Over the last decade, I've had the privilege of testing and reviewing dozens upon dozens of Bluetooth audio headsets. From big over-ear headphones to tiny in-ear buds, from powerful active noise cancellation to open-ear bone conduction, I've had enough experience with nearly every form factor out there, but no matter what the design, materials, features, sound, or price are, I keep coming back to one conclusion: the best headset is the one I can wear comfortably.
Like any other gadget reviewer out there, I tend to get a little too focused on the spec sheet when I'm trying a new headset. During my entire review phase, I try to be as objective as possible and cover every aspect. I touch on comfort a little, but that factor is so personal and depends on your head or ear shape so much that it's pointless to dwell on it. And it's near impossible to base an entire recommendation on it. What works for me may not work for you, and vice versa.
But after the words are written, the photos taken, and the review published, comfort becomes the absolute most important factor for me. Every other point falls by the wayside because I can't use the most popular, highest-spec'ed, most bells-and-whistles headset if it's uncomfortable for me. In other terms, the best headset is the one I can actually wear for a few hours without wanting to rip it from my ears / off my head.
The best headset is the one I can actually wear
That's why, on my desk, you can still find the Plantronics BackBeat Pro 5100 (my review), a pair of Micro-USB buds with a relatively average battery life and no ANC, despite me having reviewed plenty of USB-C buds with ANC and better longevity. The Pro 5100 are by far the most comfortable true wireless model I've tested. They're so incredibly tiny, so light, and most importantly, they don't exert any pressure on my ear's tragus when worn. (Throughout my reviews, I've discovered I have special ears with a very sensitive tragus.) I can easily keep them in my ears for hours without pain, a feat no other bud has accomplished so far.
The other pair I'm still using is the Anker Soundcore Liberty Air 2 Pro (my impressions) because they're the second most comfortable buds I've tried. There's ANC here, USB-C, wireless charging, and enough cool features to justify sacrificing the extra comfort, especially in crowded trains or loud areas. I wish I could make that same comfort concession for the Sennheiser CX 400BT (my review). Unfortunately, I can't wear those exceptional-sounding buds longer than an hour, which relegates them to very occasional use. My husband has no issue with them, though. Sad for me, good for him.
This applies to headphones too. It took two failed attempts for me to realize that on-ear models are just not my cup of tea. It's over ear or bust. On top of that, the oval-shaped earcups are a much better fit for me — the rounded ones end up pushing and hurting my ear instead of fitting around it. But the most important factor remains the headband. Too wide or too stiff and it'll be the end of me. No amount of high-end features can redeem that pain.
No amount of high-end features can redeem that pain
Two pairs of headphones have hit the sweet spot for me so far: the famous Bose QC35 (my review) and, surprisingly, the Marshall Monitor II ANC (Stephen's review). Maybe I shouldn't be surprised, though. Both of them have a very similar design, with a headband that marries the shape of the wearer's head, lots of joint flexibility, and super comfy oval cushions that wrap around the ears. I can wear either of them nearly all day long without getting a headache and without getting sweaty. For many years, my heart swayed to the Bose, but with USB-C and ANC, the Marshall are currently winning the fight. I wouldn't have given them a second thought, though, if I had to compromise on comfort one bit. After all, I'm going to work for several hours with these on, so I have to actually be able to wear them for several hours.
It feels a bit awkward to say that the one factor that should matter in your buying decision when it comes to Bluetooth headsets is one we really can't help you with at all. We can write thousands of words about a specific model and you can read them, then proceed to read thousands from other writers, then watch some YouTube reviews, but nothing will compare to you actually trying them on and seeing if they work for you. Design, materials, sound quality, features, battery life, and price are all secondary to that.