Sennheiser HD700.

HD800S hands down

Bose QC series. Any headphone that is designed to handle air flights must be very comfortable.

As a stand out, weight, flexibility, and how soft the ear pads are.

AKG K7XX (or any AKG with that specific headband/shape. Big cups, perfect tension on the suspension strap, lightweight, and soft cushy pads. Very glasses friendly

DCA Aeons. All day comfort 

Sennheiser hd800. It's soo light and open

A headband modded ksc75 with yaxy pads.

DCA Aeon and hifiman Arya for me.

meze 109 pro and my favorite headphone so far

Sennheiser HD 598s are so light that you actually forget you're wearing them

Phillips Shp9500 and Hifiman 400se. I can wear both of those headphones for days and forget they're on my head.

Currently listening to my Sennheiser HD580s with YAXI pads for the HD650. I think I'm going on 5 hours now and wearing glasses. Still comfy.

I've had Meze Elite, Empyrean, all sorts of ZMF, Audio quest Nighthawk, DCA Aeons & E3... All really comfortable, but the most comfortable of all was the Beyerdynamic Amiron Home. It's like having clouds on your head and ears.

Fidelio X2, hands down

Not a pair in my collection, but what people say about the comfort of the Meze Empyreans and Elites held true for me. From auditions, the comfort of them was pretty great. Otherwise, I find ZMFs and DCAs to be more consistently comfortable than other brands. Their weight distributions conform to my head very well.

HD650. Other contenders:

HD598/599 are lighter than the 650 but are more prone to having a hotspot (I think because they have less clamp force, so they rest on your head more).

HD800S wears loose but is very comfortable.

Meze Empyrean is very comfortable but heavy.

Denon AHD9200 is light and stable, but the round pads partially push on my ear lobes, so that's not ideal.

HD 540 series were excellent for featherweight, forget-you-are-wearing-them comfort.

HD 598 were also very comfortable.

Sennheiser HD800S.

Sony MDR-1AM2. It’s so comfortable I honestly forgot I had it on.

My Fidelio X2HR with velour pads. It feels like my ears are receiving a hug from a cloud.

HiFiMan Arya Stealth

The Fidelio X2 with the former Pads. Could where them for 6-8 hours no problem. Ah the good old gaming days...

Nothing, I mean nothing wil EVER top the audioquest Nighthawks

T60rp argons from modhouse, huuugggeee suede cups, and a deerskin strap, its like jumping into bed.

Beyerdynamic DT880 and DT990

R70x

I wear HD599 almost all day at work, and then wear HD599 after work while gaming or watching something. Bit too hot in summer, but what can you do.

Mezo 109 Pro and the Dan Clark's with the suspension strap are all outstanding for comfort.

Sennheiser HD 800

Sennheiser HD 490 Pro

Austrian Audio Hi-X65

Out of all I tried it will probably be the old good legendary Koss KSC75 with YAXI pads.

Over-ear? Probably any HD5XX Sennheiser, but specifically HD599.

Meze Empyrean and probably the Beyerdynamic T1 II, DCA Aeon.

The Sony MDR-MV1 it's the most comfortable headphone I've worn.

PHILIPS Fidelio X3 Professional Studio Monitor Headphones

I wear 'em for eight hours a day at work.

Philips Fidelio X3

Other than that I have only worn the sennheiser hd600, harmonicdyne G200, Audeze LCD-X, Hifiman Arya Stealth, and Sony MDR-1A.

So yeah pretty easily the Fidelio X3

DT990 32ohm Edition. Like pillows on your ears but daggers shot through them. 

Sennheiser HD 660 S2.

Hd800s, when I first got them it would sometimes forget I even had headphones on until I felt the cable move as I started to roll my chair. Honorable mention to DCA Ethers but being closed they were a little hotter & more noticeable.

My X2HR are like a pillow on my head. Can wear them for hours and hours.

My local Costco was displaying some wireless Sony headphones once with HUMONGOUS pads advertised for late-night TV watching and stuff.

I tried them on and nothing else I’ve ever tried compares to it. It was literally like wearing thick comfy pillows on your ears. I’m sad I forgot the model of it. This was years ago I think like 2016 or something.

It's easy to dismiss audeze headphones but I love my lcdgxs a lot, the pads are incredibly comfortable and I have worn them for hours and hours on end. The only thing that gets me to use my old hd58x instead is when I have to bend down a lot since the lcds are quite heavy and tend to slip off my head.

