I've been wearing 3/4 for a while, and it's time to gauge up again so I got myself some 20.5mm silicone teardrops. They're nice and simple, and I figured that I could wear them for a little bit at a time each day until things were fully comfortable with them, right?
Sadly, not so much. My own dumb fault, though.
I put them in and they were very comfortable. I could tell it was a size up, but I've been weighting my tunnels for a few weeks and there's some spare room to fill. My mistake was popping them in over the weekend and going out for a bike ride which took more time that I had expected. The combination of some extra time and maybe the helmet straps moving things around irritated my ear at the narrow end of the teardrop. For being silicone, it's pointier than I would have expected.
I didn't tear anything, but I did develop an uncomfortable "hotspot" at that peak, so I took them out and went back down to my 3/4 teardrops for another few days until the irritation is gone. I was really hoping to just be able to swap over to them immediately. They are nice looking, and I really dig the shape the elongated teardrop gives my ear.
(Plus, I've got a pair in hot pink to match my team's racing kit!)