Shure - SE215 Pro

Shure 215 all the way. I prefer to swap the foam for the triple flanged off Amazon. They move way less for my ears.

I use the SE215’s similarly. I still bring over ear Bose on long flights for comfort, but I put in the Se215’s when I want to sleep because they’re more isolating and I can move my head to more positions without disturbing them.

The earphones and tips need to be priority one. My guess is even if you plug them directly into the board without the wireless, you will experience bass frequency loss. This could be the drivers in the earphones, but it could also be the seal of the tips of the earphones. Obviously the best way to get a good seal is to get custom impressions and molds made. Sensaphonics will make them for basic headsets like the Shure SE215. They will also make a totally custom driver set for you that is compatible with whatever wireless receiver/transmitter you use. For solutions that don't involve going to an audiologist, I like the Shure SE215 with comply professional series foam tips, when it comes to playing bass live. . Make sure you are really pinching the foam and letting it expand in your ear canal, inserting it properly. It should feel a little snug.

I only remember my first IEM in a traditional sense (people tend to call any in-ear an IEM nowadays, and I had a LOT of these) and it was Shure SE215. It went through a lot, and after several years I cracked one of the shells while trying to remove an aftermarket cable, so I’m no longer using it. Maybe I would’ve hated its sound today but I loved it back then, and I’m sure it still holds up comfort-wise (as I have similarly built E5c which are awesome in that regard).

the thing with chifi iems is that they don't offer nearly as much sound isolation as something meant to use on stage you'd want something like the shure se215 or entymotic er2se. er2's are the better set though imo but only if you're okay with the fit

Love my IEMs. I use Shure 535 and also Shure 215. Both sound great and very happy i made The change

if you value ergonomics and non flashiness, it's hard to beat the Sennheisers or Shure style iems. I've tried a lot, and outside they are imho the best as they are flush with the ear. The Shure se215 are imho even better for small ears. They have a ~3mm nozzle, the transparent casing makes them non attention grabbing. The cable on them sucks though, extremely microphonic. People claim they are outdated audio quality wise though. All i can say is they EQ extremely well (measured).

My Shures have lasted me almost a decade. I've had to replace the cord a few times though.

Chu 2 should be fine, they are reasonably neutral. You might want to consider Shure SE215 (outside of your budget but still) for practice since they are quite comfortable and provide very good passive sound isolation. Alternatively, a proper set of cans can also be nice, something like Sony MDR-7506. I should stress that the last two options I mainly suggest for practicing/tracking and not necessarily for general listening.

I have used plenty of Shures over the years, including the SE215. I'm not a huge fan of the SE215's when playing any instrument because the frequency response is very clearly bass-heavy and the sound is a little muddy. They are great for listening to certain kinds of music, and I can understand why they have been so popular. The frequency response is a lot better on the more expensive Shures like the SE535 or Aonic 4, but overall I think Shure is a lot less competitive in IEMs these days, compared to 10 or 15 years ago.