Recommendations for high-end headphones?

[Tek7]

So I tend to hoard my gift money.

Come January or February, I plan to buy a bicycle and a nice pair of headphones.

I already have good-enough Bluetooth headphones for working out and Klipsch in-ear monitors for miscellaneous purposes, but I want to buy a set of really nice headphones for listening to music. So many of the things I buy myself are either practical or less expensive and I'd like to splurge on an indulgence.

I'm aiming for the $200-$300 price range and I'm soliciting recommendations from the audiophiles in the community.

Any and all input is welcome!

 

[DannyMeister]

Waiting to hear recommendations here... I struggle with headphones.

My current strategy is the most comfortable wired cheapo earbuds i've been able to find for listening on the go (JVC marshmallows) because i tend to break a lot of head phones and hate to keep recharging bluetooth, midrange cans for gaming (Hyper X cloud 2), and SleepPhones for at night.

 

[The Mighty Gerbil]

I've really only had experience with the Sennheiser HD280PRO . I've used them for a couple decades but they've been replaced twice. Sennheiser was nice enough to send new ones after some complaints. Basically the sound quality is fine (though I am not an audiophile) but the, non- detachable, cord gets shorts in it and the pads tend to be eaten apart by body oil. I got them because I wanted closed ear headphones to muffle my computer fans, which are server grade, due to my overcompensating nature on cooling. At 99$ they do the job but I can't recommend them as I have little to compare to. I can say whatever I get next will definitely be closed ear but I think I am in the minority in finding them conformable. I think other people may find them hot.