Best IEM's for Straight Down Wear

I’m new to IEMs as I generally wear Bose QuietComfort ll earbuds to gym and work. However, I just purchased a LP W4 DAC to use with my phone and want to get something else for home use. After scanning through numerous threads here and elsewhere, I settled on Kiwi Ears Cadenza as my first entry and then pre-registered for the Quintet.

My issue with the Cadenza’s is comfort as the over the ear cable hurts after longer listening periods. It’s been some time but now nervous I’ll have the same problem with other IEMs.

That led me to look at Final Audio E5000 but are there others that you might recommend that don’t require over the ear usage or if it does, are comfortable for longer listening sessions (e.g. 3-4+ hours)

Ideally, looking to spend $300 or less and I mainly listen to hip-hop with some folk/alternative sprinkled in. Thank you!

If you like that kind of shell, that is called a “bullet” iem. Here is a BIG list of just those types of iems.

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Sony N3… If you can find one for sale.

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KBear Ormosia can be worn straight down, as well

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