Are there any over-ear wireless headphones that stay cool and have ample clearance for adult ears, and well under a $100 price point?

Have you considered bone conducting headphones? Since they don't actually cover your ears you stay cool, and if you want to block out outside noise they come with ear plugs. I wear mine constantly.

Shokz OpenMove headphones are around $80 https://amzn.to/3LgYCq8

I couldn’t recommend these more! The quality of the sound is top and they’re fucking awesome. Never worry about sweat making my ears slippery or anything. Also the first time you use them it’s kind of a strange experience.

Soundcore Anker Life Q20

With microphone, active noise cancelation, and companion app to mess with eq.

Soundcore Anker Life Q20 Hybrid... https://www.amazon.com/dp/B07NM3RSRQ?ref=ppx_pop_mob_ap_share

This sounds close to $300 headphones I have, but only costs $45 currently. It's a steal.

Bluetooth or can you handle a USB dongle? Logitech G733 headphones are often on sale where I live for €99.99.

I prefer Bluetooth, and would really like to see something that will not allow low security encryption hacking in the initial arbitration, but I know stuff like this level of technical rarely makes it into public documentation.

Thanks for the recommendation. I'll have a look.
- Something like a Sony WH-CH720N? Bluetooth 5.2 (encryption has been default since 4 but I’m sure there are vulns in older versions).

Over the ear that stays cool sounds like a request for open back headphones. But it's difficult to find anything wireless with large breathable earcups for under $100.

Here's an option for fantastic quality and fit but with a cord for under $100.

Here's a pair that's Bluetooth and under $100 but the ear cups can run small and it doesn't breathe very well.

It's difficult to find something so specific with the limiting search criteria. If you open up the budget or remove another requirement such as over ear then the search becomes manageable.

Check out rtings.com

I wear 3m work tunes with gel cushions while working outside year round. They are generally under $70 and I don't notice any significant hest issues around my ears, and that's even when it's 100 degrees outside.

I’d love to see options with ANC if anyone has any.

The ones I’ve tried in terms of a gold standard above $100. I think Bose quiet comfort is up there. Partly because it’s light and not so tight.

I'm using Soundcore Q30, about 80€, ANC, BT, and if you want better sound, there's AUX too. I use them for work too, so several hours without taking them off, and I'm still in love with them.
- This is what I use too. Reasonable price and the ANC is great for blocking out my noisy coworkers.
I've used some "Ausdom" headphones for somewhere between 2-3 years. I think the branding is just a random name generated by whomever paid for a production run at a decent quality Chinese factory. They have Bluetooth with an audio jack bypass, and active noise canceling. The ear covers seem about average ovals. I just have a big head and they barely press against the upper back edge of my earlobes. They are decent quality. The leather like vinyl is nice but just gets a bit warm for extended use. I think I paid $30-$35 on either Amazon or eBay. I would just get some better covers if I could find something compatible. The headphones aren't bad but the vinyl on the ear covers has started falling apart from use.

Is noise isolation or leakage a problem? If not, Grado is the way. If it is, good luck finding any.