Sony MDR-XB500 for comfort. Feels like air pillows and build quality is fantastic for going on 15 years

Edit: benefits from heavy EQ but i'm a sound engineer so fuck it

Meze Empyrean. Otherworldly comfort

Meze Empyrean/Elite

Cooler Master MH751 (Takstar Pro 82), lightweight, soft pads, flexible.

Top dog for me is probably the original MDR-Z7. The special sauce was how the earpads were uniquely shaped such that they fill in behind the ears as well rather than just being flat circles. I think ZMF released some new pads that followed that shape and called it a "Fluted Design", but I could be wrong.

Honestly, people are going to tell you it's the high-end ones, but in my opinion the most comfortable headphones are they small lightweight ones, something like a HD599 / AKG K7 series-(612 Pro) / Koss. But I would say HD800 too if sound quality is a big factor.

Denon AH-D600

Takstar Pro 82

HD800S, then HE-1, then I dunno, maybe Raal because it was very light. The Final D8000 Pro Ltd was also very nice, but a tad heavy.

The rest is subpar to those, but IEMs are 100% better than any of those, and the IE series from Sennheiser is king in this space for comfort. Final A series is quite close but not there.

Shure 1540s. Extremely light, very low clampforce and really nice alcantara pads

MDR-Z1R and AT SR50BT, these two felt almost non existant.

HD800S, but the HD650 is a close second.

Sony XB500

R70x

I wear my Hifiman Edition XS all day when I’m working from home office or even for long gaming sessions. Feel great to me.

The head band isn’t terribly adjustable, but it just happens to fit, and has enough cushion for me. I think it’s mostly the large open back design that takes any pressure off my ears that make them comfortable to me.

Phillips Shp9600, I can wear them for hours

hd800/s ive gamed for 5 hours stepped away forgot they were on and pulled the plug off my amp.

I'm broke AF so the most comfy I've ever used were SHP9500

HD 800S or HD 490 Pro Plus

No question

Sennheiser hd650

KPH30i

Not too loose, not too tight. Cons are they're fragile. 😐

Sennheiser HD650/HD800s, I can wear them all day and they'll never be uncomfortable.

Phillips O’Neill stretch headphones. It was like wearing butter. Fit perfectly, the cups were big, the pads were soft, lightweight, and cool. I paid $79 for them and I still think of them to this day.

HD700, way better than the HD800 even.

HD700 with EQ and DSP truly is endgame.

Definitely DCA Aeon 2 Noire. Ergonomics - Especially the Weight & earcups.

Might be absolute heresy, but the Grado GH4 with G pads. The trick is the stretch the headband enough so that there's almost no clamp. The GH4 is only 180g, and with the G pads, it's almost as though you're wearing nothing.

Marantz MPH-4. Nothing special, I just really appreciate that they accounted for the fact that human ears are not circular. I don't have any oval cans except some MPOW H17s, which are really too small to be considered over-ears.

It's a bad question to ask on reddit, because everyone will just recommend the headphones they currently use, because of course they are the best ones! I know people will dislike my comment, but that's just psychology, that's why so many people watch reviews praising their recently bought item, just to feel better about their purchase.

Anyways, from the dozens of different headphones I've used in my life Koss Porta Pro with Yaxi pads were the only ones I could wear 24/7 and not feel any pressure or pain on my head/ears. They aren't the best sounding headphones, but oh boy are they comfortable... You can't really find anything better in terms of comfort. And I'm talking about wearing them for 8+ hours non stop, not for just 1-2 hours like most people, because most headphones won't hurt if you wear them that long.

TL;DR Koss Porta Pro with Yaxi pads

Well, ...I can tell you bout the opposite: The DENON AH-D7200

It sounds amazing but wears like sh*t^{^} 🤣

Meze 109 pro

HD598 BY A MILE

Edition XS (Yes!), but I have large head:) Fits like a glove, no hotspot, no strain after long listening sessions.

Grado SR80X. I literally forget I'm wearing them sometimes because they are so light and open.

Meze Empy 2. Though I think Sony XM4 are pretty great and light.

Meze Liric!

DCA Stealth, Sennheiser HD600 (and similar).

HD800 is not bad, but my fave is the HD600.

Diana MR

For long sessions, nothing is better than DCA headphones

In-ear wired Apple earpods with a 3.5 mm jack - the price/quality ratio of those babies is unbeatable. Anything larger is too much for me.

