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While the Bose SoundSport In-Ear may not be the best sounding in-ear headphone for the money, the design and comfort level are great, and it's ideal for people who want this sort of headphone style without the need to jam the tips into their ear canals.
The Bose SoundLink Bluetooth On-Ear is pricey, but it's also one of the best -- if not the best -- on-ear wireless headphones to date.
The Bose SoundTrue On-Ear is a very comfortable everyday-use headphone that sounds good and collapses into a very compact carrying case.
The SoundLink Around-Ear Wireless Headphone II mixes a strong blend of comfort and performance in attractively designed wireless headphone.
If you're looking for comfortable in-ear headphones with very plump bass, the Klipsch R6i model will do it, but they're also short on detail and clarity.
Despite a couple of small flaws, the Monster iSport Victory offers a great fit, is water-resistant, and one of the better sounding in-ear sports headphones out there.
The Audiophiliac finds a lot to like about the Klipsch Reference On-Ear headphones.
The JLab Epics may look a little cheap, but they offer a comfortable, secure fit, and sound richer than their design would indicate.
If you're looking for a $150-$250 on-ear headphone, the well-built V-Moda XS should be on your short list.