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Appreciate this doesn't answer your question, but have you tried Comply tips for in ears, they're super comfy?
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I have a set of these which are by far the best gym headphones I've owned. https://www.whathifi.com/sennheiser/pxc-310-bt/review
Compact and don't move about at all with good sound quality and noise cancelling. The downside is they are out of stock so you have to hunt for them second hand (I've actually bought a second pair for when the first die).
Trunkie
aggi
@Bainbridge
Any recommendations for on ear or small over ear wireless ANC headphones?
Need some for the gym which aren’t too bulky. I do my cardio outside of the gym so I don’t have to worry about getting too sweaty.
I hate in ear headphones, they always get uncomfortable for me in about 20 mins regardless of the buds I use.
Comfort is probably number one priority followed by noise cancelling as my gym plays some god awful shite at pretty high volumes.
Got a fairly healthy budget for something that will last.