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Honestly, I would recommend a good pair of Bluetooth headphones because it is amazing how simply being able to shut out the world can relax a person.
Though I haven't actually found good bluetooth headphones for sub $100. My favorite so far were the Senheiser PXC550 (I think thats it). But mine have gotten chewed by a dog :(. I liked the audio quality, didn't love the touch controls, but the cheap headphones I've gotten to replace them just sound awful.
I am impressed with this pair of Silensys PRO Bluetooth headphones. I got them on sale at Amazon for around ~54.00 USD and they're surprisingly adequate. I don't have the money to justify a better pair. They're even noise cancelling too.
Galaxy buds 2 with a good pair of comply foam earbuds tips clocks in at exactly $100 and has a remarkably solid sound for Bluetooth earbuds. If you want audio quality though you're not going to get it in Bluetooth headphones, there you mostly pay for convenience, but I got some galaxy buds 2 recently and they were fine stock but the foam tips sincerely make a huge difference.
Not headphones but the Samsung earbuds are pretty good and I picked them up for ~60$ on Amazon. I hadn't used earbuds for years and had no idea how good the tech has gotten. Super comfortable, pretty good noise muffling, fancy wireless charging. Makes doing yard work go so fast.
I can't do ear buds because they make my ears actually hurt after wearing them for even as little as 5 minutes
Do you have small ears? That's a serious question by the way. I ask because I have really small ears, so a lot of earbuds are way too large and hurt to wear, but ever since I found ones that have small enough soft tips, it's been a totally different experience
I think I have smallish ear canals which may be the culprit because man do ear buds cause discomfort. I like headphones that completely cover my both my ears. I can wear them all day long without issue.
I definitely prefer the big over-ear ones myself, but I've found that earbuds are just so much more convienient to have with me, and they're also much better at forming a seal for noise cancelation.