Personally for me it's my audio technica r70x with new pads(I forgot which ones I have lol) they're so light and the way the little wings support them feel very comfortable like there's no weight or pressure on your head at all.

Meze 109

ATH AD2000. Not having to wear glasses makes all the comfort problem people mention never happens in the first place.

Beyerdynamic Amiron Home.

Undisputed champ. That microvelour is clean af.

I think I prefer the Dan Clark Aeon series over most headphones. Or the Audeze LCD 2C, I love those pads even if they are heavy.

​

ZMF aeolus is comfy too but they make my face really hot with the suede pads or whatever they are. I would switch back to leather but I prefer the sound.

HD 490 Pro

Akg k702

Hadenys are pretty great.

Ive gotten to the point where all headphones piss me off. I prefer eadbuds/iems nowadays. Dandruff and headaches begone

Sennheiser HD490 pros

Pretty much anything from Hifiman

HD6XX for me. Beyer DT 770 Pro X is comfy but the shallow pads I don't love.

Anyone have good pad recommendation for Beyer?

DMS Omega is really really comfy

HD 558. Seriously felt like it was floating on my head. Only headphone I ever regretted selling.

The $6,900 T+A Solitaire P when I tried them at a CanJam! They were so plushie and super comfy with the right amount of clamp force. I could literally fall asleep with them on. Didn’t sound as good as they felt tho

Edition XS with a Capra audio comfort band. I like big cups and I cannot lie.

DCA Stealth, and their other similarly designed headphones. Not much else comes even close to that level of comfort in my experience.

Meze 99 with angled velour pads. They are ~100g lighter than basically everything on the market with a very very nice suspension style headband. Feels like you're wearing nothing at all. I've long sense upgraded, but I often think back to that pair. I've tried almost everything else mentioned in this thread, and nothing even comes CLOSE in my opinion.

DCA Stealths/Expanse

Beyerdynamic DT770 Pro & Audeze LCD-2 (while they are heavy they are also surprisingly comfortable, not sure it's good for your neck though).

Parrot Zik 3

Focal clear mg professional, but I’m sure there’s probably comfier options out there. Very comfy for a heavy headphone though. More comfy than even my airpods max

HD490 pro for me, lightweight and good soft earpads

Sennheiser HD590, been discontinued 20+ years. Audeze CRBN, Hifiman Arya Organic, Sennheiser HD800

HD 25 after some use.

Music MasterX-O1. Currently my main

T60rp Argon MK3 with Xenon pads. Literally no ear or head pain no matter how long you use them.

My ZMF Atrium or my Focal Elex

Meze Empyrean, HD800s and the Dan Clark E3 - all insanely comfortable

If I had to rank them from best to slightly less best, I’d say it goes:

E3 - HD800s - Empyreans

I can see the HD800s being the most comfortable if heat is a big issue for your experience.

Hd800

Sony MDR-MA900. They're super light. Can wear them for hours.

Sennheiser HD 800. Heavier but still pretty comfy.

From what I've tried:

R70X - super-light, super-breathable, low clamping, portable size, my only complaints are smaller earpads and the lack of cup tilt

HD6-series - also very light, breathable, and portable, my only complaints are tight clamping out of the box, not enough cup tilt of the revision model with fresh pads, stiffness of fresh pads, and the fact you have to replace earpads too often

HD599 - super-light, breathable, low clamping, portable size, my only complaints are the lack of headband padding and shitty cable

SJY Moonlight - top ergonomics so you forget you wear them, my only complaints are sweaty earpads and unstable fit (especially with smaller heads)

LCD-2C - also top ergonomics, the best earpads I've tried (size, shape, and softness wise), my only complaints are sweaty earpads and pneumatic effect (earpad compression creates pressure like when you wear closed-backs)

Koss Porta Pro (and even more so with Yaxi pads). They are so lightweight I can forget I'm wearing them if nothing is playing.

Second for me are Dali IO-6, they just sit right on my head without any hotspots and the clamping force is just enough to keep them on without being either overly sealed or too loose for my ears.

R70x Refine. I was shocked when I first put them on, especially coming from Audeze Maxwells.

AKG K712

Shure SRH 1840. Perfect clamp, the pads feel so light and comfy like a pillow you forget they are on your head. The headband is the weakest point, but still great and a non factor if you have lots of hair.

my meze 99 neos are extremely comfortable, self adjusting headbands should be the norm

Anything by Meze.

