At work, I amp using a Dragonfly Red outboard DAC, which frankly, I like less than my old NuForce Icon2. (I would've happily stayed with the Nuforce, but Apple cluelessly bricked older "dumb amps" like the Icon2 when they "upgraded" their audio code in MacOS Sierra. Morons.) The Dragonfly just doesn't seem to add anything beyond the system amp.
On my Mac, I drive the external DAC using the Vox app because it has a parametric equalizer. On my i[Phone|Pad], I playback using the Equ app, which also offers para EQ.
I love the Denons. They enhance bass a bit and don't export my music enough to annoy coworkers. The Senn HD-580s are great, but feel a bit "cool" compared to the warmer Denons (due to the open cushions). But their smoothness is effortless; I can listen to them all day long. The NADs cut out surrounding noise really well and offer surprisingly good fidelity for such lightweight cans. I like the Westones mostly for their portability; their sound quality just can't match any of my full-sized cans and IMHO depend too much on a good seal from the triple flanges.
I also own Grado SR325Es, but could never warm to them. Their bass is substantially weaker than my other phones, though mid-to-upper reproduction is exemplary.
I got them because I wanted something that blocked external noise (I don't like the "pressure" feeling of active noise cancellation) and they came highly recommended from The Wire Cutter.
I consider them 'fine'. They're relatively comfortable for 2-3 hour stretches (after that, the lack of ventilation makes them start to get sweaty, even in cool rooms), they sound decent, and the build quality and carry-case are great.
On the minuses side, the clarity doesn't match my old Grado SR-80's, the noise blocking isn't as good as my Shure in-ear monitors, and the in-line mic is worse than what's on Apple's standard earbuds.
Bottom line, they're not worth the $400 price tag, but now that I have them, they're good enough that I'm not out looking for another pair.
I have to say, I'm not as impressed with them as The Wire Cutter review led me to believe I would be... and that has affected my opinion of The Wire Cutter. I probably could have bought a generic pair of closed-back headphones for $60 and been just as happy.
Over time, I came to prefer my audio to sound less fun and more "as is". Ie, without any spikes in the bass, mids, or trebles, from the manufacturer to colour the audio with some kind of wow factor.
Eventually, after a bunch of research and a $150-ish budget, I landed at the Beyer Dynamic DT250. They have the flattest EQ curve I know of, are super comfortable, and build quality is sturdy (Germans tend not to fuck around with the quality of the products products).
There's no excess wires that will get snagged around the can, and Beyer have their own unique cabling and connectors which are super-tough and chunky. Noise cancelling is average, but that's not an overly important feature for me.
If you want a bit more of a fun set with some more sub bass , check out the DT770. Supremely comfortable headphones and sound amazing.
Desktop:
Favorite - Razer Barracuda (with matching soundcard), great sound, super comfortable. (wish they hadn't broken)
Runner up - Turtle Beach Ear Force PX21 (just cause it says ps3 don't mean you cant use it on PC!)
Current - Razer Kraken 7.1 Chroma (1st gen, 2nd gen is more sturdy metal) (windows software sucks, but I use GNU+Linux)
Others I've used - Logitech G35(wired and wireless versions), Creative Sound Blaster WoW Wireless, Seihnheiser.
On-the-go:
Favorite - Yurbuds Ironman Focus Behind the ear (lost them recently, so sad)
Current - Klipsch R6i
Others - Multiple cheap skullcandy, new model Apple.
All that said, on-the-go I don't trust bluetooth so I don't do wireless, but if you do your options expand quite a bit.
One more thing to keep in mind, if you really want the best, go to a hearing aid place and get your earmold taken so you can get the perfect fit rubber exterior for whatever model you choose. Personally, I really loved my Yurbuds Ironman Behind the ears because they stayed on the best while lifting/running/yardwork etc. Most of the time when I select, besides form factor, I mostly base selection on frequency range. Which is how I ended up with the Razer Kraken 7.1 Chroma's despite how disapointed I have been with Razor the last few years.
When I was in the military the best pair I ever had was the Bose sound reduction headphones.
