Are you more of an earbuds or over-the-ear kind of guy? I think you'll find many people in agreement that Sennheiser are one of the better, more affordable brands. They do have some obscenely priced headphones, but if you're not the biggest audiophile you can get a decent pair off Amazon for under $100. As for earbuds, I loved my Bose IE2 earbuds until I broke them at the gym (don't drop dumbbells on them), but at $99 they are on the pricier side.
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