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If you are impressed how they fit 6 drivers into that small bean shaped shell, wait till you see W80 where the shell is a hair slimmer and stuffed with 8 drivers
As @BKG22 above mentioned, UM56 could be one of the solutions, I covered it in my review HERE, though its advantage is more with creating CIEM-like seal which might or might not help in your case. The advantage of Shure olives tips is shorter stem of the eartips which jams the shell deeper in your ear, and could cause the uncomfort you experiencing where it's rubbing against your antihelix. If you look at the included Westone silicone Star tips, they don't just vary in diameter but also in length. That could control the depth of the shell insertion which can help with a fit. Try the largest star tip with "orange" marking. You don't need to jam it all the way into your ear, even half way in will still give you a good seal of earcanal and it should work as a "spacer" to give your antihelix more room to "breath"See if that will help?
Thanks, @twister6 - and thanks for all your reviews, which are really excellent. I've actually been using the orange star tips, but the housing is still causing pressure against the antihelix of my left ear. It seems there's just not enough lateral width in my left ear to accommodate the earbud.
I may try a pair of CIEMs, though I worry that I might encounter a similar problem. It's a real disappointment since the W60 is genuinely outstanding (as you yourself have said). I auditioned them against the JH 13 v2, Campfire Audio Jupiter, and Noble Audio Savant, and the W60 was the clear winner.
The W80 is an engineering marvel, as you say. I didn't spend long enough with them to get a good feel for the sound (they're out of my price range, unfortunately), but they did impress me.
Yeah, maybe CIEMs is the way to go for you, and if not - perhaps full size headphones as the last resort?