Think of it as sharp vs round transients. Most headphones have round transients especially planars. Sharp sounding headphones are like Focals.
Also worth to mention that some people use the word square to describe how digital the sound is, especially the treble (how close is it to 8bit sound of older games) .
I personally define square/round as hearing overshoot/undershoot when each note starts to develop from zero stimulus. Or which side reproduction is closer.
It could also be a direct reference to sine waves vs square waves. If you've ever heard a square wave, there's a distinct feel to it. Music that hard clips also comes out kinda square-ish.
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