First up, how much do you hate wires? If you're looking for cable-free listening, you'll want some Bluetooth-enabled 'phones. It's worth considering battery life - Bose's QC35s can do a full 20 hours on a single charge.
If you'd rather have the certainty of a cable, be sure to check it's compatible with your device. Own an iPhone 7? You'll need some Lightning-equipped headphones, then.
Once you're plugged in, you'll probably want some noise cancelling tech, too, to keep the outside world, well, out. Effectiveness varies across models, with both passive - literally blocking the sound - and active - using microphones to measure and counteract noise - approaches.
As for comfort, the in-ear versus on-ear debate is really a matter of personal preference. If you have toasty lobes, buds might be better. If you prefer not to jam silicone tips into your hear-holes, on-ears are the right choice.
Cost: spending more doesn't necessarily mean you'll get a better listening experience. Primarily, this is because we've seen a proliferation of low-price, high-quality headphones in recent years. Then, there's the fact that audio quality also depends on the device that's sending it. Properly expensive 'phones deserve audiophile-level kit.
Of course, none of this matters if you're buying new cans as a fashion statement.
Here are a few of our favourites choices.
The best 'buds we've tried for the money, these in-ears from SoundMagic possess a price tag that belies their fantastic sound quality. Bundled with an array of tips, the E10C offers bold bass, clarity and full-bodied sound.
Buy the SoundMagic E10C for £44.95 from Amazon
JBL Everest 100
JBL’s brand new - beautifully shaped wireless buds are designed for a snug fit. Offering eight-hour battery life and built in microphone with echo cancellation technology providing more natural sounding voice calls. Along with weighty bass make them a great choice for gym-goers and commuters.
Buy the JBL Everest 100 for £59.99 from Amazon
Soul Electronics Flex
Simple decent quality along with decent sound, the flexible, water-resistant design of these Flex 'phones makes them a boon for active listeners. A light, flat cable doesn't bounce too much, whilst very handy ear hooks mean the buds stay in as you run.
Buy the Soul Electronics Flex £24.55 from Amazon
Bowers & Wilkins P7 Wireless
Wireless without compromise, our favourite pair of high-end cans has gone Bluetooth - without losing its stunning performance. They still look great and truly easy to live with, B&W has made in the P7 Wireless a premium listening experience without a downside.
Buy the Bowers & Wilkins P7 Wireless here for £319 from Amazon .
Bose QuietComfort 35
With loads of battery life, Bose's QC35 don't offer the best 'bass' sound on the market - but that's the point: they're tuned to stay neutral, so you'll only get clarity. Ideal for the commuter who doesn't need to bounce off their seat.
Buy the Bose QuietComfort 35 for £329.95 from Amazon