Also, the HD598s are easily some of the most comfortable headphones I've ever used, and I have a weird Kevin Durant lookin head - I used to get headaches and pain behind my ears after like 6 hours of wearing my old ATH-M50s but with the HD598s I've gone 12 hours and still felt fine.
I think the biggest question for choosing a daily driver headphone is whether you want to use a headphone vs. in-ear earphone. For my daily commute, I prefer earphones because they are less bulky, they don't warm-up my ear during the summer time, and I can easily take it off and put it in my pocket. For headphones, taking them off and storing them in my bag is so bulky that it is so damn annoying.
For long trips like air plane rides or bus rides or for in the office usage, I prefer headphones.
For at-home only listening, I use Grade SR80e, this is an open headphone and it is not great for commuting but awesome for listening at home.
Music Production - Audio Technica Ath-M35 / This closed-back pair is relatively flat. The pair puts more pressure on my ears so their not very comfortable for more than an hour or two.
On-the-Go - Panasonic Ergofit RP-HJE120 / This is an inexpensive V-shaped pair of IEMs that I typically throw in my pocket. Not the greatest when it comes to audio quality, but it does the job.
Both models have a special place in my heart now.
Also, bravo on the "daily-driver" pun.
My only wish is that I could wear them around walking, but they have a long coiled cable.
At work and on the go I'm using Shure SE215. Great isolation, clear sound and some of the best bass I've sampled from earphones.
I'd recommend both in a heartbeat and I think both of these represent good bang for their buck. Since I like my music (it's a hobby of mine) I wouldn't tolerate anything that I didn't think fell into the category of high quality.
At home, a Logitech G430 headset.
On the go, some in-ear bluetooth earphones from Aukey.
Sennheiser HD600 + Marantz PM65005 amp for home (open back)
Work:
Bose QC35 -- sound quality is somewhat compromised but the NC and comfort levels are second to none. Bose customer service is also excellent, particularly if you buy (and therefore can return/exchange) through a branded store.
Out and about:
Airpods, with foam covers. Without the covers, these were very convenient headphones that wouldn't stay in my ears for the life of me and so sounded thin and leaked noise. Then I added old-school thin foam earbud covers; Amazon sells some that are donut-style with a hole that exposes the light sensors, and they still fit in the charger. They don't compare to my audiophile headphones, but they sound "pretty good"--about on the same level as my SoundMagic E10s, maybe a little better. More importantly, now I actually will use headphones for 20-30 minutes at a time on walks, whereas before it was too much of a hassle to carry a fat case around, wedge them in my ears, etc.
Home, in living room:
MDR-1ABTs. I don't actually like these as much as I should for what I paid for them. The pads are thin and hurt my ears. But they do connect to my Sony sound bar using their LDAC low-latency/high-def protocol, so I use them for late night viewing.
Console:
Playstation Gold or Platinums. I have both. The Golds are more reliable about connecting to the dongle. The Platinums fit over my PSVR headset. Neither sounds great for anything but games, but they integrate tightly into the OS.
PC/Mac:
SteelSeries Arctis 7. No blinkenlights, and they sound very good for pretty much everything. They're comparable to my wired Sennheiser PC360s (basically a 55x/59x with a mic) but even cheaper. That said, buy the add-on leatherette pads from Steelseries--they make a world of difference for isolation and sound quality. They shouldn't sell these without those pads TBH.
Audiophil(ish):
Keeping in mind I like "fun" headphones and not monitors, I oscillate between Plantronics Backbeat Pro (one of the best sounding BT headphones I've heard with a phenomenal range and hellaciously cheap, but fugly and with round pads that don't really fit anyone), V-Moda M100s (add the fat pads to these too for comfort and sound; they'll last forever--built like a tank), and Master and Dynamic MH40s. (by far the nicest pair aesthetically with real leather pads, and they sound great if you can get a good seal, but I'm not a huge fan of cables anymore).
Gadgets:
I do have a JDS labs O2 amp+DAC setup. I use it with the M&Ds and the M100s sometimes since those are the two cabled headphones still in rotation. However, Apple headphone outputs have historically been good enough to not really benefit that much since all my headphones have lowish power requirements. Planars or some other "need a bunch of juice" headphones would be different.
