OpenFit 2

OP said ANC is a must... You're clowning. I have a set of Openfit 2 and they're great, but they are the literal opposite of noise cancelling. (Sure the upcoming "Pro" is supposed to have some kind of ANC, but I haven't seen those in the wild and whether it works well is an "open" question.)

I’m gonna say something controversial. After trying the Shockz 1 and thinking they weren’t loud enough and then again trying the 2s and having the same issue. I have given up on them. I honestly just bought two cheap pairs of Tozo open ear headphones from Amazon and I love them. They are incredibly comfortable, and quite a bit louder. The louder volume was specially useful for those of you that are into podcasts. Or if part of your run is down bus streets. You can still hear everything outside of you very well but having the option to higher volume is great. I’ve used these for several 50ks and 100ks. Hope this helps!

OpenFit2 by Shockz are absolutely incredible. So comfortable I forget I’m wearing them

I can't use any headphones while running that do not have a strap going around my head or my ears. Currently I use Shokz 2 for running because I like that I can hear outside noise with them. They're great and I would recommend them.

I really enjoy my Shockz openfit 2, but they are out of your price range. I do suggest looking at other open ear buds like it though and find one you like. Those clip on ones are ok also, but they annoy me to wear.