators, sound engineers, firefighters, etc.) and hearing damage depends on the exposure time. The National Institute for Occupational Safety and Health (NIOSH) recommends sound exposure not exceed 85 dB(A) over 8 hour work day as a time-weighted average.[35] NIOSH uses the 3-dB exchange rate often referred to as "time-intensity tradeoff" which means if sound exposure level is increased by 3 decibels, the duration of exposure should be cut in half. NIOSH published several documents targeted at protecting the hearing of workers who must wear communication headsets such as call center operators,[36] firefighters,[37] and musicians and sound engineers.[38]

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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