A total of 4 reviews of this product on Reddit.
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Hifiman Ananda I’m assuming you paid $500 for the more more it seems a little out if your budget but they are $300 off on Amazon and seem to have everything your looking for. HIFIMAN Ananda Over-Ear Full-Size Planar Magnetic Headphones with High Fidelity Design Easy to Drive by iPhone/Android Studio Comfortable Earpads Open-Back Design Easy Cable Swapping https://www.amazon.com/dp/B07DJ2ZBB3/ref=cm_sw_r_cp_api_glt_fabc_18AF1GDZWN5N88PCHG3E
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The Ananda is also on sale at Hifiman store front at Amazon and eBay for $599:
https://www.amazon.com/HIFIMAN-Ananda-Full-Size-Headphones-Comfortable/dp/B07DJ2ZBB3/
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For piercing friendly headphones, I think that’ll be kinda hard to find under $100, TBH. An extreme example of a full size headphone that would give you a lot of ear room:
https://www.amazon.com/HIFIMAN-Ananda-Full-Size-Headphones-Comfortable/dp/B07DJ2ZBB3
But if you’re talking earphones/earbuds/IEMs, that’s a different story. The around the ear style buds tend to be most IEMs with their hooks. Do they have to be wireless?
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Amazon has a pair of open box for $524 if anyone is looking.
https://www.amazon.com/dp/B07DJ2ZBB3/ref=cm_sw_r_cp_apa_glt_fabc_T37T89MDF3ZRJJYN20TE