I always listen to music / podcasts when I go to sleep. Always have done. Can’t stand silence (or the wife snoring!)

Currently using some Jays a-jays 1 which sit quite flat in my ear and let me lie on my side. I fancy an upgrade so wonder if anyone could suggest some good sounding in-ear headphones that not only sound great, but will be comfortable enough to listen to while nodding off. $100 or so.

Fan of the Sennheiser SE’s range of in ear headphones.

215’s should be in the right price bracket. Replaceable wire too.

I’ve got the 535’s, they’re stunningly good. Had the 425’s and they were excellent too.

https://www.amazon.co.uk/gp/aw/d/B01N0PZB0H/ref=mp_s_a_1_2?ie=UTF8&qid=1513839106&sr=8-2&pi=AC_SX236_SY340_QL65&keywords=pillow+speaker&dpPl=1&dpID=41Wzfa12hwL&ref=plSrch

That ain’t gonna fit in my ears, or drown out the sound of my wife. (She bought me one with 2 speakers on but the problem is, under the pillow it’s muffled, you need a fair bit of volume and they sound gash)

And those Sennheiser’s are over the ear with a band… I’ve already got some Philips SHP9500s but not great for sleeping with those on.

I used a set of these for a while. Early version (wired) – problem with them was the speakers didn’t sit right over the ears so were never loud enough. They’re on V6 now, so should be better. Hard to say really!
I use some pretty normal in-ear Sennheisers, meself.

I’ve had a set of Acousticsheep bluetooth ones, similar to the ones DezB linked to and find them brilliant for sleeping with – I previously had a set of the wired ones and they were a PITA as I’d wake up in a tangle at least once a night. The bluetooth ones have been great so far although after two years of nightly use one of the speakers is rather intermittent.