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I've seen people using them. They look stupid.

Yes. They look awkward.

Seen several people walking around with it, looks pretty stupid imo.

Thats a pretty bad idea....and no I have not, honestly wireless headphones for the most part are overpriced and sound sub par, I am sure there are some decent ones though, cords aren't the end of the world though, why not just get normal headphones?(Maybe with a flat wire if tangling is your reason against them), the Zoro Noontec are really nice for the price and have a flat wire if you don't mind them looking like a Beats ripoff(Sound about 100 times better for less then half the price).

My Saints Row The Third character. That's about it.

I've seen a couple of people using one with their phone.

I dont think I have but then again I am listening to my own music at the time lol. Plus I am not in the city or anything like that.

not headphone and mic, more just headphones but yes i have rarely