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How many pairs of headphones do you need to cover all situations?

I have three: Sennheiser IE 800's for OTG; HD 800's for use for most situations (movie watching, most classical and some jazz orchestral), and Audeze LCD X's for smaller jazz ensembles and most classic rock. Everything get's Eq'd, the big phones are listened to with the Smyth A16 Realizer which has in person, 24 channel PRIR's for Dutch & Dutch 8C's and Kef LS 50 Metas+SB 2000 sub.

Definitely feels to me like all the bases are covered.
 
I hate IEMs. I have one open (Audeze LCD-3) and one wireless (Apple AirPods Max). I only listen to headphones occasionally. When I listen to music I normally use my stereo speakers.

Martin
 
When outdoors I wear seasonal varieties of brimmed hats. Here's my cool weather soft headgear slightly compressed by my old AKG K301 120 Ohm headphones.

The K301's head suspension band was cut off and so now the metal connecting arch (between left and right ear cups) rides directly upon the hat fabric. This changes the apparatus alignment allowing the ear cups to pass beyond the hat brim to embrace my ears.
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Headphones worn in bed often press uncomfortably against my head because of altered alignment due to the weight of my head compressing the pillow center and displacing pillow mass laterally. Here's my old Yahama YH-100 150 Ohm headphones I use when lying down.

The small diameter cups will rest on the ears and independently swivel so that I can keep their respective cables pointing away from the pillow; their narrow ear cup profile doesn't appreciably push sideways into the pillow. Being able to freely rotate the ear cups once head sunk into the pillow means the wires don't push against anything, and if I fall asleep should my head loll off to the side the junction of a cable with it's ear cup is not compressed/flexed against the pillow's bulk.

Modified inside their ear cups and with soft leather atop thin original pads plus handmade thick head cushion these old planars are enjoyable. Late night sessions often turn into "just one more song" marathons.
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For listening to headphones on the streetside front porch I put this HiFiMan HE-350 19 Ohm on a looong cable for dragging outdoors. Plugged into an old Yamaha R-5 amplifier that has dials for loudness, bass, treble, balance, and volume allows these comfortable fitting open back headphones with surround the ear cushions to sound good amongst the ambient noise.
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Food market shopping stateside USA during the recent pandemic required wearing a face mask inside and this pair of Koss TBSE1 38 Ohm headphones were easy to slip the loops of a mask on and off over the earcup side pivots. These adjust comfortably as well and remain my going to the supermarket pair.

This is Koss' Tony Bennett signature edition and the ear cups swivel flat like DJ 'canz making them convenient to interact with people in public. I have not only re-cabled and modified inside the ear cups, but also drilled the cup backs into semi-open covers. They are lightweight even with the leather glued atop the head band as well as on both the front and back of the ear cups.

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Walking the dog for the last time in a day while streaming 246AAC over an iPhone paired with a portable amplifier I wear my old AKG K240 "sextet" 600 Ohm headphones. These are modified inside the ear cups and re-wired from single to dual ear cup cables; I had to zip tie headband into adjustment.

I wear eyeglasses and have made these comfortable since the leather ear pads' size is large enough to go around my ears. I've packed gauze underneath the ear pads and that plumped up pads up creating enough space so the ear pad doesn't forcibly push against the eyeglass arm resting across my ear's ridge.

Photo below is just to show why the old K240 got nicknamed "sextet". Inside the ear cup one can see the outline of some small round discs underneath the ear cup grill. There are six (a sextet) of those arrayed around the arc of each grill cup.

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Lastly: Walking is my exercise and I've headphones suitable for weather during morning and mid-day dog walks, as well as forays. Ambulation music is usually just from MP3 source on an old iPhone that I can equalize somewhat.

When out door temperature is mild I tend to prefer a vintage Fostex T20 semi-closed back 56 Ohm planars with a portable amplifier. These are moded inside the ear cups, re-wired for cables of both drivers coming out of their respective ear cups and the old slack headband zip tied into alignment. Sound is very good and I've put soft leather atop the original exhausted ear pads.

In warm weather, as air heats up with the day, I'll use a lightweight Beyerdynamic DTX-800 open backed 32 Ohm headphone. They're modded inside the ear cups and re-wired for cables of both drivers coming out of their respective ear cups. I swapped their ear pads and put some pleather pads on that go around the ears; these are very comfortable for the eyeglasses I wear.

Once it's really hot out doors I use the retro-looking Bang&Olufsen Form2 30 Ohm headphones with their little rectangular foam pads that sit lightly on the ears. These sound more rich than the design indicates, and don't make my ears hot out on walk-abouts.

When it's cold out of the house I use Sennheiser Momentum 18 Ohm closed back headphones. These are also practical for public transportation, like on auto-busses and airplanes which are noisy. They go on the ear and have so much clamping force my eyeglass armatures press uncomfortably against the ear cartilage during prolonged wearing.

A closing tip: Because I wear glasses when outdoors I put on a brimmed hat to control glare; usually one that looks like a baseball cap having a front brim. To get the most stable headphone headband position over the cap I remove the ubiquitous button riveted up on the crown of the cap. Removing that little button (simple pliers squash it loose) not only removes it from being pushed into the skull, but allows positioning of the headphone's headband farther forward - a muuuch more comfortable fit is the benefit.
 
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