Released in 2017, the Bose SoundWear Companion is a different kind of wireless headset. It doesn’t have any earcups or earbuds, but instead it sits around your neck adn has speakers that shoot sound up towards your ear — it’s essentially a portable speaker that sits around your neck. It’s water-resistant, so you can technically work out while wearing it, but it’s really designed for the person who works at home. It’s comfortable enough to wear for lengthy periods of time, but it also has excellent built-in microphones and works great as a speakerphone.
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.

In-ear headphones are like earbuds but are an upgrade to them. These headphones fit into the wearer's ear canal and stay in place with the use of foam or rubber tips. These tips are available in custom sizes so they can fit each individual wearer. When a proper fit's achieved, in-ear headphones reduce outside noise and deliver sound quality at about the same level as over-ear and on-ear headphones.
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