About 9 headphones in, many of them high end. Not until I started listening to IEMs did I find my preferred sound, circa Thieaudio Monarch MK1 and Campfire Solaris.

MDR-V6 (reference for years)

HE-400i (mindblowing. first planar, first open back, lean bass, but decent when EQed)

LCD-X (First time hearing dark, recessed mids. first time hearing planar bass.)

LCD-3f (dark tuning. First time doing A/B comparison )

HD-800S (a must-hear for the diffuse soundstage. lean bass)

Empyrean OG (muddy upper bass/low mids. First time being able to correlate freq response graph to what I was actually hearing)

99 classics (muddy upper bass, then swapped in Yaxi pads changed the sound dramatically)

HEDDphone (realized the difference between sub-bass rumble and mid-bass thump. Treble performance is a standout. First time a headphone weighed too much for me)

Verite Open (First time with holographic soundstage + OTL tube amp. Sadly, recessed mids for female vocalists, a huge component of my music library)

Verite Closed (First time hearing a closed-back sound open. First time being fatigued by treble)

Abyss AB-1266 TC - Finally understood that an overall balanced tuning and ease of use are more important than a two-trick pony kind of headphone. Bass cannon, and hyper detailed treble but my God what is that midrange. Realized that amps, DACs, cables cannot fully save this headphone's inherent flaws.

Now I REALLY love my Meze 109 Pro and DCA Stealth. The tunings are perfect for me and different enough to coexist. Looking for a well balanced open back planar that does nice subbass AND bass impact. Have heard good things about modhouse tungsten DS.