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I normally use bud sized headphones for running & cycling, I usually try and get the best ones where I don't have to keep messing with them falling out my ears especially when I'm out & about. You may have to push the boat out in terms of price for better sound wise headphones. You can get wireless ones now but I haven't dipped my toe in that market yet.


I used these ones. I ain't tried cycling in cans yet. Although I do put cans on a string on my back tire.



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Long answer?


It depends on what you’re listening to the most, if it’s music what genre of music, and so on. Different headphones will have different strengths and weaknesses. Do you need to consider other people in the room?


The higher quality headphone the more likely you’re gonna need a dedicated amp to power it to get full use out of it. Most wireless headphones suck and should be met with suspicion and mockery any time someone tells you to buy them. Doubly so if it’s some Apple garbage. 


Short answer?

Phillips SHP9500s at $75.

Sennheiser Massdrop 6XX at $200.


I’d save up and go for the latter.

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I’ll have to save up for some better ones.  I got some wireless JVC. And another pair of cheap gaming headphones that are wired that will break in two weeks. 


But i get the picture. 100-200 for proper headphones. 

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