The pros do outweigh the cons, IMO.
They sound almost exactly the same wired as wireless, which is to say very good assuming you don't mind a slightly dark and scooped profile. I listen primarily to industrial, rock, metal and heavier forms of EDM (brostep, drum'n'bass, hardstyle, etc.) and they sound wonderful for that. There isn't much hiss at all, which can be a real problem for bluetooth headphones due to the internal amp. I was impressed with the noise floor.
The bluetooth stack itself is another pro--handles multipoint seamlessly, which is actually kind of rare, and the range (with an iPhone transmitting) was at least 50 feet line of sight, and well over 30 feet with walls. At home I could roam anywhere, at the office I could get pretty far away.
While your mileage may vary according to source, I also found the BBP's latency perfectly acceptable even for light game playing (though it's not ~0, hence the Arctis). I think Crypt of the Necrodancer's calibration measured it around 150ms, which isn't bad for not being connected via a low-latency codec. I had no problem at all using them for movies.
One other point for the BBPs is the controls. One earcup has a ginormous volume dial as its inset and the other buttons are very tactile. While the dial does tend to stiffen some over time if you don't use them often enough, it's hands down the easiest set of controls to fumble to in a hurry. Plus there's a "talk through" button that pipes in exterior sound so you can answer colleague questions (or hear flight announcements) without removing them.
And, of course, the OG Backbeat Pros are around $200 cheaper street than Bose QC35s. If you have bluetooth you don't need the Pro+ with the dongle, and the Pro 2s [don't have a ton of improvements IIRC]*
In comparison, Bose doesn't sound as good. It does sound just like Bose, so if you know that sound, there you go. I find it acceptable but not phenomenal, and there's a little mud in the mid-bass I don't hear with the BBPs that unfortunately doesn't play as well with metal. EDM and industrial both sound fine. Bose does have just as good a BT stack in terms of seamless pair and switching behavior, but nowhere near the range. Latency is fine on Bose but I haven't tried them gaming.
Places where Bose clearly excels include the followup service--say what you want about the audio tech, but Bose's customer service is absolutely fantastic whereas Plantronics is average; the comfort--Bose headphones feel much lighter (without having weighed them both or checking specs) and comform to my face and ears better; and especially in the noise cancelling. Plantronics' noise cancelling just isn't great, whereas only the Sony M1000x have come near Bose in NC and they have some quality concerns.
* Edit: looking at Pro 2s, they do address the aesthetic and comfort issues, with ovular cups and plusher-looking pads, and are supposedly lighter. The really convenient controls aren't there anymore. They might be worth a shot buying from somewhere you can return them to if you don't like the audition, though if you're looking for great NC I'd skip right on to the Bose.
Sony is reportedly updating the MDR1000Xs, btw. If they can fix the headband-cracking issue they currently have, they should be a good combination of sound quality and ANC (for about twice as much as the BBP2s, so you're not missing out on anything by buying now!)
* The sound quality is excellent. Wired or wireless, the sound is sharp and crystal clear. But it's not particularly flat; there's a lot of midrange that makes it sound a little muddy. I've set up a custom configuration for the iTunes equalizer that helps with the (rock) music I listen to: punchy bass, clear treble, but less mud in the middle.
* The noise cancelling isn't bad. It does a great job on public transit but it's not as all-encompassing indoors as the Bose QC35 seemed to be, from the little I've tried them.
* The BB2Ps aren't nearly as ugly as the product photos make them look. They're not particularly brown in real life, just dark.
* They're pretty comfortable although I find it fatiguing to wear them for more than a couple of hours. The new over-ear shape looks like it made a big difference on the comfort level.
* The Bluetooth signal tends to cut out quite a bit from my iMac at home, which is pretty disappointing. It works better from my MacBook Pro at work -- not sure if there's some interference at home or what.
Overall I do like them, but I don't know if I like them enough to justify the $200 I spent. I haven't decided yet whether to keep them long-term. If I don't keep these, I might switch to the Beats Solo3 without ANC, or just bite the bullet and go for the Bose QC35...