The rule that I use is that the bigger the size of the headphone, the bigger the need for amplification. Of course factors like driver sensitivity and impedance will matter, but the general rule of thumb is, use a dedicated headphone amplifier for a full size headphone. Even a portable amplifier can be enough, depending on the type of the headphones.
Time to invest in a new set of headphones? It’s a hugely crowded market with hundreds of models to choose from, so here’s a handy timesaver: The Sony WH-1000xM3 are the best headphones. In fact, their combination of top-notch audio quality, superb noise cancellation, and dependable wireless performance is such a strong formula, we named the WH-1000xM3 the best wireless headphones and the best noise-canceling headphones, too.
I tend to regard the M50 as the minimum for hi-fi listening with no apologies for limitations. But if you have to go cheaper than the usual $125 USD for the M50, the B&O Form2 with a simple bass boost gives a real hi-fi sound, and it should be available for about $100. The Beyer DTX-501P (similar to soundmagic P30) is good for $100, but needs a slight treble boost. The LSTN Fillmore with wood cups is somewhat colored, but still a good listen and good for $100. Below $100 are the Sennheiser PX series – not hi-fi by any means. There are several good IEMs below $100, and Apple Earpods with a Dirac or Accudio Pro player are very hi-fi, and cheap.
What I’m saying here is that it’s better to own three $100 headphones than one $300 headphone. Or three $300 headphones than one $900 headphone. Why? Because most people don’t limit their playlist to strictly one genre. And following the logic from Rule #2, the right headphone-music pairing is going to be better than one expensive headphone paired to the wrong music.