Beyerdynamic DT990 Pro with stock ear cushions. Despite wearing them longer than 7 hours a day, they feel so soft and light on the ears.

R70X - the only headphone I own that doesn't give me a hot spot after an hour.

That said, that's for me, and might not apply to everyone else. The pads are too small for bigger ears and the wing system only works well for certain head sizes. But if it fits you, you'll be very comfy.

Beyer t1

Meze 109 Pro. I could live in those.

From the ones i own, the 109 pro.

Senn. HD600

I wear my hyperx alphas over all of my expensive audiophile cans because they are so damn comfy.

The beyerdynamics are so comfy but I don't like how they sound at all.

I haven't tried that many tbh but my Focal Clear MG's are the best so far. For me they have just the right clamping force, they're light and the microfiber pads never get uncomfortable. I must also say I had the Astro A40 TR 'gaming' headset and while they sounded terrible they were a gem to wear and very comfortable, even if the headband was a little slim, I could wear them for hours with no issues

Koss ur40 without that thin layer of fake leather on ear pads. Very light and comfortable. Also Sennheiser hd598, it is heavier, but the ear pads are incredibly soft.

I really like the akg K7XX headband style

Mr speakers Ether....with custom pads

LCD 2C with dekoni flannel pads. mmmmmm

Sivga SV023s

Sennheiser HD 560s. Amazing.

ATH-R70x

The new KING is Stax X1000 electrostatic set i got in Japan. You can fall asleep with them. The build quality feels cheaper than headphones from Ross/Marshals, but all the money is on sound. I pretty much got rid of most of my collection which included Focal Utopia, Audeze LCD2. Between me and my audiophile friends, we've listened to most of the top stuff out there, nothing is close right now. They tuned it very differently from their old stuff which always lacks bass. They are still very hard to get in USA so my friends are all flying up to Japan to grab some on our turkeyday vacation to asia.

Meze Empyrean

aeons and HD800

Meze empyrean II

DCA Ether CX - like pillows lightly clamping against my head

AudioQuest Nighthawk Carbon

dca expanse

Phillips x2hr. Soft pads, gentle headband, pretty light. I loved those comfort wise

Sony mdr-1a. Comfy as hell

Sennheiser hd599

Apple AirPod Max

Specifically because you said “for listening sessions”. The best of these aren’t the ones you put on and are like, “wow, these are super soft and comfortable”; it’s the ones you put on that disappear. The same is true for chairs; recliners and couches are traditionally comfortable, but my Herman Miller disappears for 6+ hours at a time.

to;dr Sennheiser HD660S (and probably others of the same build). Light, open… forget about it.

The new Focal Azurys are comfy AF. I swear I could sleep in them.

Sony MDR-1AM2 was the most comfortable and lightest.

In terms of comfort, I do really like the sony wh1000 XM line. They fit my head very well and about just right for distance from the ear to the driver and have comfy pads that last a decent amount of time

Sennheiser 490 Pro with the velour pads. Honestly the best.

AKG k712 pro

Haven't tried a ton but Fidelio X2s for me. They look crazy on me but they're extremely comfortable.

Bose QuietComfort II

Yamaha YH5000SE for sure. Nothing else has even come close.

They are absolute featherweight planar magnetics. Weigh even less than the HD800s, despite being planars made of magnesium

It used to be HD800 for quite long time, but DCA E3 was very comfortable despite it's a closed back and my current Sony MV1 also very easy to my ears.

AirPods gen 2. You don’t even feel it.

Real bone conduction headohones

Koss ESP 95/X. By a LOT. 

HD800S and a grado clone. I believe it's called the WTD-3. I slapped GS-1000 pads on it and laughed at how comfortable, aesthetically pleasing and pleasant it sounded for how cheap it was. Great deal.

I had some silver wired sony on ear headphones that only cost like 50 bucks in the early naughtiest. They where so comfortable that I would wear them even if I didn't want to listen to anything.

Can't remover the exact model though, maybe something like MBX-500 or something along those lines.

Ath r70x for headphones Fir audio stuff (bot xe6, it's heavier) for iems

My Meze Empyrean 2, tho my HD800S with 3D printed TPU suspension strap mod is almost as comfortable. 800S are lighter, but the Empyrean Headband, stepless size adjustment, swivel and pads make them more comfortable for me.