Wired vs. wireless
Even in 2018, I'm not going to make a case for why you should switch to wireless headphones. Do I prefer Bluetooth sets over the tethered options? Definitely. However, I appreciate that wired headphones still have some utility -- namely, at-home listening with an amp. If that's you, you're probably going to want some audiophile-grade gear from the likes of Grado, Audeze, Sennheiser, AKG or others. For the purposes of this guide, though, I'm going to stick to the models that will likely appeal to a wider audience. And that's predominantly wireless headphones.
Like shoes, sunglasses and other items, there are different wear styles of headphones -- each lending different factors to the equation. And, just as with clothing and fashion accessories, you're probably going to have a preference for one over the others. Wireless and true wireless options abound for fans of earbuds. Over-ear and on-ear models are the more traditional headband construction, either with pads that sit on top of your ear or with larger ear cups that encircle your ear entirely.
Generally speaking, earbuds are the more affordable option, with on-ear coming next and over-ear models typically ranking as the most expensive. Of course, this isn't a hard-and-fast rule: You can find earbuds that cost $300 or more, and there are over-ear models that are cheaper than popular on-ear sets. Still, when considering cost and wear style, that general rule of thumb will give you an idea of how much you should be ready to spend. Take Bang & Olufsen, for example: The over-ear H9i costs $499, while the on-ear H8i is $399. Compare those with the wireless in-ear E8 and E6 options, each of which sells for $299. Again, this isn't gospel, but it may help you decide if you're considering various models with different wear styles.
Wear style also contributes to overall comfort. Again, your personal preferences will vary, but there are some things to consider. A lot of wireless or true wireless earbuds don't come with cushiony foam tips, which makes longer listening sessions a chore. Personally, I find cramming those in my ear will only ever be so comfortable. For hours-long streaming marathons, I reach for a pair of on-ear or over-ear headphones.
With the more traditional models, there are two key things to look at: headband tension and ear pads. If the headband is too tight, the headphones will feel like they're pinching your head. That might be fine for a few minutes, but after an hour or so, it's pretty terrible. In terms of the ear pad cushions, there's a fine line between too soft and too firm. If the pads are too soft, you could feel the rim of the ear cup pressing in around your ear. And if they're too firm, overall comfort will likely suffer. Of course, you might not always be able to judge these things before making a purchase, which leads me to my next point: the test drive.
Try before you buy
It may seem obvious, but if you can find a retailer that allows shoppers to test-drive headphones in-store, take advantage of it. It's much better to try on a pair at your local Best Buy, Target or other shop to confirm your decision ahead of time rather than get something you ultimately won't be happy with. Save yourself the trouble of having to ship them back. This can also help you determine whether on-ear or over-ear is better for you, even if the exact model you're eyeing isn't available for demos. Just don't expect to try a pair of wireless earbuds at a retail shop, because ... ew.