Audioquest Nightowls are the most comfortable headphones I’ve ever worn - period, not even close. Weird, hate-it-or-love-it tonality, but takes EQ extremely well. Perfect marriage with the Qudelix 5K.

Blue Ella are some of the most unique planar headphones you can experience. They come with a built-in rechargeable amp, which means you can drive them on anything. They’re fairly comfortable to me, but the unorthodox design means YMMV. Pretty neutral, warmer with the on-board amp.

Neither of these are made anymore, as both Audioquest and Blue left the headphone game. If you can pick these up for $200-300 on the used market, I’d recommend them. Both retailed for $700 on initial release. I’d say they’re both about equal to the Elex/Ananda-tier of headphones in terms of technicalities, maybe slightly behind.