Start with form factor
The first decision is the shape of the thing. Over-ear headphones wrap around your ears and are generally the most comfortable for long sessions. On-ear models are smaller but press against the ears, which some people find uncomfortable. In-ear earbuds disappear into a pocket but sit inside the ear canal, which others dislike.
There is no objectively best form factor — only the best one for you. If you will wear them for hours at a desk, over-ear comfort usually wins. If you carry a small bag on a commute, earbuds win on portability.
Comfort beats every spec
A headphone with perfect sound is worthless if it hurts after 30 minutes. Pay attention to clamping force, ear cup depth, and weight. For earbuds, the fit of the tips matters most — a poor seal changes both comfort and sound dramatically.
If you can, try headphones on before buying. If you cannot, read about fit from people with a similar build to yours, and buy from a retailer with a reasonable return policy.
Connectivity and codecs
All modern wireless headphones use Bluetooth, but the supporting details differ. Multipoint lets you connect to two devices at once — handy if you switch between a phone and laptop. Codecs affect audio quality and latency, and the codec must be supported by both the headphones and your phone to matter.
For most people, a recent Bluetooth version and reliable pairing matter more than the codec alphabet. Latency only becomes critical for video calls and gaming, where a noticeable delay is annoying.
Battery life, in practice
Manufacturers list battery life under specific conditions, so treat the number as a ceiling rather than a promise. Real-world use — calls, higher volume, cold weather — shortens it. Look for a battery life that comfortably exceeds your longest typical day, and check how long a quick charge buys you.
USB-C charging is now standard and worth insisting on, simply because it means one fewer cable to carry.