I’m not sure you should “cheap out” on headphones per se. The really cheap ones are usually horrible, both in terms of sound quality, usability and comfort (well, except for wired Apple ones, allegedly, though they never fit me right). It’s just that it makes no sense to go for really expensive ones, unless you’re really into audio and love hearing the tiny sound reproduction differences between them, or enjoying the different tech etc. The middle ground of $50-$100 for in-ears and $100-300 for over-ears will often offer you good/great/excellent sound quality and the same usability&comfort as more expensive ones.
I’m not sure you should “cheap out” on headphones per se. The really cheap ones are usually horrible, both in terms of sound quality, usability and comfort (well, except for wired Apple ones, allegedly, though they never fit me right). It’s just that it makes no sense to go for really expensive ones, unless you’re really into audio and love hearing the tiny sound reproduction differences between them, or enjoying the different tech etc. The middle ground of $50-$100 for in-ears and $100-300 for over-ears will often offer you good/great/excellent sound quality and the same usability&comfort as more expensive ones.