Fellow headphone sad act here!
One of my absolute favourites right now is the Sony WH-1000XM3. I got them at launch in silver (why do people buy boring black all the time when there are colourful options?) and I use them pretty much daily.
For the commute they cancel out train noise. For work, they shut eejits out so I can work in peace. For the home, they connect to the soundbar so I can watch films late night and not disturb the wife and little ones. For music, they pair beautifully with my Pioneer XDP-300R DAP, especially for Hi Res, Atmos and 360 Audio stuff.
They are the most versatile and some of the best sounding cans I've ever owned. I love them.
Another favourite I keep at work are a pair of KOSS Portapro's. Iconic design, dirt cheap and a whopper sound from them, especially if you chuck 'em in to a headphone amp they absolutely SING! You know the best thing about them though? The KOSS lifetime guarantee.
Over time, the pads disintegrate so you need new ones. I've emailed KOSS twice now in the years I've owned these. Please can I have some replacement pads? No quibbles at all from them. Free shipping, direct from the USA. Exceptional customer service.
Legendary earphones that I will NEVER get rid of. They are that good and they are backed up with an amazing warranty. LOVE these.
Others in my collection include Sennheiiser HD598's in cream and walnut. These sound so good I can't bring myself to part with them. I have to use them sparingly though as they are open cups. I had a set of Grado's a few years back. Wish I kept them to couple with these. I'm semi-looking for a pair of Grado's...
Next is a pair of AKG 510's. They're like satellite dishes on your ears but they weigh very little yet sound absolutely substantial as heck! I really should wear them more than I do as the sound from these is absolutely BIBLICAL.
I have some Shure e3c and e4c IEM's. Never bothered to upgrade them because IMHO these were made when Shure IEM's were top dog only to perhaps Etymotic. Again, I should use them more often but I won't part with them, they are beautiful IEM's and both sound different enough to keep.
For running I use Aftershokz Titanium. Crap sound but they are perfect for long runs or those long 16 to 18 mile marathon training runs. Stick on an audiobook or podcast and enjoy while still being able to hear everything around you. Safety first!
I have a set of Jaybird Tarah Pro's too. These are alright but I stopped using them for marathon training as my ears sweat like f**king BATHROOM TAPS and you end up forever twisting them about to reseat them. It gets on your t**s so I went for the Aftershokz and keep the Jaybirds for 10km or shorter runs, or Summer railway and/or running commutes.
I have the Jabra Elite 65 thingies. They're alright but feel uncomfortable after a while. Again, more for Summer use on the railway commute. Nice sound from these though, if only they were more comfortable for prolonged use.
Toying with getting a pair of Campfire Audio Polaris II's or perhaps the Andromeda's but I dunno, are they snake oil?
Failing that, the next pair I'd go for would be the WH-1000XM4's, but only IF they are a significant improvement on the XM3's. Which I doubt will happen because they are astonishingly good cans.
I'm probably more in the market for another headphone amp if anything these days as my one at work is knackered.
EDIT: Forgot to add two other pairs of cans in my collection. A set of AKG 518 LE's. I upgraded these to velour pads. The sound is nice from them, but you have to be one of The Borrower's in order to wear them as the headband is tiny! I live with it, even though I look like an idiot wearing them because they sound great.
Also have a set of Ultimate Ears cans. I forget what model they are but they sound whopper and I've kept them for years. They're white with a blue cord if that helps anyone ID them.